View of Lexington taken from a helicopter.

Lexington is the second largest city in Kentucky, located in the Bluegrass Region. Known as the Horse Capital of the World, Lexington has traditionally been dominated by the horse industry and is also heavily influenced by the University of Kentucky, the state's flagship university and the largest employer in the city. The horse industry has greatly influenced Lexington's culture and scenic beauty; the University of Kentucky and Transylvania University contribute to a college town atmosphere with a richer and more diverse culture than some might expect from its size and location. Lexington's compact central downtown district is surrounded by historic neighborhoods. Lexington is in the heart of the Bluegrass region of Kentucky and is still home to hundreds of horse farms.

Understand

History

Founded in 1775, 17 years before Kentucky became a state, the fledgling campsite was named Lexington when settlers received news of the Battles of Lexington and Concord which had opened the Revolutionary War just a few months prior. (Many people today assume it to be the other way around, since Lexington, Kentucky, is much larger and more well-known than the eponymous Lexington, Massachusetts.)

Lexington was one of the first cities in the country to enact urban growth legislation, controlling lot sizes and requiring suburban expansion to be continuous. This has largely protected the Bluegrass Region's picturesque landscapes from suburban encroachment. Lexington's urban development thus has a fairly sharp dividing line between suburb and countryside, and an interconnected metropolitan network of cities has developed with Lexington at its core, surrounded by a ring of smaller picturesque towns that have benefited from Lexington's prosperity and the auxiliary cities of Frankfort and Richmond, both of which are 40 minutes' drive in opposite directions.

Tourist information

• 1 Lexington Visitors Center, 215 W Main St, Suite 75 (Main St & Broadway, in The Square shops (formerly Victorian Square), across from the Convention Center and Triangle Park. Parking on Main St or Algonquin St, or in The Square garage off Short St), ☏ +1 859 233-7299. M-F 9AM-5PM, Sa 10AM-5PM, Su during summer. 

Get in

By plane

• 1 Blue Grass Airport (LEX  ^IATA), 4000 Terminal Drive, ☏ +1 859 425-3114. A medium-sized regional airport which has service from Allegiant, American, Delta, and United, with daily non-stop service to more than a dozen cities. It deposits passengers directly adjacent to Keeneland Race Course and just a few miles from downtown. There is express bus service by Lextran, once per hour 6AM-6PM. All major brands of car rental agencies have service here, and taxis and hotel shuttles are plentiful. International facilities including customs are available, but no carriers operate scheduled international flights; most passengers will go through customs in a connecting airport.  
• Louisville (Standiford Field SDF ^IATA) and Cincinnati/Northern Kentucky (CVG ^IATA) are larger airports, each about 1½ hours drive from Lexington.

By train

The nearest passenger train service is Amtrak's Cardinal, with stations in Maysville, and in Cincinnati, Ohio (both are about 1½ hours drive); however, there is only service every other day and both trains arrive and depart at night.

By car

Travellers usually access Lexington via one of the two major interstates that arc around the northern and eastern borders of the city. I-64 runs from east to west, connecting Lexington with the largest city in Kentucky, Louisville, to the west. I-75 runs north-south, connecting Lexington with Cincinnati and Knoxville respectively. Neither interstate penetrates into the city. For access to the far side of the city, use New Circle Road (State Route 4), a loop road of which 3/4 is highway-grade, or during non-peak hours you can just take an arterial road through downtown.

The Lexington area is also served by the Martha Layne Collins Bluegrass Parkway, starting near Versailles and ending at I-65 in Elizabethtown, and the Bert T. Combs Mountain Parkway, which starts just east of Lexington and provides access to the Appalachian region.

By bus

The Greyhound station is on New Circle Road on the north side of town, which is ten minutes from the Downtown area.

Get around

That Kentucky accent City names in Kentucky aren't always intuitive. Louisville is pronounced LOOey-vil or LU-vul (never lewis-vil), and Versailles is pronounced ver-SALES (never ver-SAI). Athens is supposed to be pronounced with a long vowel (AY-thens), but many locals pronounce it the same as the Greek capital.

Lexington is a relatively spread out city, though not large. Unless you are mainly visiting the downtown or the university campus (which are within walking distance of each other), you will find that getting around by car is the most convenient method.

Downtown, Main Street divides cross-streets north and south, and Limestone marks east versus west. Addresses downtown usually specify a cardinal direction, which provides a clue to what area of the city it's in.

By bus

Bus service is provided by Lextran, which provides service from the downtown Transit Center to many parts of town and the airport. Most mainlines run every 35 minutes during business hours; others run every 35 minutes only during rush hours, every 60 minutes all other times. Buses run M-F 5AM-midnight, Sa 7AM-midnight, Su 7AM-9PM. Fare costs $1. If you need to transfer between routes transfers are free and can be attained when paying fare, transfers are good for an hour and a half but cannot be used for round trips on the same route. Buses can be tracked in realtime on Lextran's MyStop website or from Google Maps.

Downtown

Downtown Lexington is compact and easily navigated by foot or bicycle, but the most typical way to get around is by car. Cars can be rented at the airport or at several locations in the city. Taxis should be called in advance as they are not easily hailed on the street. There is a taxi stand in front of the airport. From 6PM to 6AM a taxi stand operates at the corner of Main and Upper Streets, next to the old courthouse.

By car

Lexington's roads form a wheel-and-spokes pattern. Arterial roads radiate from downtown, and New Circle Road (KY-4, sometimes called "Circle 4") forms a circle around the inner city. New Circle Road, an early experiment in urban circumferential expressways, was built before current zoning rules, so that about 1/4 of it is developed with commercial usage, while the rest is 55-mph freeway with on/off ramps. The radial roads are mostly named after the neighboring towns they lead to (e.g. Nicholasville, Richmond, Winchester), although as you approach downtown they take on a different name (e.g. Limestone, Main). Directions in Lexington will frequently start with "Take New Circle to ____ Road (one of the arterials), then turn north/south...."

Man o' War Boulevard forms a half-circle further outside from New Circle Road; however its lower speed limit and abundance of traffic lights make it less ideal for circling the city.

Like any city, Lexington's traffic can be challenging during rush hours. Nicholasville Road has reversible lanes to help the flow. Be careful and aware of the lights as they change throughout the day to accommodate traffic and rush hour. A green arrow indicates appropriate lanes for driving; white turn only arrows indicate a center turning lane; a red X indicates lanes in use by oncoming traffic. If possible, try to avoid traveling north on Nicholasville Road during the evening rush hour, as most lanes switch to southbound traffic to allow people to exit downtown. Be aware of driving near the University of Kentucky on basketball or football days. Downtown can be quite congested when UK plays at Rupp Arena, and Tates Creek Road and Nicholasville Road both move very slowly when UK plays at Kroger Field.

