Pittsfield, MA

Travel Guide

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

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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$115 nightly
The price is $128 total per night from Apr 12 to Apr 13
$128 total
Apr 12 - Apr 13
Total with taxes and fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (871 reviews)
the room was huge - we loved it!!

Reviewed on Mar 11, 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
$122 nightly
The price is $137 total per night from Mar 13 to Mar 14
$137 total
Mar 13 - Mar 14
Total with taxes and fees
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 ...
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 Mar 8, 2026

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

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
$149 nightly
The price is $166 total per night from Mar 15 to Mar 16
$166 total
Mar 15 - Mar 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (830 reviews)
Great one night experience, hotel was quiet and clean. Room was cozy and comfortable as well. Rate was very reasonable to make for a affordable ski trip

Reviewed on Mar 8, 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.
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

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

Reviewed on Feb 24, 2026

Hancock Village Inn Near Jiminy Peak
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 WiFi, a fitness center, 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 Sep 30, 2025

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
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
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain ...
9.8/10 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 Feb 25, 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

4
Top Destination
5 - Excellent
44
5 - Excellent 27%
4 - Good
75
4 - Good 47%
3 - Okay
39
3 - Okay 24%
2 - Disappointing
1
2 - Disappointing 1%
1 - Terrible
2
1 - Terrible 1%

5/5 - Excellent

Verified traveler

Skiing and snow tubing are AMAZING! So worth it.

5/5 - Excellent

Verified traveler

We were in Pittsfield for a funeral. No time for other visits than for our friends. We really appreciated the architecture of the buildings. We will definitely return.

4/5 - Good

Verified traveler

Seem like a very nice town from what we saw, I would like to explore in more on my next trip.

3/5 - Okay

Verified traveler

Old city

5/5 - Excellent

Verified traveler

Great small town on the outskirts of Lenox and Stockbridge. Plenty of food options.

5/5 - Excellent

Verified traveler

Pittsfield and the Berkshires are fabulous!

Cities near Pittsfield

Explore a world of travel with Expedia