- Albany International Airport (ALB IATA), Albany, New York. (About 45 mi (72 km) away)
- Bradley International Airport (BDL IATA), Windsor Locks, Connecticut. (About 75 mi (121 km) away)
Pittsfield is on Routes 20 and 7, accessible via Interstate 90 (Massachusetts Turnpike) Exit 2.
Pittsfield is a rail stop on Amtrak Lakeshore Limited service, which operates daily between Boston and Chicago. Trains stop at the 1 Joseph Scelsi Intermodal Transportation Center, which also serves as a hub for local buses.
Pittsfield is served by several intercity bus lines offering regular service to Boston, New York, Albany, Hartford and points in between.
- The Pittsfield Visitors Center, 111 South Street (Route 7) in the lobby of the newly renovated Colonial Theatre downtown, +1 413 443-9186, x232 or x324.
- The Joseph Scelsi Intermodal Transportation Center, 1 Columbus Avenue, the hub for the Berkshire Regional Transit Authority.  The BRTA offers service stretching from North Adams above Pittsfield, down to Great Barrington below it. Service runs roughly from 6AM to 7PM, with trips usually running once an hour, though it can vary by route. There is no service on Sundays. Fares are $1.25 per city traveled, with half-fare for seniors, and discounted to $1.05 if you buy a 20-fare passcard. The buses are generally clean and quiet, and only heavily occupied during rush hour times.
- Rainbow Taxi can be reached at +1 413 499-4300.
- Arrow Taxi can be reached at +1 413 499-8604
You will need to call a taxi in order to be picked up, instead of flagging one. Be warned that during inclement weather or rush hour the wait for a taxi to arrive can easily be a half-hour or longer.
- Walking is also an option, as the city is fairly small and safe. Many parts of the city are reachable with an hour or less of walking, especially if you're staying at the Crowne Plaza.
Note that if you have a library card from one of the libraries in the C/W MARS network, or know someone who is willing to use theirs for you, you can get free or reduced cost passes  to several of the museums and historical homes/sites listed here.
- 1 Albany Berkshire Ballet, 51 North Street, ☏ . Professional ballet company, performs classical and contemporary dance.
- Artscape, a self-guided tour of artwork in downtown Pittsfield.
- 2 Arrowhead, Home of Herman Melville, 780 Holmes Road, ☏ . Melville's home from 1850 to 1862, where Moby Dick and other works were written. House tours, gardens, nature trail, exhibits, museum shop.
- 3 Berkshire Artisans, 28 Renne Avenue, ☏ . Municipal arts center.
- 4 Berkshire Athenaeum, 1 Wendell Avenue (Some parking available on Wendell Ave, main parking lot is at the lower level on Bartlett Ave), ☏ . History and genealogy. Free or reduced passes to many attractions are available if you have a library card.
- Berkshire Lyric Theatre, ☏ . Chorus performs at various locations.
- 5 Berkshire Museum, 39 South St (Route 7 Downtown.), ☏ . The region's only museum of art, science and history.
- 6 Berkshire Music Hall, 58 Union Street, ☏ . A 1912 vintage theatre presenting local and national productions from music to drama.
- 7 Berkshire Opera Company, 297 North Street, ☏ . Performs at Koussevitzky Arts Center, Berkshire Community College
- 8 Colonial Theatre, 111 South Street, ☏ . A historic theatre with an ornate, turn-of-the-20th century interior. Declared a National Historic Treasure, it was restored in 2006. Weekly theatrical and musical performances.
- 9 Hancock Shaker Village, 1843 West Housatonic Street (On Routes 20 and 41. The entrance is 1/2 mile from the Pittsfield border in Hancock, at 34 Lebanon Mountain Rd.), ☏ , toll-free: . A widely acclaimed destination named The City of Peace by its residents, this Shaker community disbanded in 1960 and sold the buildings and over 900 acres to a group that formed a nonprofit preservation organization. This Shaker site is in remarkable shape, and features a unique round stone barn. It now encompasses about 1,200 acres and 20 restored buildings. While the Village is based in Hancock, and that town gives the Village its name, a substantial part of the Village is in Pittsfield. See other Shaker villages in the northeast United States through the itinerary Touring Shaker country.