Most of the major arterial streets have multiple names, especially as you approach downtown (Nicholasville Road becomes Limestone; Harrodsburg Road becomes Broadway; etc.). This is also true of many smaller city streets (Winslow Avenue becomes Avenue of Champions, which becomes Euclid Avenue, which becomes Fontaine Road). When you ask for directions, many locals may not know exactly what the street is called where you're going, just remember that the same road may be called any of those at your destination.

Almost all of the arterials, and many smaller roads, are also numbered U.S. Highways or Kentucky State Roads, but no one refers to them by number. The sole exception is New Circle Road, which is KY-4 and sometimes called "Circle 4", but more often called "New Circle".

See

• 1 Ashland (Henry Clay Estate), 120 Sycamore Rd (off Richmond Rd), ☏ +1 859 266-8581. Tu-Sa 10AM-4PM, Su 1-4PM; Jan closed, Feb only open for groups. Home of the famous Kentucky Senator Henry Clay, set near downtown Lexington. Beautiful park surrounding the home accessible even if you do not wish to take a tour. Adults $10, children ages 6–18 $5, children 5 and under free.  
• 2 Boone Station, 240 Gentry Rd (Richmond Rd 1.5 miles past I-75, then left on Cleveland Rd, right on Gentry Rd, park is on the left after 0.4 miles), ☏ +1 859 263-1073. Apr-Oct. Boone Station State Historic Site is on 46 beautiful acres in Fayette County. Daniel Boone (1734-1820), known for his role in the exploring and settling of the Kentucky frontier, decided that the settlement of Boonesborough had become far too crowded. In December 1779, Boone and his family established Boone's Station. The park features a 1-mile trail and a grave site where several members of the Boone family are buried. 
• 3 Hopemount, 201 N Mill St (downtown, in historic Gratz Park, 1 block from Broadway & 2nd St), ☏ +1 859 233-0362. W-F 1PM-4PM, Sa 10AM-3PM, Su 1-4PM; weekend hours subject to change. Built by the first millionaire west of the Alleghenies, John Hunt-Morgan, the house showcases early Kentucky furniture, 19th-century paintings, and antique porcelain. The Alexander T. Hunt museum featuring Civil War memorabilia is located on the second floor. The house was built in 1814 when Lexington was known as the "Athens of the West." Adults $7, seniors $6, students and children under 12 $4.  
• 4 The Kentucky Theatre, 214 E Main St (downtown, 2 blocks from Limestone), ☏ +1 859 231-7924. A historic two-screen cinema with restored architecture and beautiful interior murals located downtown on Main Street. Its schedule tends to emphasize foreign, independent, and art films, plus occasional concerts and panel discussions at the premiers of controversial films. During the Summer Classics Series every Wednesday night a classic film is shown. The theatre has an offbeat side as well, and raucous midnight showings of movies like The Rocky Horror Picture Show draw crowds of nearby university students, adults, and teens every weekend. Tickets $7.50; children/seniors and before 6PM $5.50.  
• 5 Lexington Public Library, 140 E Main St (downtown, at Limestone), ☏ +1 859 233-0362. M-Th 9AM-9PM, F 9AM-6PM, Sa 9AM-5PM, Su 1-5PM. The Central Library is worth a quick look for its art installations. Rose-colored granite covers the facade, and the airy atrium houses a 5-story-tall Foucault pendulum, which tells time using the rotation of the Earth. In front, Phoenix Park offers some nice greenery and fountains, and a small statue of a Bedouin on a camel marks the "zero milestone", the point from which all distances to Lexington are measured. However, the view is hampered somewhat by a building across the street.  

Mary Todd Lincoln House, childhood home of Pres. Lincoln's wife

• 6 Mary Todd Lincoln House, 578 W Main St (downtown, 3 blocks NW of Broadway), ☏ +1 859 233-9999. Tours mid-March–Nov: M-Sa 10AM-3PM. The two-story girlhood home of Abraham Lincoln's wife, and the nation's first shrine to a First Lady. The 14-room house contains period furniture, furnishings from the Todds and Lincolns, and family portraits. Adults $15, children 6-12 $6, children under 6 free.  
• 7 Triangle Park (especially at night), 400 W Main St (downtown, in between Main St, Vine St, & Broadway, adjacent to the Lexington Convention Center). Year-round; fountains shut off in winter. Enjoy slipping off your shoes or sandals in the summertime and wandering in the step-like fountains that ring the backbone of this park. Get plenty of pictures of the illuminated fountains against the Lexington Convention Center. Events throughout the year include summer movies on alternate Friday nights, a winter ice skating rink, and occasional concerts. Cross the street and talk to the concierge at the Hilton Hotel to book a horse-drawn carriage tour of downtown. (updated Jan 2018)
• 8 Waveland State Historic Site, 225 Waveland Museum Ln (near Nicholasville Rd & Man o' War Blvd), ☏ +1 859 272-3611. M-Sa 10AM-5PM, Su 1-5PM. Tours and museum closed Jan-Mar, but grounds open year-round. Built in 1848 by Joseph Bryan, a grand-nephew of Daniel Boone, the Greek revival home preserves 19th-century plantation life in Kentucky with acres of hemp and grain. The smokehouse, icehouse and slave quarters still stand as outbuildings. Adults $7, seniors $6, students $4, children under 6 free.  

Do

Despite the relatively small size of this South-North straddling city, Lexington offers a surprisingly delightful palette of interesting activities. Whether you choose to explore some of the world-class and stunning horse farms ringing the city, hit up some of the surprisingly upscale shopping venues, take in a play at the Downtown Arts Center or the Lexington Opera House, tour the oldest university west of the Allegheny Mountains (Transylvania University), catch an insanely popular UK basketball game (Rupp Arena) or sample one of the myriad great restaurants that have sprung up all over town, you can be sure your experience here will not be a bland one.

Local indie magazine ACE Weekly (published weekly) is full of write-ups and advertisements for local events; it is free and available throughout the city.

