Ashland is a small town, home of the Oregon Shakespeare Festival, one of the largest and oldest regional theaters in the country. Southern Oregon University balances the tourist population with students throughout the year. The weather is relatively mild, with a few days of snow in the winter, several days of 100F weather in the summer. Some believe that the town resembles northern Italy or Switzerland, with snow-covered peaks in the winter, a lake not too far away in the valley, and a nice, small-town, community feel that is oh-so-rare these days in the States.
There are two main business districts: one downtown, centered on the Plaza and running southwest along Main Street toward the library. This old-fashioned boutique shopping area is home to many amazing restaurants. In fact, you'll have a hard time finding a bad meal. Connected to this area is 93-acre Lithia Park [dead link] which was designed in part by John McLaren (also the designer of San Francisco's Golden Gate Park) in 1914. The other business district is around two miles to the southwest along Siskiyou Boulevard where it meets Ashland Street/Highway 66, near the Southern Oregon University campus and the Ashland Shopping Center. Ashland has a limited number of drive-through permits, and thus fast food joints. Wendy's, Taco Bell, Subway and other chains are still open in Ashland.
Many public places, including most hotels and B&Bs, coffeehouses and even pubs offer free wireless Internet access.
Exit 11 (Northbound only), 14 or 19 from Interstate 5 in Oregon.
Greyhound stops in nearby Medford. The local RVTD bus Route 10 stops at Mr. C's (where the Greyhound bus stations is) at :26 & 56 past the hour. The bus ride into downtown will take you about 10 minutes. Buses run between 5:26AM and 6:56PM, Monday-Friday. You pay when you get on the bus.
Taxi service is available from Ashland Taxi Cab +1 541 890-8080 or Yellow Cab +1 541 482-3065.
The Medford International Airport is located 15 miles north of Ashland and is serviced by Allegiant Air, United Air Lines, and Alaska Airlines/Horizon Air. Cascade Airport Shuttle +1 541 488-1998, taxis and some hotels provides service from the airport to Ashland for a nominal fee.
If you are flying your own plane, you can use the Ashland airport (S03).
The closest Amtrak station is located in Klamath Falls, approximately 80 miles away. A shuttle meets the Coast Starlight from California at 10:20AM each day arriving in Ashland at 1PM If you are traveling from the north you must take the connection bus from Portland to the Ashland shuttle. Both shuttles arrive at Safeway about a half mile from downtown. Check www.amtrak.com for more information. *Note:* The Southwest Point shuttle from Klamath Falls to the area is much cheaper than adding the bus leg on an Amtrak ticket 
Parking is free, and easy to find in the wintertime, but summertime availability is a different story, with downtown parking getting quite scarce on evenings when the Shakespeare Festival has shows (i.e., every night but Monday). Many hotels and B&Bs are located close enough to the center of town to make it an easy walk. There are bike lanes downtown and extending outward from the downtown area, making this an easy town to bike around in.
Most days, the Rogue Valley Transportation District operates buses running from one end of town to the other; these buses are $2.00. Be aware, however, the buses run limited hours (5:30AM to 7PM) and do not run at all on weekends.
Take a walk along Ashland Creek running down from the hills along Lithia Park, along Calle Guanajuato, running behind the Plaza restaurants and storefonts, and through the center of town. There are plenty of picnic benches and sitting benches for contemplation and conversation in the woods, as well as duck ponds, playgrounds, two large greens and a skating rink in the winter.
- 1 Oregon Shakespeare Festival, 15 S. Pioneer St, ☏ , toll-free: (box office). February through November with no plays on Mondays. One of the largest venues for production of Shakespeare's plays in North America, OSF provides a continuous run of theatrical works from early spring until late fall. In a single weekend, adventurous theater lovers can easily fit in 3 or 4 plays. The rotating repertory season of 11 plays typically includes three Shakespeare pieces, with the remainder made up of modern classics, contemporary pieces, and often one or two world or West coast premieres. The staging and acting is of consistently high quality, but the festival is very popular and buying tickets in advance is almost mandatory. Last-minute travelers can pick up spare tickets at the on-site box office or by holding up a sign on the festival plaza (aka "the bricks"). If you come during the spring or fall and/or see shows on Tuesday, Wednesday or Sunday night you can sometimes get Rush tickets from the box office for 50% off or as little as $6. Call the box office the day of and ask if they think any shows will rush. Also $30-50 (discount during spring and fall, 25-50% discount for youth and seniors).
