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.

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
$113 nightly
The price is $126 total per night from Nov 9 to Nov 10
$126 total
Nov 9 - Nov 10
Total with taxes and fees
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 ...
9/10 Wonderful! (745 reviews)
Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you

Reviewed on Nov 2, 2025

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
$98 nightly
The price is $109 total per night from Nov 21 to Nov 22
$109 total
Nov 21 - Nov 22
Total with 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! (938 reviews)
Spotless and friendly staff

Reviewed on Nov 2, 2025

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

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
$133 nightly
The price is $149 total per night from Nov 12 to Nov 13
$149 total
Nov 12 - Nov 13
Total with taxes and fees
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (788 reviews)
Lovely hotel in the middle of a non very busy town.

Reviewed on Oct 31, 2025

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 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! (14 reviews)
Great place for a family reunion. Lots of bedrooms and bathrooms. Kitchen is large & well equipped

Reviewed on Oct 17, 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! (127 reviews)
If you're traveling with family and kids, this house is a gem. So many toys outside and inside. The owner was very quick to respond to any questions and we had a great time. The kitchen was well equipped.

Reviewed on Sep 21, 2025

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

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 ...
9.8/10 Exceptional! (62 reviews)
Beautiful home in a great location in the Berkshires! We would absolutely return during the summer months to take advantage of the lake, but the fall foliage in October was beautiful.

Reviewed on Oct 30, 2025

Lake Front Home in Heart of the Berkshires Near 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

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