• 1 Big Ass Fans, 2348 Innovation Dr, ☏ +1 859 233-1271, toll-free: +1-877-BIG-FANS (244-3267). Usually Tu 9AM-11AM depending on tour; see website for availability. Manufacturer of large industrial ceiling fans (up to 24 ft (7.3 m) in diameter) and a range of residential fans and lighting products. Founded as HVLS Fan Co., many customers called asking for the company that makes "those big-ass fans". The owner decided to change the name to Big Ass Fans, which stirred up a bit of controversy when he painted the company's name along with a giant donkey's rear end (named "Fanny") on the side of the building. Local residents protested at first, and the airport refused to accept advertising from the company. But eventually people warmed to the new name, and the airport now has a Big Ass Fan installed near the security checkpoint. You can tour their headquarters, R&D facility, and production facility. Free. Reservations required. (updated Jul 2019)

Bourbon

See also: Kentucky Bourbon Distilleries Tours

Kentucky is the proud home of bourbon whiskey, and Lexington is an ideal home base for exploring the Kentucky bourbon trail. Four of the distilleries on the bourbon trails are in town:

• 2 Barrel House Distilling, 1200 Manchester St, Building 9 (Old Frankfort Pike, in a gravel parking lot), ☏ +1 859 259-0159. W-F noon-5PM (tours at 15 minutes past the hour 12:15-4:15PM), Sa Su 11AM-3PM (tours 11:15AM-2:15PM). A micro distillery, part of the Kentucky Bourbon Trail Craft Tour. Their history ties back to the James E. Pepper Distillery, the former owner of their building 50 years prior. Current products include a vodka, moonshine, rum, and bourbons. Tours free (samples of vodka, moonshine, and 1 other spirit) or $5 (samples of all spirits, plus souvenir shot glass). (updated Oct 2015)
• 3 Bluegrass Distillers, 510 W Sixth St #165, ☏ +1 859 253-4490. Tu 10AM-noon, 1-5PM, W-Sa 10AM-5PM, Su noon-5PM. Tour $5. (updated Jul 2019)
• 4 James E. Pepper, 1228 Manchester St, #100 (Enter parking lot off Manchester Rd (Old Frankfort Pike). Go to far end of parking lot; distillery has smokestack and "1776" water tower. Entrance on the patio.). Summer (Apr-Oct) W-Sa 10:30AM-3:30PM, Su noon-4PM; winter (Nov-Mar) W-F 12:30PM-3:30PM, Sa 10:30AM-3:30PM, Su noon-4PM; tours on the hour. Tour $20, veteran $10, military and children under 10 free. (updated Jul 2019)
• 5 Town Branch Distillery (Alltech's Lexington Brewing & Distilling Company), 401 Cross St (near Versailles Rd / W High St & W Maxwell St), ☏ +1 859 255-2337, TownBranchTours@alltech.com. M-Sa 10AM-5PM, Su noon-5PM; tours every hour, last tour at 4PM; Jan-Feb no tours on Tuesdays. Touring Town Branch, you'll get a double-header of beer and whiskey. From its roots as an agricultural company started by yeast expert Dr. Pearse Lyons, Alltech began brewing beer with the intention of making slightly more than its employees could drink. Ten years later, they now produce 5 beers and 3 spirits and are Kentucky's largest brewery, working 24 hours a day to keep up with demand, 80% of which is for their signature Bourbon Barrel Ale. Tour $8.50, 18 and under free. (updated Mar 2015)

Five others distilleries on the bourbon trail are with 20–25 miles, or about 30–45 minutes' drive, listed below under § Go next.

Festivals

• Woodland Art Fair (at Woodland Park). Sa-Su around Aug 21 (see website). See 200 juried artists offering every type of folk art and craft you can think of, including painting, woodworking, and stuffed animals. Enjoy live music and entertainment. Your children can work on their own crafts in the Kid Zone. Free admission. 
• Festival of the Bluegrass (at the Kentucky Horse Park campgrounds). First full weekend of Jun, Th-Su (see website). Outdoor music festival held every year at the beautiful Kentucky Horse Park. Great live music from bluegrass legends to newgrass pickers, fun shopping, and great activities highlight this family friendly event. 4-day ticket $85, 1-day ticket $10-45, 4-day youth (13-17) ticket $45, kids 12 and under free. 

Horses

Lexington isn't called the "Horse Capital of the World" for nothing. The horse industry is Lexington's traditional and most famous trade, and many beautiful old farms are worth a look.

• 6 Kentucky Horse Park, 4089 Iron Works Pkwy (7 miles north of the city. I-75 exit 120, or take Newtown Pike or Georgetown Rd for a scenic route), toll-free: +1-800-678-8813. 9AM-5PM daily; in winter (Nov-Mar) closed M-Tu and some holidays. The Park is basically a tourist-oriented horse farm and offers a museum, nice walks, views of famous racehorses, and lots of bluegrass (the plant, not the music). There are various horse shows throughout the day, as well as extra activities including horseback and pony rides. The Park is also the host of some very large horse events. Probably the most high profile annual event is the Rolex Kentucky Three Day, a major eventing competition which takes place every April. The park also hosts the National Horse Show in October/November, and hosted the 2010 FEI World Equestrian Games, the first time they were held outside of Europe. These horse trials are also used as Olympic selection trials so you can expect to see some world class horses and riders. Adult $16 summer/$10 winter; children 7-12 $8 summer/$5 winter; children 6 and under free. Parking $3/day, special event parking $5/day.  
• There are many horse farms clustered north and west of Lexington. Several companies do daily van tours of private farms, either on guided or customized tours (get referrals from the Lexington Visitor's Bureau). Tour itineraries vary daily and seasonally, but a typical tour might include a stop at one or more farms where you can get close enough to touch some horses (if the conditions are right: no petting young horses that aren't calm enough, or ones that are being taken for training or other duties), a stop at Keeneland race track and/or the Kentucky Horse park, and a scenic drive past many other famous and ritzy farms like Calumet. You can also book your own visits directly. However, these are all working farms, so if you're visiting independently, call in advance to check availability and make arrangements.
  • Blue Grass Tours, ☏ +1 859-233-2152. Spring-fall, M-Sa 9AM and 1:30PM, Su 1:30PM. Tours last 3 hours. Adults $35; children 12 & under $25; seniors $32. Minimum 4 guests. 
  • Horse Farm Tours Inc., ☏ +1 859 268-2906, toll-free: +1-800-976-1034. 8:15AM and 12:45PM daily. Tours last 3½ hours. Adults $35 (in winter $40); children under 12 $26; seniors $33. 
  • Thoroughbred Heritage Horse Farm Tours, ☏ +1 859 260-8687, toll-free: +1-800-808-9533. 8:45AM and 12:45PM daily. Tours last 3 hours. Adults $35 (in winter $40); children 12 & under $25; seniors $33. Prices may vary during peak times (such as Kentucky Derby) or off season (winter). 
  • Unique Horse Farm Tours (departs from the Kentucky Horse Park at the Visitor Information Center), toll-free: +1-800-678-8813 ext 4225. 9:15AM, 12:15PM, and 3:15PM daily. Tours last 2 to 3 hours. Adults $35; children 12 & under $15. 
• 7 Keeneland Race Course, 4201 Versailles Rd (at Man o' War Blvd, 1 mile west of New Circle Rd), ☏ +1 859 254-3412, toll-free: +1-800-456-3412. Live races Apr and Oct. Enjoy horse racing in a "days-gone-by" setting. The movies Seabiscuit (2003), Dreamer (2005) and Secretariat (2010) have been filmed at Keeneland, which prides itself on maintaining racing traditions in a facility that has changed little over the decades: for example, it didn't install public address speakers until 1997. Keeneland hosts live thoroughbred races only two months a year, with the Spring meet in April and Fall meet in October, but they welcome visitors year round (you can use online or print maps to explore the grounds for free, or book a tour). During races you can choose your level of comfort near the track (general admission, grandstands, or nicer indoor rooms), or tailgate in the free parking lot while watching races on a jumbo TV and wagering. The feature race of the Spring meet is the Toyota Blue Grass Stakes, a prep race for the Kentucky Derby. When its live races are not in session, entry is free; you can explore the stadium and walk right up to the race track, watch other races broadcast from around the world, or attend events like the yearling horse sales, where many young stallions command price tags in the millions. Buyers include local horse farms and bidders from Europe, Saudi Arabia, and Dubai. Year-round tour $10/person, 12 and under free; special tours $30-50. During race meets, general admission $5, grandstands $8-20, indoor rooms $15-65, but if you don't put some money on your favorite horse or jockey, you're missing the point. BETologists are around to explain betting for beginners and experts alike. Cash bets only (ATMs are available); minimum bet $1 (win, place, show, exactas). Parking free-$5. The tradition at Keeneland is to dress-up a bit, so no jeans or T-shirts; most indoor rooms enforce dress codes ranging up to "suit or jacket required". Outdoors, bring a coat and hat, too, as it can be cold and windy in April and October. (updated Dec 2016)
  • The Keeneland Library, ☏ +1 859 254-3412, toll-free: +1-800-456-3412. M-F 8:30AM-4:30PM; during race meets and sales also Sa 9AM-12:30PM; closed holidays. A reference library full of books, photo negatives, and newspaper articles about the Thoroughbred horse and horse racing. There's a small museum area at the front as well as various art inside the library. Free. (updated May 2015)
• 8 The Red Mile, 1200 Red Mile Rd (off S Broadway), ☏ +1 859 255-0752. Live races Aug–early-October. The Red Mile hosts harness racing, where horses pull a two-wheeled cart. The one-mile track is made of red clay, whence the name. Admission $2 during race meets. 