- 10 Pittsfield Dukes, 105 Wahconah St, ☏ . Plays at 105 Wahconah St. New England Collegiate Baseball Team plays at historic Wahconah Park.
- 11 Silvio O. Conte National Records Center, 100 Dan Fox Dr, ☏ . M-F 9AM-3PM. Primarily of interest to genealogists.
- 12 South Mountain Concerts, 730 South Street (Routes 7 & 20), ☏ . Su afternoons during Sep & Oct.. Chamber music since 1918.
- Town Players, ☏ . Performs at Berkshire Community College. October - May. America's oldest community theater.
- The Pittsfield Fourth of July Parade, South Street to Wahconah Park via North Street, ☏ . 10AM to 12PM. Named by USA Today as "one of the best parade venues in the country", it has floats, bands, balloons, and processions from all over Berkshire County, and attracts thousands of attendees to the normally quiet city (a notable sight in and of itself). If the 4th falls on a Sunday, the parade will be held on the 5th instead. free.
- Absolutely Experiential, ☏ , ✉ firstname.lastname@example.org. High Ropes Course, Climbing Tower and Zip Line. Kayaking and other guided Berkshire adventures.
- [formerly dead link] Berkshire Sculling Association, ☏ , ✉ email@example.com. Brubank Park, Onota Lake. Instruction and rentals are available appointment only.
- 1 Bousquet Ski Area/Play Bousquet, 101 Dan Fox Drive, ☏ . 21 trails, 98% snowmaking. Day and night family oriented ski school. Rental skis and snowboards. In the summer water slides and other activities are available at Play Bousquet.
- 2 Canoe Meadows Wildlife Sanctuary (Mass Audobon Society), Holmes Rd., ☏ , ✉ firstname.lastname@example.org. Trails, observation building, guided activities. Managed by Pleasant Valley Wildlife Sanctuary
- 3 Onota Boat Livery, 463 Pecks Road, ☏ . Hourly, half-day, and full-day boat rentals on Onota Lake, including row boats, canoes, kayaks, pedal boats, fishing boats and pontoon boats. Fully stocked tackle and live bait shop, including MA fishing licenses and an awesome selection of ice-fishing gear. Open daily, year-round. Visit our website for current rental rates and directions!
- 4 U-Drive Boat Rentals, 1651 North Street, ☏ . Boat rentals on Pontoosuc Lake.
- 5 Wild N Wet Snow & Water and Bike Rentals, 1402 North Street, ☏ . Route 7, Pontoosuc Lake.
- 3rd Thursdays, Downtown Pittsfield, ☏ . Each 3rd Thursday from May to October. A recurring town festival in which art displays, concerts, various activities, and sidewalk booths are held/shown one day of each month in the summer/fall in the Downtown area around North Street and Park Square. Many downtown businesses will also offer special discounts to customers on the festival days even if they don't feature booths or activities.
- 6 U-Drive Rent-A-Boat, 1651 North Street (On Rt. 7, on the Lanesborough-Pittsfield border, right next to the Donut Man), ☏ . Rentals for pontoon boats, canoes and kayaks. Up to 14 people can enjoy a Pontoon Boat.
- first come - first serve
- Herberg Middle School, 501 Pomeroy Avenue.
- Lakewood Park, Newell Street.
- Pittsfield High School, 300 East Street.
- Ponterril Tennis Courts, East Acres Road.
- Taconic High School, 96 Valentine Road.
Public golf courses
- 7 General Electric Athletic Club, 303 Crane Ave, ☏ .
- 8 Pontoosuc Lake Country Club, 38 Kirkwood Dr, ☏ .
Biking and Hiking
- Pittsfield State Forest, Cascade Street, ☏ . Trails, biking, birding, swimming (no lifeguards), non-motorized boating.
