Pittsfield

Travel 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 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 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 P5,485 per night from 29 May to 30 May
P5,485
per night
29 May - 30 May
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (578 reviews)
"You walk in and you’re greeted with a smile, you’re treated respectfully and everyone is so very helpful! Second time I’ve stayed here in a year and it is the only place I’m going to book when I’m in the area."

Reviewed on May 10, 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 P6,318 per night from 27 May to 28 May
P6,318
per night
27 May - 28 May
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (943 reviews)
"The hotel was farther off of the freeway than I thought it would be. But it was a nice quiet room with a good breakfast. The workout room had a decent treadmill. The stepper needed a battery and the Peloton needed help from the employee to connect to the internet so we didn't ask. The staff was super ..."

Reviewed on May 14, 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 P9,507 per night from 22 May to 23 May
P9,507
per night
22 May - 23 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! (311 reviews)
"A good stay. Clean and quite. Nice pool and fun for the Kidspiration"

Reviewed on May 5, 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! (857 reviews)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"

Reviewed on Nov 19, 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.

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