Outdoors

• 9 Legacy Trail, ☏ +1 859 425-2255. When ultimately completed, this walking and biking trail will extend 12 miles from the east end of downtown to the Kentucky Horse Park. The majority of the trail is complete and begins at the North Lexington YMCA (381 West Loudon Ave). Other trail heads are located at Coldstream Park off of McGrathiana Ave, and the North trail head on Old Ironworks Pike across from the campground at the Kentucky Horse Park. 

View from Kentucky River overlook in Raven Run Nature Sanctuary

• 10 Raven Run Nature Sanctuary, 3990 Raven Run Way (12 miles southeast of downtown), ☏ +1 859 272-6105, naturalist@lexingtonky.gov. 9AM-5PM, trails close at 4:30PM. A 734-acre park along the Kentucky River Palisades in Fayette County. Great wildflower viewing in the spring. 
• 11 The Arboretum, 500 Alumni Dr, ☏ +1 859 257-6955. Dawn-dusk. A 100-acre botanical garden located next to the University of Kentucky. This park is jointly owned by the city and university. Two miles of walking paths meander through representations of different areas of the state. 

University of Kentucky sports

Alumni pride Film actress Ashley Judd is a UK alumna, and a fierce Wildcats fan. She regularly attends basketball games every season, often sitting in the student section. She also helped start a series of posters for UK's ice hockey club team. Designed as a fundraiser, the poster had the team's 1998-1999 schedule over a photo of Judd wearing nothing but a hockey jersey. (Judd, who had a cousin on the team at the time, provided the photo for free.) The posters sold like hotcakes, the "coolcats"' raucous midnight games became even more popular, and the poster became an annual tradition, each year featuring a different good-looking celebrity Kentuckian.

The UK Wildcats are immensely popular throughout the state (with the partial exception of the immediate Louisville area, where loyalties are divided between UK and its rival University of Louisville) and even more so in Lexington itself. Even if you're not a sports fan, you'll know when it's gameday as the entire town will be dressed to support Big Blue.

• 12 UK basketball, Rupp Arena, 430 W Vine St (attached to the Lexington Convention Center downtown). The Kentucky men's basketball team, one of the most storied programs in all of college sports, boasts eight NCAA championships (including in 2012), an undefeated regular season in 2014-15, and leads the NCAA with more than 2,000 all time wins. The team coach (John Calipari since 2009) inevitably enjoys celebrity status around town. Tickets $35–46 face value, but expect to pay illegal scalpers much more, especially for games against quality opponents. (updated May 2017)
• 13 UK football, Kroger Field, 1540 University Dr. The football program has enjoyed something of a renaissance, although it continues to struggle to establish itself in one of the country's most competitive football conference. Nonetheless, the team frequently sells out the on-campus Kroger Field (formerly Commonwealth Stadium), at least for SEC home games and the major rivalry game with University of Louisville (hosted by UK in odd-numbered years). Tickets $35–$46 face value, but expect to pay illegal scalpers much more, especially for games against quality opponents. (updated May 2017)

Buy

Keep an eye out for merchandise marked "Kentucky Proud", which marks it as a participant in Kentucky's buy-local initiative.

• Liquor Barn. The supermarket-sized stores of this local chain make it a good stop for travellers, with gourmet bakery, cheese, and deli items, and a large case of Kentucky Proud foods. Of course, the many aisles of liquor, wine, and beer are also great if you want to take home a special bottle of bourbon or some hard-to-find beers. 

There are several major shopping areas in Lexington.

