Pittsfield

Travel Guide

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

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 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 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.

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is €124 per night from 1 Apr to 2 Apr
€124
1 Apr - 2 Apr
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (872 reviews)
the room was huge - we loved it!!

Reviewed on 11 Mar 2026

Berkshire Mountain Lodge
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 €124 per night from 29 Mar to 30 Mar
€124
29 Mar - 30 Mar
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,000 reviews)
Hotel is going through a renovation which makes the place a little rougher than it’s used to be. No parking or limited parking at entrance of hotel. Valet parking personnel were parking cars on entrance round entrance and in the mourning, they were towing those cars from the property. Not a good ...

Reviewed on 8 Mar 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
The price is €145 per night from 15 Mar to 16 Mar
€145
15 Mar - 16 Mar
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (832 reviews)
Great hotel. Great location. Rooms are very spacious. Staff is always friendly and helpful, especially Andrew at the front desk. A breakfast venue on premises would be a nice addition.

Reviewed on 13 Mar 2026

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.
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 MA
Stay at this cabin in Pittsfield. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
10/10 Exceptional! (129 reviews)
The cabin was perfectly located for a week of exploring the Berkshires and southern Vermont. It is centrally located in the region, but feels private because it is surrounded by trees and set back from the road. It was the best stocked kitchen I've had in a rental. Relaxing by the pond was very peaceful; ...

Reviewed on 30 Sept 2025

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock MA
Stay at this family-friendly holiday home in Pittsfield. Enjoy free Wi-Fi, laundry facilities and a pool table. Popular attractions Jiminy Peak Mountain Resort ...
10/10 Exceptional! (19 reviews)
Really great host - communication was great. House is so close to skiing, can’t beat it

Reviewed on 24 Feb 2026

Hancock Village Inn Near 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 MA
Stay at this family-friendly holiday home in Pittsfield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and ...
9.8/10 Exceptional! (155 reviews)
Everything about this house was perfect! Great location, great amenities, great vibes. Will probably be booking again next year we loved it so much!

Reviewed on 25 Feb 2026

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

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