- 1 Allendale Shopping Center, 5 Cheshire Road, ☏ .
- 2 Berkshire Crossing, 555 Hubbard Avenue, ☏ . One of the main shopping centers in the region. Has Walmart, Home Depot, Barnes & Noble, and Staples as its main stores. Note that the parking lot is rather byzantine and can be annoying to navigate in if you're not familiar with it.
- 3 Stop and Shop Plaza (TJ Maxx Plaza), 660 Merrill Rd (Off of Rt. 9.). This plaza includes Stop and Shop, TJ Maxx, Radio Shack, Dollar Tree, and others. Note that the plaza is divided into two sections, the southern section with Stop and Shop as the main store, the northern part with TJ Maxx.
- 4 Dalton Avenue Plaza Shopping Center, 457 Dalton Av (On Dalton Ave). Price Rite, Jo Ann Fabrics, and other stores. Also has the restaurant China Wok.
- 5 Bed Bath & Beyond, 665 Merrill Road (On Merrill Rd, part of The Shops at Unkamet Brook complex), ☏ . M-Sat: 9:00am - 9:00pm Sun: 10:00am - 6:00pm. National chain, offers a wide variety of home goods
- 6 Dick's Sporting Goods, 635 Merrill Rd (On Merrill Rd, part of The Shops at Unkamet Brook complex). M:9:00am - 7:00pm T-Sat: 9:00am - 9:30pm Sun: 10:00am - 7:00pm. National sporting goods chain
- See also the Berkshire Mall in Lanesborough off Rt. 8. If you're travelling via the BRTA, note that this counts as a two-city trip even though the mall is literally just over the Lanesborough border. If you want to save a couple bucks, it is allowed to get off before the border (or even back at Allendale) and walk, though beware that there will be no sidewalk and no crosswalks.
- 1 Knee Bones Steakhouse, ☏ . Allendale Shopping Centre.
- 2 Kelly's Diner, 860 Dalton Ave, ☏ . Breakfast, lunch, best sausage in town.
- 3 One West, One West Street, Pittsfield MA, ☏ . Located at the Crowne Plaza
- 4 The Underground, One West Street (inside the Crowne Plaza), ☏ . Mon-Sat 4 pm - 12 am Sun 12 pm - 12 am. Entertainment nightly.
- 5 [dead link] Patrick's Pub, 26 Bank Row (In downtown Pittsfield, on the junction of South and East St at the park circle), ☏ . Sun-Th: 4:30 pm - 10:30 pm; F and Sat: 4:30 pm - 11:30 pm. Bar and grill, generally well reviewed. May be busy with slow service at times, but good food.
- 6 Juice & Java, 2 South Street, ☏ . Mon-Fri 7AM-6PM, Sat 7AM-3PM. Free Wi-Fi.
- 7 Daddyo's Diner, 511 East Street, ☏ . Mon 6:30AM-3PM, Tue-Sat 6:30AM-7PM, Sun 6:30AM-2PM.
- 8 Teddy’s Pizza & Family Restaurant, 508 East Street, ☏ . Family-owned and run pizza house & bar.
- 9 Dottie's Coffee Lounge, 444 North St, ☏ .
- 10 Digital Blend, 76 North St, ☏ . Coffee drinks, wraps, beer, wine.
- 11 The Lantern (Lantern Bar and Grill), 455 North Street, ☏ , ✉ email@example.com. Bar and burgers $11-$30.
- 12 Wheeler's Market, 1654 North Street (On Rt. 7, at the Lanesborough-Pittsfield border.), ☏ . Monday-Friday 6:30am-9pm, Saturday 8am-9pm, Sunday 8am-8pm. Deli and convenience store, includes beer and wine. Across from Pontoosuc Lake.