• Nicholasville Road, particularly between Man o' War Boulevard and New Circle Road, is a major center for shopping, with several malls and many smaller stores.
  • 1 Fayette Mall (Nicholasville Rd. & Reynolds Rd., just south of New Circle Road). The largest mall in the state, anchored by Macy's, JCPenney, Dillard's, H&M, and Dick's Sporting Goods.  
  • Adjacent 2 Lexington Green strip mall features Joseph-Beth Booksellers, 161 Lexington Green Cir #B (in Lexington Green, at Nicholasville Rd & New Circle Rd), ☏ +1 859 273-2911. M-Th 9AM-10PM, F-Sa 9AM-11PM, Su 11AM-9PM. An independent bookstore with an impressive selection of books in their cavernous, sunlit interior. Authors on book-signing tours are practically guaranteed to stop at Jo-Beth, and they often have extra copies of recently signed books available. 
  • Artique, 161 Lexington Green Cir #B24 (in Lexington Green, adjacent to Joseph-Beth Booksellers), ☏ +1 859 272-8802. M-Sa 10AM-9PM, Su 11AM-6PM. Award-winning craft art pieces from artists across America. Whether fashionable or functional, thousands of unique creations of wood, glass, metal, jewelry, and more are waiting for you to discover them. 
• 3 Hamburg Pavilion (Man o' War Blvd & Sir Barton Way, just off I-75 exit 108). Hamburg is a "power center", an open-air, auto-oriented shopping district with several "big box" anchor stores and many smaller shops like Victoria's Secret and the Black Market. An accompanying residential area sprang up with the shopping complex just at the turn of the millennium. The area continues growing daily; expect plenty of traffic.  
• 4 The Square (formerly Victorian Square) (Main St & Broadway, across from Triangle Park). A block of renovated Victorian buildings that was re-purposed as an entertainment area. Located in the heart of downtown, it is connected to the adjacent hotels and business complexes by raised pedways. Containing primarily upscale clothing, jewelry, and art boutiques, it is worth a visit as much for the interior design as the shopping opportunities. It also houses the Lexington Visitors Center. 
  • The Square also connects via pedway to the Lexington Shops in the belly of the Lexington Convention Center, with the Kentucky Proud Market, a UK Memorabilia store, and more.
• Maxwell/High is streets bordered on the west and north by Maxwell and High streets respectively, containing a myriad of small, primarily youth-oriented independent boutiques as well as several restaurants. Small boutiques includes the Black Market Boutique, Helen's Boutique, Lucia's, Calypso, Mod Boutique, John's Walk Run Shop, and ILO.
• South Lime/Campus Area The bordering downtown campus area features many locally owned restaurants and small locally owned stores. Stop by CD Central for used CDs, new albums, DVDs, wall sized posters, T-shirts from major and local artists, and more. Sqecial Media features many unique gifts from magazines, eclectic books, jewelry, candles, incense, trinkets, and journals. ReBelle is a one of a kind shop featuring all kinds of yarn, locally made clothes, and jewelry.

Eat

Lexington is home to an astonishing number of independently owned restaurants at all price levels. The city's college town atmosphere and affluent lifestyle contribute to this relatively small metropolitan area's great culinary offerings. Chain restaurants, typical in most American cities and towns, can be found here, as well as a great number of privately owned and operated establishments.

Kentucky cuisine to look for includes the Hot Brown, an open-faced sandwich of turkey, bacon, and cheese sauce; burgoo, a traditional game stew with as many variations as there are people who make it; beer cheese, a spicy spread of cheddar cheese and beer; and bourbon balls, a sort of chocolate and bourbon truffle with pecans.

Note that smoking is banned in restaurants, bars, and many public buildings in Lexington.

Budget

Downtown

• 1 Third Street Stuff & Coffee, 257 N Limestone (just off Transylvania University campus), ☏ +1 859 255-5301, thirdstreetstuff@gmail.com. M-Sa 6:30AM-11PM, Su 7:30AM-11PM. This coffee shop also serves up unique sandwiches. It's a hip cool hang out with an artistic vibe and store inside. (updated Nov 2019)
• 2 Bourbon n' Toulouse, 829 E Euclid Ave (at High St), ☏ +1 859 335-0300. M-Sa 11AM-10PM, Su 11AM-9PM. This popular eatery brings a bit of New Orleans to the Bluegrass. The way Bn'T works is quick and painless: pick what you want from the day's selections listed on the chalkboard menu, then order and pay at the register. Not sure what you want? Just ask them for some samples. Standards include Cajun and Creole classics like étouffée, gumbo, and jambalaya, as well as barbecue sandwiches and a few unique creations. Vegetarian and gluten-free options available. All plates are $7.50 (tax included); half-orders are $5.50, and are still plenty of food. (updated Nov 2019)
• 3 Charlie Brown's, 816 E Euclid Ave (just off UK campus), ☏ +1 859 269-5701. M-Th 11AM-1AM, F-Sa 11AM-2AM, Su noon-midnight. Hip sandwich restaurant where patrons lounge in sofas and armchairs while chatting in the permanently low lighting. Bookshelves line all four walls and are crammed with old hardbacks; patrons may take any book they please as long as they replace it with another. Virtually all sandwiches are $6.50. 
• 4 Tolly-Ho, 606 S Broadway, ☏ +1 859 253-2007. 24/7; closed some holidays and special events. A typical college town "greasy spoon" restaurant, "The Ho," as it is called by students, serves classic items like hamburgers (from smallest to largest, the Tolly-Ho, Super Ho, and Mega Ho); shakes; Epic Fries with chili, bacon, jalapeños, and cheese; and the ever-popular cheddar tots. It gets extremely crowded when the bars close around 2:30AM and the line stretches out into the front parking lot. Burgers $2.49-7.19, or plain for just $1.25; fries $1.89-5.99; cheddar tots $3.10; milkshakes $2.92-3.71. Be sure to mention if it's your first time. 

Around town

• 5 Brontë, A Novel Bistro (Café at Joseph-Beth), 161 Lexington Green Cir #B (inside Joseph-Beth Booksellers), ☏ +1 859 273-2911. M-Th 9AM-10PM, F 9AM-11PM, Sa 8AM-11PM, Su 9AM-9PM. This café is an excellent spot for breakfast or lunch, with a monthly menu of salads, sandwiches, and other entrées inspired by novels or cookbooks available in the bookstore. 
• Gumbo Ya Ya, 294 E Brannon Rd, Nicholasville, ☏ +1 859 252-9292. M-Sa 11AM-9PM, Su 11AM-8PM. Cajun like no other. Menu changes every week, but standards like White Chile, Gumbo, Jambalaya are usually on, as well as a couple of their good vegetarian or vegan options. If you are lucky, you can end up there on a day they are dishing up Pazole Stew or Jambalaya Ya Ya. And their famous Yatwich is something to surprise you: sort of a turkey-based sloppy joe with a lemony kick. Plate of rice or pasta with one sauce $6.75, with two sauces $7.25; the hungry can get a super size for $7.75. (updated Mar 2018)
• 6 Mousetrap, 3323 Tates Creek Rd (in the Lansdowne Shops near New Circle Rd), ☏ +1 859 269-2958. Serves up sandwiches, soups, and other delectable items available behind a huge glass display case. Always made right in front of you. When you're finished dining you can revel in the shopping part of the store that includes cookware, chocolates, homemade bread, and more. 

Mid-range

Downtown

• 7 Columbia's Steak House, 201 N Limestone, ☏ +1 859 253-3135. A long time favorite in Lexington. With several locations, the original one downtown is the place to be. Back in the restaurant's heyday, professionals and students would line the block waiting for a table. Columbia's is famous for their "Nighthawk" special, which includes an 8-ounce tenderloin smothered in garlic butter, generous baked potato, a Diego salad, and homemade rolls with honey butter. 
• 8 Joe Bologna, 120 W Maxwell St (between S Upper St & S Limestone), ☏ +1 859 252-4933. A moderately-priced Italian located inside an old building that has been home to a church and a synagogue, complete with stained-glass windows and raised pulpit (now a small bar). The square pizza at Joe B's is a tradition. Also, the bread stick is awesome—basically an over-sized breadstick accompanied by melted garlic butter. 
• 9 Oasis, 837 Chevy Chase Pl (near E High St & Euclid Ave), ☏ +1 859 269-6440. One of the best Middle Eastern places in town! Their Chicken Shwarma is served in a generous portion (that is great for leftovers) that is accompanied by your choice of salad. The hummus and pita is excellent as well. The lunch buffet is expansive with many dishes to choose from sure to satisfy anyone. Worth the trip! 