- Ashland Independent Film Festival. Held each year in April.
- Rafting on the Rogue and Upper Klamath Rivers. Check out Indigo Creek Outfitters, Northwest Rafting Company, Kokopelli River Guides, Momentum River Expeditions, Noahs Rafting for 1/2, one day, and multi-day trips.
- 2 Emigrant Lake. A Jackson County park offering boating, lake swimming, fishing, and two large water slides.
- 3 Crater Lake. Is the deepest lake in the US and known for its intensely blue waters. (80 miles north of Ashland).
- 4 Lithia Artisans' Market (Downtown). Seasonal, weather permitting.
- First Friday Artwalk. Is a free event held the first Friday evening of every month in which the galleries and wineries join force. Patrons stroll Ashland's many galleries to meet the artists, see demonstrations and enjoy free refreshments and entertainment.
- Britt Festival. In nearby historic Jacksonville is an open-air concert space with varied events all summer.
- Fishing in the Rogue River.
- 5 Mount Ashland Ski Area, 11 Mt. Ashland Ski Rd, ☏ , email@example.com. On Mt. Ashland.
- Hiking on Mt. Ashland (Pacific Crest Trail proximity).
- Impressive Halloween crowd downtown.
- The Fourth of July Parade is a big event for the town; it draws visitors from around the region.
- Festival of Lights Parade at the end of November; when all the Christmas lights in the town are turned on.
- Oregon Shakespeare Festival. Elizabethan, Angus L. Bowmer and New Theaters.
- Oregon Cabaret. Is the other most compelling theatre in town. Enjoy dinner, drinks and hilarious musical comedy all in the same place. Even if you don't come early for dinner, order a slice of Dick Hay Pie for intermission.
- The Green Show.
- Oregon Stage Works.
- 6 Lithia Park. ’s band shell offers Ashland City Band concerts on Thursday nights and Ballet Rogue performs on Monday nights during the summer.
- 7 Ashland Street Cinema, 1644 Ashland St, ☏ . First-run movies-located in the Ashland Shopping Center at southwest end of town.
- 8 Varsity Theater, 166 E Main St, ☏ . Some smaller run and independent films-located downtown near Ashland Springs Hotel.
- 1 Bloomsbury Books.
Ashland's status as a theater and tourist destination means more good restaurants per capita than might be expected in a town of its size. There are also plenty of budget offerings for the town's college students. Many restaurants offer vegetarian choices. However, Ashland is one of the few places in Oregon that charges a 5% local sales tax on all prepared food. Here are some popular places by price and area:
- 1 Big Al's, 474 N Main St, ☏ . Burgers serves standard and specialty burgers and sandwiches (including veggie burgers) as well as a complete Mexican menu.
- 2 The Breadboard, 744 N Main St, ☏ . Breakfast and lunch.
- 3 Bento's East, 3 Granite St. Asian fusion lunch menu.
- 4 Louie's, 41 N Main St, ☏ , firstname.lastname@example.org. Sometimes has inexpensive lunch specials.
There are also fast food chains like Subway, Taco Bell and Wendy's.
- 6 The Black Sheep, 51 N Main St, ☏ . Tu-Sa 4:30PM-11:30PM, Su 11AM-11:30PM. Remarkably authentic English pub grub.
- 7 Brothers Deli, 95 N Main St, ☏ . Daily 7:30AM-1:30PM. Breakfast and lunch only; omelettes, burgers, and sandwiches.
