Pittsfield Travel Guide

Tourist Guide
Pittsfield showing heritage elements and flowers
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 colourful 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 of Herman 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 Theatre, a gilded old theatre that has been fully restored and offers an entertaining programme including music and theatrical performances. The Pittsfield Visitors Centre is found in the theatre’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 Centre. 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.

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 ฿4,050 per night from 20 May to 21 May
฿4,050
per night
20 May - 21 May
Stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi and free parking. Our guests praise the breakfast and the helpful staff in ...
8.4/10 Very Good! (938 reviews)
"Staff was wonderful. Hotel is very clean. Beds are very comfortable.The free breakfast includes plenty of choices. Coffee, tea and hot chocolate is available all day in the lobby-such a nice touch!"

Reviewed on 4 May 2024

Best Western Plus Berkshire Hills Inn & Suites
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
The price is ฿4,174 per night from 11 May to 12 May
฿4,174
per night
11 May - 12 May
Stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking and breakfast. Our guests praise the helpful staff and the clean rooms in their ...
7.8/10 Good! (576 reviews)
Trip to Pittsfirld
"Staff, friendly and accommodating"

Reviewed on 6 May 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is ฿6,064 per night from 17 May to 18 May
฿6,064
per night
17 May - 18 May
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking and a fitness centre. Our guests praise the clean rooms in their reviews. Popular ...
8.8/10 Excellent! (310 reviews)
"A good stay. Clean and quite. Nice pool and fun for the Kidspiration"

Reviewed on 5 May 2024

Berkshire Mountain Lodge
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.
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in their ...
8/10 Very Good! (856 reviews)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"

Reviewed on 19 Nov 2023

Jiminy Peak Mountain Resort
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
1 Oct 2019

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

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