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 $1.40 for 1-2 towns on a CharlieCard/$1.75 cash, and $3.60 for 3+ towns on a CharlieCard/$4.50 cash. Unlimited 1-day, 7-day, and 30-day passes are also available. Seniors are half-fare. The buses are generally clean and quiet, and only heavily occupied during rush hour times.
Rainbow Taxi is the sole taxicab provider for the area, and can be reached at +1 413-499-4300. 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.
Hancock Shaker Village, Routes 20 and 41, Phone: +1 413 443-0188, toll free +1 800 817-1137, . 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. See other Shaker villages in the northeast United States through the itinerary Touring Shaker country.
Albany Berkshire Ballet, 51 North Street, Phone: +1 413 445-5382. Professional ballet company, performs classical and contemporary dance.
Artscape, A self-guided tour of artwork in downtown Pittsfield.
Arrowhead, Home of Herman Melville, 780 Holmes Road, Phone: +1 413 442-1793, . Melville's home from 1850 to 1862, where Moby Dick and other works were written. House tours, gardens, nature trail, exhibits, museum shop.
Berkshire Artisans, 28 Renne Avenue, Phone: +1 413 499-9348. Municipal arts center.
Berkshire Athenaeum, 1 Wendell Avenue, Phone: +1 413 499-9486, . History and genealogy.
Berkshire Lyric Theatre, 413-499-0258, . Chorus performs at various locations.
Berkshire Museum, Route 7 Downtown, Phone: +1 413 443-7171. The region's only museum of art, science and history.
Berkshire Music Hall, 58 Union Street, Phone: +1 413 499-5575. A 1912 vintage theatre presenting local and national productions from music to drama.
Berkshire Opera Company, 297 North Street, Phone: +1 413 442-9955, . Performs at Koussevitzky Arts Center, Berkshire Community College
Pittsfield Suns, plays at 105 Wahconah St., Phone: +1 413 447-3853. New England Collegiate Baseball Team plays at historic Wahconah Park.
Silvio O. Conte National Records Center, 100 Dan Fox Dr., Phone: +1 413 445-6885. M-F 9AM-3PM. Primarily of interest to genealogists.
South Mountain Concerts, Routes 7 & 20, Phone: +1 413 442-2106. Su afternoons during Sep & Oct. Chamber music since 1918.
Town Players, Performs at Berkshire Community College, Phone: +1 413 443-9279. October - May. America's oldest community theater.
The Pittsfield Fourth of July Parade, South Street to Wahconah Park via North Street, ☎ (413) 447-7763, . 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. edit
Absolutely Experiential, Phone: +1 413 443-8383, email@example.com, . High Ropes Course, Climbing Tower and Zip Line. Kayaking and other guided Berkshire adventures.
Berkshire Sculling Association, Brubank Park, Onota Lake, +1 413 496-9160, firstname.lastname@example.org, . Instruction and rentals are available appointment only.
Bousquet Ski Area/Play Bousquet, 101 Dan Fox Drive, Phone: +1 413 442-8316, . 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.
Onota Boat Livery, 463 Pecks Road, Phone: +1 413 442-1724.  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!
U-Drive Boat Rentals, 1651 North Street, Phone: +1 413 442-7020. Boat rentals on Pontoosuc Lake.
Wild N Wet Snow & Water and Bike Rentals, Route 7, Pontoosuc Lake, Phone: +1 413 413-445-5211.
3rd Thursdays, Downtown Pittsfield, ☎ (413) 499-9348. 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.edit
Berkshire Mall, Old State Road & Route 8, Lanesborough, MA 01237, ☎ (413) 445-4400, . Mon-Sat 10am - 9pm, Sun 11am - 6pm. One of the main shopping centers of the region, though it's small, with only one story. It contains mostly the "big box" stores you'd expect: Target, Best Buy, Sears, JCPenney, etc., though there are also some specialty shops and a small arcade. It also has a 12-screen Regal Cinema location.edit
Allendale Shopping Center, 5 Cheshire Road, ☎ (413) 236-5956. edit
Berkshire Crossing, 555 Hubbard Avenue, ☎ (617) 406-2650. The other main shopping center 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.edit
Jimmy's Restaurant, 114 West Housatonic Street, Phone: +1 413 499-1288. Italian
Knee Bones Steakhouse, Allendale Shopping Centre, Phone: +1 413 442-9537.
Dottie's Coffee Lounge, 444 North St., Phone: +1 413 443-1792.
Digital Blend, 76 North St., Phone: +1 413 445-9991. Coffee drinks, wraps, beer, wine.
Kelly's Diner, 860 Dalton Ave., Phone: +1 413 442-1875. Breakfast, lunch, best sausage in town.
One West, One West Street, Pittsfield MA, ☎ (413) 499-2000, . edit
The Underground, One West Street, ☎ (413) 499-2000, . Mon-Sat 4 pm - 12 am Sun 12 pm - 12 am. Located inside the Crowne Plaza. Entertainment nightly. Kitchen open Mon - Sat 4 pm - 10 pm, Sunday 12 pm - 10 pmedit
Juice & Java, 2 South Street, ☎ (413) 236-8200, . Mon-Fri 7AM-6PM, Sat 7AM-3PM. Free Wi-Fi.edit
Daddyo's Diner, 511 East Street, ☎ (413) 499-1180. Mon 6:30AM-3PM, Tue-Sat 6:30AM-7PM, Sun 6:30AM-2PM. edit
Teddy’s Pizza & Family Restaurant, 508 East Street, ☎ (413) 443-9030, . Family-owned and run pizza house & bar.edit
One West, One West Street, Pittsfield MA, ☎ (413) 499-2000, . Restaurant located inside Crowne Plazaedit
The Underground, One West Street, Pittsfield, ☎ (413) 499-2000, . Mon-Sat 4 pm - 12 pm, Sun 12 am - 12 am. Located inside the Crowne Plaza. Entertainment nightly. Kitchen open Mon - Sat 4 pm - 10 pm, Sunday 12 pm - 10 pmedit
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.
Of more 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, picnicing, 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.
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