- 8 Greenleaf Restaurant, 49 N Main St, ☏ , email@example.com. Fresh, Healthy & Delicious. Family Friendly. Breakfast, Lunch, Dinner. Catering, Picnics, Boxed lunches. Vegetarian, Gluten Free & Vegan options. Hot sandwiches, soups, salads and specialties. Creekside dining.A local favorite for over 25 years.
- Louie's, 41 N Main St. Voted "Most Interesting Burgers" and "Best Value on the Plaza" by Ashland's Sneak Preview Magazine. A fun and family-friendly "Cheers" atmosphere. Creekside dining.
- 9 Pangea, 272 E Main St, ☏ . Wraps, sandwiches, salads and soups. (well-behaved dogs OK at sidewalk tables.)
- 10 Morning Glory, 1149 Siskiyou Blvd (Right next door to Subway), ☏ . Wonderful breakfasts and lunches.
- 11 Omar's, 1380 Siskiyou Blvd, ☏ , firstname.lastname@example.org. 4PM-9PM. Traditional dining, steaks & seafood.
- 12 Larks, 212 E Main St. American gourmet, including comfort foods. (well-behaved dogs OK at sidewalk tables.)
- 13 Thai Pepper, 84 N Main St, ☏ . W-Su 5PM-9PM. Thai cuisine. Creekside dining.
- 14 The Winchester Inn, 35 S 2nd St, ☏ . New American cuisine with French influence. Outside garden patio seating. Wine Spectator Award of Excellence. Great wine bar.
- 1 Creekside Pizza, 92 1/2 N Main St, ☏ . Newly reopened with a satisfying selection of beer and pizza.
- The Black Sheep, 51 N Main St, ☏ . Tu-Sa 4PM-11:30PM, Su 11AM-11:30PM. English-style pub offering a full menu of many pub food classics and specialties as well as draft and bottled beers and spirits.
- Louie's Bar and Grill, 41 N Main St. Family-friendly "Cheers" atmosphere, bi-weekly rotating microbrews, historic 100-year-old restored bar.
- 2 The Caldera Taproom, 590 Clover Ln, ☏ . Extensive offering of beer brewed in Ashland by Caldera Brewing Company with a small menu of pub fare.
- 3 Winchester Wine Bar, 35 S 2nd St. Specializes in local wines. They have wineries pour every Thursday night. The bar also functions as a retail bottle shop. Live music on Fridays and Saturdays with no cover.
- 4 Grizzly Peak Winery, 1600 E Nevada St, ☏ , email@example.com.
- 5 Noble Coffee Roasting, 281 4th St, ☏ . Locally (small-batch) roasted organic and fair trade coffee and a sleek, laid-back space. Located in the railroad district near several art galleries and the Greenway walking/biking path. Free wireless.
- 6 Mix Bakeshop, 57 N Main St, ☏ , firstname.lastname@example.org. Su-Th 7AM-9PM, F-Sa 7AM-9:30PM. Serves Stumptown Coffee (from Portland a leading direct trade coffee roaster). Right downtown on the plaza high-quality sweets, pastries, and coffee. Homemade ice cream. Free wireless.
- 7 Case Coffee, 44 Lithia Way. Located directly across from the SOU campus on Siskiyou Blvd. Free wireless.
- 8 The Beanery. Ashland and Walker Streets, at the Southwest end. Free wireless.
- 9 Rogue Valley Roasting Company, 917 East Main St, ☏ . M-Sa 6:45AM-6PM, Su 7AM-3PM. Serving great coffee, fantastic locally-made pastries (both sweet and savory!) and ice cream, along with many other great hot and cold drinks. Free wireless, In-House Computer, as well as Outdoor porch or patio seating.
- 10 La Baguette/Hardware Cafe, 340 A St (at Third), ☏ . Mostly a bakery, has excellent stuffed bagels, breads and other baked treats. Not open on the weekend.
- Bloomsbury Books. Has a coffeehouse in its second-floor loft. Free wireless.
- 1 Winchester Inn, 35 S 2nd St, ☏ , toll-free: . Two blocks from OSF. 19 rooms and suites. Full gourmet breakfast included. Beautiful gardens. Free WiFi. Great packages available. Historic building, 1st southern Oregon Hospital. Rates are $140-190 in winter, $165-299 in spring/fall and $205-299 in summer.
