Pittsfield

Travel Guide
Pittsfield featuring a city
Located at a fork in the Housatonic River, this city provides an appealing mix of cultural diversions and outdoor pursuits.

The largest town in the Berkshires region, Pittsfield has varied shops, services and restaurants, making it a great jumping-off point for hiking and camping trips to the nearby Pittsfield State Forest. There is much to explore within Pittsfield itself. Check out colorful street art, discover museum exhibits and attend performances in one of its cultural venues.

Pittsfield was settled in the mid-18th century after a wealthy Bostonian purchased the land as a speculative investment. The village slowly grew in size during the 1800s and 1900s as wool and electrical manufacturing industries flourished. Get a taste of local history at the Berkshire Museum, one of the main tourist draws. A small museum with eclectic exhibits focusing on art, history and nature, it also has an interactive aquarium and hands-on activities for kids to enjoy.

In downtown Pittsfield, enjoy Artscape, a self-guided walking tour of the city’s street art. Take a guided tour of Herman Melville's Arrowhead, the lovingly maintained former residence ofHerman Melville, who wrote his famous novel Moby Dick here in Pittsfield.

In the evenings enjoy culture with a classical or contemporary professional ballet performance at the Albany Berkshire Ballet. Investigate the Colonial Theater, a gilded old theater that has been fully restored and offers an entertaining program including music and theatrical performances. The Pittsfield Visitors Center is found in the theater’s lobby.

In summer, make a splash at the area’s numerous lakes, which have plentiful opportunities for swimming, fishing and boating. As well as hiking through the forest, find year-round recreation available at the Bousquet Ski Resort and Family Fun Center. Stop at the complex outside of ski season to enjoy the water park and go-karting track, perfect for summer fun.

Drive to Pittsfield or use Amtrak's Lakeshore Limited rail service, which operates daily between Boston and Chicago. Pittsfield is also served by intercity bus lines from Boston, New York and Albany.

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is €100 per night from 30 Nov to 1 Dec
€100
includes taxes & fees
30 Nov - 1 Dec
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (677 reviews)
"The front desk staff went above and beyond to make sure that our stay went off without a hitch. Thank you kindly.!"

Reviewed on 10 Nov 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites
2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
The price is €103 per night from 1 Dec to 2 Dec
€103
includes taxes & fees
1 Dec - 2 Dec
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,000 reviews)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"

Reviewed on 11 Nov 2024

Best Western Plus Berkshire Hills Inn & Suites
Hotel On North
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
The price is €154 per night from 19 Nov to 20 Nov
€154
includes taxes & fees
19 Nov - 20 Nov
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (647 reviews)
Gorgeous, elegant history
"Fantastic hotel! Beautiful restored building with loving attentive staff. I was pleasantly surprised by this stay and would highly recommend a stay here. Hope to return one day."

Reviewed on 11 Nov 2024

Hotel On North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
Pittsfield
Stay at this vacation home in Pittsfield. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Tanglewood Music Center and Bousquet Ski Area ...
8.6/10 Excellent! (7 reviews)
Excellent house
"Great view from the property, lovely house and yard. Coiuldn't have been a better stay."

Reviewed on 29 Sep 2024

Chic Pittsfield Home With A View!
Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
Hancock
Stay at this vacation home in Pittsfield. Enjoy a pool table, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Jiminy Peak Mountain Resort ...
9.8/10 Exceptional! (7 reviews)
Great place
"Very kinda hosts, and wonderful house."

Reviewed on 22 Oct 2024

Hancock Village Inn at Jiminy Peak
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our ...
8.6/10 Excellent! (1,744 reviews)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."

Reviewed on 12 Nov 2024

Vacation Village in the Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Reviews of Pittsfield

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Top destination
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4/5 - Good

Verified traveller

Visited Soda Chef for breakfast - recommend the pancakes and the owners are very welcoming