Around town

• 10 Bella Notte, 3715 Nicholasville Rd (just south of Fayette Mall), ☏ +1 859 245-1789. Su-Th 11AM-10PM, F-Sa 11AM-11PM. This local Italian restaurant is inspired by trattoria, gathering places for family and friends. The dimly-lit interior features stone floors and greenery throughout the rooms. 
• 11 Columbia's Steak House, 2750 Richmond Rd, ☏ +1 859 268-1666. 
• 12 El Toro, 1917 Nicholasville Rd (just north of Southland Dr), ☏ +1 859 277-2255. Su-Th 11AM-10PM, F-Sa 11AM-10:30PM. A classic Mexicana restaurant with all your favorite dishes that serves up delicious food in which seems like mere minutes after you order. A friendly staff and quick service make this a enjoyable trip. (updated Nov 2019)
• Ramsey's. M-F 11AM-11PM, Sa-Su 9AM-11PM. This "meat and three" is a favorite for Southern cuisine, and is frequently filled to capacity. All ingredients are obtained from local farmers. Breakfast is available all day every day. Breakfast mains $10-14; Lunch mains $9-10; Dinner mains $9-12. 
  • 13 Ramsey's, 4053 Tates Creek Center (at Man o' War Blvd), ☏ +1 859 271-2638. 
  • 14 Ramsey's, 3090 Helmsdale Dr (Andover, near Hamburg Pavilion), ☏ +1 859 264-9396. 
  • 15 Ramsey's, 4391 Harrodsburg Rd (past Man o' War Blvd), ☏ +1 859 219-1626. 
  • 16 Ramsey's, 151 Zandale Dr, ☏ +1 859 259-2708. 
• 17 Winchell's Restaurant and Bar, 348 Southland Dr, Lexington, KY 40503. Combination restaurant and sports bar. Arguably the best place in Lexington to get a hot brown. (updated Apr 2024)

Splurge

Downtown

• 18 Dudley's on Short, 259 W Short St, Suite 125 (near Upper St), ☏ +1 859 252-1010. Lunch daily 11AM-2:30PM; midday menu daily 2:30PM-4PM; dinner Su-Th 5:30PM-10PM, F-Sa 5:30PM-11PM. An old mansion that has been converted into a posh commercial complex. Dudley's occupies several rooms and serves American fare. (updated Jul 2019)
• 19 Le Deauville, 199 N Limestone (at W Second St), ☏ +1 859 246-0999. M 5PM-9PM, Tu-Th 5PM-10PM, F-Sa 5PM-11PM. Lexington's downtown French bistro is a convivial place, given to conversation and good food. It shares a name with the city's stylish sister town in Normandy, and it's become quite a culinary destination for folks in the area. 

Around town

• 20 Asuka Japanese Grill & Sushi, 360 E Brannon Rd, Nicholasville (Near Man O' War and I-75), ☏ +1 859 543-0010. 11ː30AM-2PM, 5-10PM. Chefs entertain at this sizable, modern Japanese steakhouse featuring hibachi fare & sushi rolls. (updated May 2017)
• 21 Hall's on the River, 1225 Athens-Boonesboro Rd, Winchester. This classic southern seafood restaurant may be a bit far from town, but the scenic drive down KY-418 and location on the Kentucky River make it worthwhile. Try their famous beer cheese for an appetizer, and enjoy their excellent seafood selection, or play it safe with the very large "Kentucke River" Hot Brown. 
• 22 The Kentucky Castle, 230 Pisgah Pike, Versailles (near Versailles Rd & Bluegrass Pkwy), ☏ +1 859 256-0322. Th-Sa (hours unknown); breakfast 8AM-10:30AM; tours 11AM, noon, 2PM, 5PM, 6PM. Everyone in Lexington knows about the extravagant (and most would say, eccentric) castle on Versailles Rd. Built by a newlywed couple in 1969, they soon divorced and the castle sat empty and unsold for decades. Finally, new owners and zoning changes allowed the castle to open in 2008 as an upscale bed-and-breakfast, and now as a farm-to-table restaurant, allowing the public their first real chance to see inside the castle walls. They also offer a guided tour of the ornately-decorated first floor and the grounds inside the castle wall, followed by a buffet. Dinner mains $18-47. Breakfast $11-18. Tours lunch $35/person, dinner $55, 2PM (no food) $20. (updated Jan 2018)
• Malone's. 11:15AM-10:30PM daily. A local steakhouse chain that "imports" its USDA Prime Beef straight from Chicago. One of the most favored restaurants by Lexingtonians, and now planning to open a Louisville location in 2020. All locations also have a sports bar and sushi restaurant. 
  • 23 Malone's, 3347 Tates Creek Rd (in Lansdowne Shops, near New Circle Rd), ☏ +1 859 335-6500. 
  • 24 Malone's, 3735 Palomar Centre Dr (in Palomar Centre, at Harrodsburg Rd & Man o' War Blvd), ☏ +1 859 977-2620. 
  • 25 Malone's, 1920 Pleasant Ridge Dr (near Hamburg Pavilion), ☏ +1 859 264-8023. 
• 26 The Merrick Inn, 1074 Merrick Dr (off Tates Creek Rd & New Circle Rd), ☏ +1 859 269-5417. M-Th 5:30PM-10PM, F-Sa 5:30PM-10:30PM; cocktail lounge open till 1AM. Boasts a classy restaurant nestled within the ritzy gated community "Merrick Place". Main courses $16-$32. Reservations recommended. 

Drink

Nearby Winchester is home to a regional soft drink called Ale-8-One. The soda was developed in the 1920s after major drinks like Coca-Cola were already established, hence the name, which is a pun on "a late one" (as in "the latest thing"). The ginger- and citrus-flavored soda has some passionate fans, and for most of its life was only available in Central and Eastern Kentucky, but since the 2000s you can find "Ale-8" in surrounding states and in Cracker Barrel restaurants nationwide.

Coffeeshops

• 1 Coffee Times Coffee House, 2571 Regency Rd (near Nicholasville Rd & New Circle Rd), ☏ +1 859 277-9140, toll-free: +1-877-673-0577. M-Th 7:30AM-9PM, F-Sa 8AM-11PM, Su 11AM-5PM. Excellent selection of whole-bean coffee and loose-leaf tea for sale or drinking on site. 

Bars

If you're at all interested in bourbon, consider making a daytime trip to explore some of the nearby bourbon distilleries, listed in the Do and Go next sections.