- 2 Palm Cottages, toll-free: . Across from Southern Oregon University, a few blocks from downtown, and is known for being a two-time winner of the Ashland Garden of Month award. It has a pool, a lot of gardens, phones, cable TV, kitchens, free WiFi and a horde of other amenities. Rates range from $64 to $98 in winter, $69-$115 in Spring/Fall and $95-169 in summer.
- 3 Columbia Hotel, toll-free: . Right downtown 1 block from the Oregon Shakespeare Festival at 262 East Main Street. Rates range from $49 to $69 in winter, $59-$105 in Spring/Fall and $73-$125 in summer. The Columbia is special in that walking up the stairs is akin to going back to 1910 when it was built. It's a must see when you visit Ashland.
- Ashland's Bed and Breakfast Network, toll-free: . Is an association of 25+ inns that cooperatively provide free lodging referral service for visitors to Ashland, Oregon. ABBN is Ashland's only lodging association run entirely by volunteers, and the B&B have all met the associations high standards set for membership.
- 4 Chanticleer Inn, 120 Gresham St, ☏ . Ashland's oldest luxury B&B in quiet historic neighborhood. Elegantly renovated 1920 Craftsman. Gourmet breakfasts, organic coffee, cookies, pvt baths, king beds, AC, WiFi, NYTimes, secluded gardens.
- 5 Arden Forest Inn, 261 W Hersey St. Bed & breakfast on an acre of lush, park-like gardens.
- 6 Ashland Springs Hotel, 212 E Main St, ☏ . Downtown on East Main Street in a historic building which was, for many years, the tallest building between San Francisco and Portland.
- 7 The Plaza Inn, 98 Central Ave, ☏ , toll-free: . Generic hotel located north of downtown.
- Mt Ashland House. The only year round vacation rental actually on Mt. Ashland, on the access road (Mt. Ashland Ski Rd) is a 2 bedroom, split level log home, minutes from skiing (Mt. Ashland Ski resort), hiking (The Pacific Crest trail), biking and the Beautiful Tashi Chöling’s traditional Tibetan temple, makes this the perfect vacation rental. Mt. Ashland House is on a acre of land, in a private, secluded location. Mt. Ashland House is just 6 miles north of the California border, at the 5,000 foot level.
- 8 Ashland Commons, 437 Williamson Way (see website), ☏ . Check-in: 4PM, check-out: 10:30AM. Two homey units; perfect for groups, families, as well as individuals. 2 equipped kitchens, 6 bedrooms, 4 baths, a/c, tv, wifi, off street parking, laundry, patio. Walk to downtown and theaters. $20-$45.
- High Street Cottage. Lovely little two-bedroom house within walking distance of downtown shops, theaters and park. Immaculately clean and well-kept by the owners.
- 9 Ashland Mountain House B&B, 1148 Old Hwy 99 S (4 miles south of town), toll-free: . Check-in: 4-7PM, check-out: Noon. Built in 1852, the Ashland Mountain House served as a stagecoach stop for 25 years. Today, this old yellow farmhouse 5 miles from town is once again welcoming weary travelers with its gracious hospitality and beautiful setting on 6 acres overlooking hills and valleys. Inside the inn, you'll find a library with an antique Steinway piano and floor-to-ceiling shelves of books. Wood floors and original woodwork give the interior a classic feel, while hand-silk-screened wallpapers do a great job of conjuring up this old house's early years. $139-$209.
- 10 Country Willows Inn, 1313 Clay St, ☏ . A country bed and breakfast with eight rooms and suites, one private cottage, an onsite pool and nearby hiking trails. $160-310.
- 11 Ashland Hills Hotel and Suites, 2525 Ashland St, toll-free: .
|Routes through Ashland|
|Medford ← Talent ←||N S||→ Hornbrook → Redding|
|END ←||W E||→ Klamath Falls → END|