- 13 99 Restaurant and Pub, 699 Merrill Road, ☏ . 11:00am-10:30pm (bar closes at 11pm) Mon-Thur, 11am-11pm (bar closes 11:30pm) Fri-Sat, 11-10pm Sun. Family-friendly bar & grill
- 14 Jimmy's Restaurant, 114 West Housatonic Street, ☏ . Italian
- 15 The Roasted Garlic, 483 West Housatonic St (On W Housatonic St.), ☏ , ✉ firstname.lastname@example.org. Mon-Thurs: 11:30-9pm Fri-Sat: 11:30am-10pm Sunday: noon-8pm. Wood-fired pizza, bar & grill. Highly reviewed, pleasant atmosphere. $11-$30.
- 16 Flo's Diner, 1245 W Housatonic St (On Rt. 20), ☏ . 7am-2:30pm Mon-Sat; 7am-1:30pm. Breakfast and lunch. Expect a long wait.
- 17 Port Smitt's Lakeway Restauran, 370 Pecks Rd, ☏ , fax: . M 4pm-12am Tu-Sun. 11:30am-12am. Highly reviewed, good food. Can be very busy, so it is best to make reservations on weekends. Might not always be the best atmosphere for young children.
- 1 Methusela Bar and Lounge, 391 North St, ☏ , ✉ email@example.com. 5pm-1am; closed Sunday. Wine bar with a rustic/chic theme $11-$30.
- 2 Mission Bar & Tapas, 438 North Street, ✉ firstname.lastname@example.org. 5pm-12am; Friday and Saturday 12pm-12am; closed on Sunday. Tapas bar with Spanish small plates, Iberian wines and music. $11-$30.
- 3 Tavern at the A, 303 Crane Ave, ☏ , ✉ TavernAtTheA@gmail.com. Tue-Thu 11:30am-8:00pm, Fri and Sat 11:30am-1:00am. Full pub menu and bar. Catering and special event bookings are available. Weekends come alive with musical entertainment. The grounds feature an 18 hole golf course.
- 1 Heart of the Berkshires Motel, 970 W Housatonic St (On Rt. 20), toll-free: . Located along Rt. 20. No-frills motel; free wi-fi. Reviews are mixed. $70 and up.
Hotels and motels
- 2 Crowne Plaza Hotel, One West Street (Route 7 & West St. 1 West Street.), ☏ , toll-free: , ✉ email@example.com. One of the tallest buildings in Pittsfield
- 3 Best Western - Berkshire Hills Inn & Suites, 1350 West Housatonic Street.
- 4 Pittsfield State Forest, 1041 Cascade Street, ☏ . Mid-May to Mid-Oct. 31 campsites.
- 5 Bonnie Brae Cabins & Campsites, 108 Broadway Street, ☏ , ✉ firstname.lastname@example.org. 48 sites.
Pittsfield is for the most part a sleepy city with a low crime rate, and usually safe to walk through even after dark, but you may want to exercise some caution while on the side of the city west of North Street late at night, or when in the neighborhoods along and off of Linden, Lincoln, and Tyler St. and Dewey and Madison Av.
Also of concern is the PCB contamination caused by General Electric's toxic waste dumping during the middle decades of the 1900s. While much of it has since been cleaned up, there are still a few areas that are not safe for human activity. One main one is the Housatonic River, which is still dirty and contaminated; do not fish, swim, wade, etc. in the river waters or any ponds or flood plains that spring from it. The other main one is Silver Lake. While it looks cleaner and is worth driving past because the area is scenic and has many geese and ducks, it too is not safe for swimming, wading, picnicking, etc. There are a few other areas still contaminated as well, mainly around the river; basically, if you see a sign saying the area is contaminated or has PCBs, heed it. Onota and Pontoosuc offer plenty of safe water to frolic in, and there's no shortage of pretty places to walk in Pittsfield, so you won't be missing much.
|Routes through Pittsfield|
|Buffalo (Depew) ← Albany (Rensselaer) ←||W E||→ Springfield → Boston|
|Rutland ← Lanesborough ←||N S||→ Lenox → Danbury|
|Albany ← Rensselaer ←||W E||→ Lenox → Springfield|
|North Adams ← Lanesborough ←||N S||→ Becket → Torrington|
|END ←||W E||→ Northampton → Worcester|