Downtown

• 2 Country Boy Brewing, 436 Chair Ave. Tasting room for one of Lexington's up and coming breweries. Their "Shotgun Wedding" brown ale is their most popular brew, but they always keep it interesting with other options. (updated Mar 2018)
• 3 Chase Brewing Company, 266 Jefferson St. Located in the newly revitalized Jefferson St. corridor, this bar occupies on old gas station. In the warm months the large bay doors can be opened creating a unique indoor/outdoor space. A large selection of premium beers can be found on tap. 
• 4 McCarthy's Irish Bar, 117 S. Upper St, ☏ +1 859 258-2181. 11AM-2:30AM. Seems to be the default bar for a wide range of people. Sprawled across three storefronts, it has a back patio, no cover charge, and a charismatic old doorman named Miami Steve who usually sports interesting headwear. 
• 5 Molly Brooke's Irish Bar, 109 N Limestone (directly across from the new courthouse), ☏ +1 859 420-5792. An original Irish bar in downtown Lexington. Owned by some Irish people and the staff there are Irish too. The drink prices are good and the crowd is fun. They have a nice old patio outback and sidewalk tables too. 
• 6 The Beer Trappe, 811 Euclid Ave, ☏ +1 859 309-0911, TheBeerTrappe@gmail.com. For beer hobbyists/enthusiasts. Offer hundreds of different beers from different microbreweries. The people who run it also give tasting classes there during some days of the week to teach about different kinds of beer (What's the difference between an IPA and an APA, for example? What does it mean if an IPA says "90-minutes" on it?). You won't find Budweiser here. 
• 7 Tin Roof, 303 S Limestone (at Maxwell St & S Limestone), ☏ +1 859-317-9111, infolexington@tinroofbars.com. Daily 11AM-2:30AM. A cross between a restaurant and bar with an emphasis on live music. Markets itself on a laid back atmosphere. 
• 8 Two Keys Tavern, 333 S. Limestone, ☏ +1 859 254-5000. Quintessential college bar, located straight across the street from UK's north campus and packed with fraternity/sorority students during the school year. The drink selection is limited, but the atmosphere is pleasant. Popular on "Thirsty Thursdays," when the $10 cover gets you all you can drink. 

Around town

• 9 Marikka's Restaurant und Bier Stube, 411 Southland Dr, ☏ +1 859 275-1925. M-Sa 5PM-closing; Su closed. With 30 beers on draught and hundreds more in bottles, this is a place to go for beer lovers. If beer is not your thing, they have an equally-hearty selection of hard liquor, including a dozen bourbons you probably haven't heard of. 
• 10 Survivor's Bar & Grill, 161 E. Reynolds Rd, ☏ +1 859 272-8294. A well known local karaoke bar. This bar is small but attracts a diverse cross section of people looking to show off their skills on the large music selection. 

Nightclubs

If you want to hit the dance floor, there are a few bars that are also nightclubs.

• 11 The Bar Complex, 224 E Main St (next to the Kentucky Theatre), ☏ +1 859 255-1551. The Bar is Lexington's largest and oldest gay club. Their dance floor and show room have an ongoing schedule of DJs and drag shows. 

Sleep

This guide uses the following price ranges for a standard double room:
Budget	Under $80
Mid-range	$80 - $150
Splurge	Over $150

In Lexington, accommodation rooms are taxed at 13.4%. A complete list of hotels, motels and bed and breakfasts can be found at www.visitlex.com

• 1 Kentucky Horse Park Campground, 4089 Iron Works Pkwy (7 miles north of the city), toll-free: +1-888-459-7275. Offers spacious sites with 50/30/20 amp electric and water. All sites are 55' paved back-ins with fire rings and picnic tables. Has many extras including a grocery, gift shop and two bathhouses with modern conveniences. Take advantage of our planned recreational activities or catch a game of tennis or basketball on lighted courts, cool off in the junior olympic–size swimming pool, try your hand at pitching horse shoes, croquet, or maybe square dancing in the recreation pavilion. Also has electric primitive and primitive available for those wishing for a more rustic stay. Planned activities are available on most weekends beginning Memorial Day weekend through Labor Day. Camp has wireless Internet available; first 15 minutes free, various paid time blocks availalble with 24/7 support. $27. 

Budget

• 2 Baymont Inn & Suites, 2400 Buena Vista Rd, ☏ +1 859 293-6113, generalmanager17915@wynhg.com. 
• 3 Bluegrass Extended Stay, 2753 Richmond Rd, ☏ +1 859 269-4999, info@bluegrassextendedstay.com. 
• 4 Days Inn Lexington, 1987 N. Broadway, ☏ +1 859 299-1202. 
• 5 Microtel Inn & Suites by Wyndham, 2240 Buena Vista Rd, ☏ +1 859 447-9514. 
• 6 Motel 6 Lexington East, 2260 Elkhorn Rd (I-75 exit 110), ☏ +1 859 293-1431. 
• 7 GuestHouse Lexington, 2261 Elkhorn Rd (I-75 exit 110), ☏ +1 859 294-7375. 
• 8 Red Roof Inn Lexington South, 2651 Wilhite Dr, ☏ +1 859 277-9400. 

Mid-range

• 9 Clarion Hotel Conference Center - South, 5532 Athens Boonesboro Rd (I-75 exit 104), ☏ +1 859 263-5241, toll-free: +1-800-780-7234. 
• 10 Clarion Hotel, 1950 Newtown Pike (I-75 Exit 115), ☏ +1 859 233-0512. This hotel has a huge atrium with indoor pool and arcade. A restaurant and sports bar are attached. The hotel features a Hertz rental kiosk. 
• 11 Comfort Suites, 3060 Fieldstone Way, ☏ +1 859 296-4446. 
• 12 Hilton Garden Inn, 1973 Plaudit Pl (I-75 exit 108), ☏ +1 859 543-8300. 
• 13 Holiday Inn Express-Downtown/University, 1000 Export St, ☏ +1 859 389-6800, gm.lexky@wm.hiexpress.com. 
• 14 Holiday Inn Express-Lexington Northeast, 1780 Sharkey Way, ☏ +1 859 231-0656. Located just 2 miles from the center of Downtown and 2 miles from Bluegrass Airport, this hotel built in June 2008 is perfect for both business and leisure travelers. 
• 15 Hyatt Place, 2001 Bryant Rd (I-75 exit 108), ☏ +1 859 296-0091. 
• 16 Marriott SpringHill Suites, 863 S. Broadway, ☏ +1 859 225-1500. 
• 17 Ramada Conference Center, 2143 N. Broadway (I-75 exit 113), ☏ +1 859 299-1261, katystephenson@aol.com. 

