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 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 AU$181 per night from 16 May to 17 May
AU$181
per night
16 May - 17 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 ...
7.8/10 Good! (573 reviews)
"Lovely indoor pool. Very helpful staff. View of the Berkshires from my window."

Reviewed on 14 Apr. 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 AU$182 per night from 8 May to 9 May
AU$182
per night
8 May - 9 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 ...
8.4/10 Very Good! (936 reviews)
"The staff are awesome!"

Reviewed on 30 Apr. 2024

Best Western Plus Berkshire Hills Inn & Suites
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is AU$281 per night from 9 May to 10 May
AU$281
per night
9 May - 10 May
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the clean rooms in our reviews. Popular ...
8.8/10 Excellent! (308 reviews)
"Nice and clean, staff were excellent"

Reviewed on 28 Apr. 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 our ...
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
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
Pittsfield
Stay at this vacation home in Pittsfield. Enjoy WiFi, onsite parking, and a garden. Popular attractions Tanglewood Music Center and Bousquet Ski Area are located ...
9/10 Wonderful! (4 reviews)
Great getaway house
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."

Reviewed on 10 Oct. 2023

Chic Pittsfield Home With A View!
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 children's pool, and a health club. Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,670 reviews)
"Very nice spot quiet"

Reviewed on 24 Apr. 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.

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