Pittsfield, MA

Travel Guide

Pittsfield featuring a city
Pittsfield featuring flowers and heritage elements
Pittsfield
Pittsfield featuring 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 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.

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
$118 nightly
The price is $132 total per night from Jul 13 to Jul 14
$132 total
Jul 13 - Jul 14
Total includes taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,008 reviews)
"I didn’t like the AC. It was too cold even when I raiised the temperature and switched on and off all night. The breakfast could have been more interesting but otherwise the hotel was pleasant."

Reviewed on Jun 29, 2025

Best Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3 out of 5
One West Street, Pittsfield, MA
$123 nightly
The price is $137 total per night from Jul 24 to Jul 25
$137 total
Jul 24 - Jul 25
Total includes taxes and 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! (801 reviews)
"Quick check in. Room was clean, beds were comfortable. Employees were pleasant. Free valet was a big plus +++"

Reviewed on Jun 28, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
FairBridge Inn Express
FairBridge Inn Express
2.5 out of 5
16 Cheshire Road, Pittsfield, MA
$70 nightly
The price is $79 total per night from Jul 10 to Jul 11
$79 total
Jul 10 - Jul 11
Total includes taxes and 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 ...
5.4/10 (732 reviews)
"Shampoo and toilet paper should have been In the room."

Reviewed on Jun 29, 2025

FairBridge Inn Express
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.
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! (120 reviews)
great house!
"Lovely home. Plenty of room for all of us (11 adults, 2 children). Generally very clean. Plenty of cooking materials, linens, etc. T.v. with huge screen. Two kitchens plus bbq grill. Nice location. Negatives: - Stove tops and oven were not clean. Oven smoked when we first turned it on and the smoke ..."

Reviewed on May 29, 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! (117 reviews)
Relaxing get away
"5 stars all around very relaxing and a great location. John is a great host too very accommodating!"

Reviewed on Jun 24, 2025

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
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! (11 reviews)
"Amazing Inn. Cozy and everything we needed."

Reviewed on Jun 9, 2025

Hancock Village Inn at Jiminy Peak
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