Splurge

• 18 Gratz Park Inn, 120 West Second St, ☏ +1 859 559-4853. 
• 19 Griffin Gate Marriott Resort & Spa, 1800 Newtown Pike (I-75 exit 115), ☏ +1 859 231-5100. 
• 20 Hilton Lexington Downtown Hotel & Conference Center, 369 West Vine St, ☏ +1 859 231-9000. 
• 21 Hyatt Regency Lexington, 401 West High Street, ☏ +1 859 253-1234, larry.bell@hyatt.com. Integrated into the Convention Center and Rupp Arena. 

Connect

The area code for Lexington and most surrounding counties is 859 (which spells out "UKY", a testament to the popularity of UK basketball). Scott County (including the major suburb of Georgetown), immediately to the north, is in area code 502, but calls between Lexington and Georgetown are local. Outside the metro area, the area code is 606 to the east; 502 serves the state capital of Frankfort. The phone system may be able to correct you if you misuse the area code.

Stay safe

The Lexington Division of Police, accredited by the Commission on Accreditation for Law Enforcement Agencies (CALEA), was awarded "Flagship Status" in 2010 for the third consecutive assessment, becoming the first and only municipal police agency in the U.S. to be so honored. The Police department has several special patrol units, including bicycle, Segway, and a mounted patrol.

Lexington's crime rates rank favorably with other cities of its size.

The University of Kentucky campus is patrolled by the University of Kentucky Police Department and is generally quite safe. An initiative called "Cat's Path" is comprised of a series of recommended walking routes that span central campus. The routes were chosen due to their frequent use and accessibility to the main campus destinations. Marked with highly visible signage and paw print ground logos, the Cat's Path is patrolled frequently by University Police, both on foot and in special police golf carts.

Go next

Lexington's central location makes it the ideal base to explore the Bluegrass Region.

Activities

• An hour east of Lexington, the Red River Gorge, offers numerous opportunities for hiking and rock climbing. Natural Bridge State Park features some of the largest stone arches in the eastern United States. Both are located inside the Daniel Boone National Forest.
• Carter Caves is about an hour and a half east of Lexington near the small town of Olive Hill just outside the Huntington area.
• Kings Island, in Mason north of Cincinnati, is an amusement park just under 2 hours from Lexington, famous for The Beast - the world's longest wooden roller coaster for 30+ years.

Bourbon

Bourbon distilleries are plentiful in the area, due to the particular geology of the region that make this distinctively Kentuckian liquor possible. Many distilleries operate tours where you can learn about the processes of mashing, distilling, and aging, and often sample the product. Five are within 30 miles of Lexington.

• 14 Buffalo Trace, 113 Great Buffalo Trace, Frankfort (~28 miles from downtown), toll-free: +1-800-654-8471. Tours M-Sa year-round; call for times. Free. 
• 15 Four Roses, 1224 Bonds Mill Road, Lawrenceburg (~24 miles from downtown), ☏ +1 502 839-3436. 
• 16 Hartfield & Co., 320 Pleasant Street, Paris, ☏ +1 859 474-0345. Tu-Sa 8AM-10PM. Short tours (10-15 min) Tu-F throughout the day, long tour (1 hr) Sa 6PM by reservation (limit 8 people). The first distillery to operate in Bourbon County, Kentucky, in 95 years, when Prohibition was enacted in Kentucky. Tours free. (updated May 2017)
• 17 Wild Turkey, 1417 Versailles Road, Lawrenceburg (~22 miles from downtown), ☏ +1 502 839-2182. Tours M-Sa 9AM-4PM on the hour; closed some holidays. $11. (updated Jan 2020)
• 18 Woodford Reserve, 7855 McCracken Pike, Versailles (~21 miles from downtown), ☏ +1 859 879-1812. Tours Tu-Sa year-round, Su Apr-Dec. For specific times, call or see web site. Tours $5-10/person; reservations may be required. 

Small bluegrass towns

• Frankfort, Kentucky's capital city, is 25 miles northwest of Lexington on I-64.
• Midway is a quaint and colorful railroad town that's "midway" between Lexington and Frankfort; stop for a bite to eat and explore the antique and boutique shops downtown. It is one of a ring of small bluegrass towns surrounds Lexington at a radius between 12-20 miles from downtown, including Nicholasville, Versailles, Georgetown, Paris and Winchester.
• Richmond, home of Eastern Kentucky University is 26 miles south of Lexington on I-75.
• Bardstown, 60 miles from Lexington, is Kentucky's second oldest city.
• Berea, 37 miles south of the city, is a major center for folk arts & crafts. Old Town has many working artists studios, and the Kentucky Artisan Center, just off I-75, serves as a visitors' center and showcases the wares of many regional artisans.
• Danville, 35 miles southwest of Lexington, is the "City of Firsts", and the "Birthplace of the Bluegrass" since the first Constitutional Convention in the West was held at Constitution Square in 1792 and Kentucky's first Constitution was signed there.
• Harrodsburg, 32 miles southwest of Lexington, is Kentucky's oldest city. Just outside it is Shaker Village of Pleasant Hill, America's largest restored Shaker community, with 34 carefully restored buildings and 3,000 acres of preserved farmland.

Smaller towns and cities in surrounding regions

• Morehead, 65 miles east on I-64. Home to Morehead State University and Cave Run Lake, the largest in eastern Kentucky.
• Huntington, WV, 126 miles east on I-64, on the banks of the Ohio River and firmly within the steep, lush Appalachian Plateau; the second-largest city in West Virginia, home to Marshall University.
• Bowling Green, 161 miles southwest in the Pennyroyal Plateau region, home to Western Kentucky University and nearby Mammoth Cave National Park.
• Pikeville, Prestonsburg and Paintsville are just over 2 hours east.
• Hazard is 115 miles southeast
• Owensboro is 172 miles west, less than a 3 hour drive.
• Charleston, WV is 175 miles east, about a 3 hour drive.

Big cities

• Louisville, 79 miles west, is Kentucky's largest city and is famous for—among other things—the Kentucky Derby and the Louisville Slugger Museum.
• Cincinnati, Ohio, is 82 miles to the north. As Kentucky was a slave state and Ohio was free, this route north was one of the more popular Underground Railroad lines leading to the freedom shores of southwestern Ontario just across Lake Erie.
• Knoxville is 172 miles south, less than a 3 hour drive.
• Indianapolis is 186 miles northwest about 3 hours away.
• Columbus is 190 miles northeast, a little over 3 hours away.
• Nashville is 214 miles southwest, 3 and a half hours away.

Routes through Lexington

Frankfort ← Midway ←	W  E	→ Mount Sterling → Charleston
Cincinnati ← Williamstown ←	N  S	→ Richmond → Knoxville
Cincinnati ← Paris ←	N  S	→ Nicholasville → Chattanooga
Louisville ← Frankfort ← Jct W E ←	W  E	→ Mount Sterling → Charleston
Bowling Green ← Harrodsburg ←	W  E	→ Paris → Wilmington