Pittsfield

Travel Guide

Pittsfield featuring a city
Pittsfield showing flowers and heritage elements
Pittsfield
Pittsfield showing a church or cathedral
Pittsfield

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.

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (548 reviews)
"Reallt liked the property. Great location. Would suggest more comfortable chairs outside."

Reviewed on 9 Aug 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
The price is €68 per night from 24 Aug to 25 Aug
€68
24 Aug - 25 Aug
includes taxes & fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (763 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on 2 Aug 2025

FairBridge Inn Express
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
The price is €110 per night from 1 Sept to 2 Sept
€110
1 Sept - 2 Sept
includes taxes & fees
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! (853 reviews)
"A very clean and friendly environment. Staff were efficient and knowledgeable. Would appreciate two more handcap parking spaces at front of hotel. Thank you."

Reviewed on 7 Aug 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy laundry facilities, a pool table, and in-room washers/dryers. Popular attractions Jiminy ...
9.8/10 Exceptional! (12 reviews)
"Amazing Inn. Cozy and everything we needed."

Reviewed on 9 Jun 2025

Hancock Village Inn at Jiminy Peak
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain ...
9.6/10 Exceptional! (124 reviews)
Great neighborhood location near the lakes.
"A beautiful large home with plenty of bedrooms and space to just relax after a long day on the water or catching a show at Tangle Wood. Our family enjoyed the spacious bedrooms and large backyard complete with a fire pit, large hot tub, grilling area and ample seating. This home has two kitchens ..."

Reviewed on 18 Jul 2025

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

Pittsfield
Stay at this cabin in Pittsfield. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
9.8/10 Exceptional! (120 reviews)
Beyond expectation - a hidden Gem
"I could not be more satisfied with the experience we had during our short stay. It was actually very nice to be more in the quiet Cove vs the main lake area… Paddling via canoe or kayak to the main lake area and swimming off of the island there was quite special."

Reviewed on 25 Jul 2025

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
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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