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.

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Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundable
$121 nightly
The price is $136 total per night from Mar 23 to Mar 24
$136 total
Mar 23 - Mar 24
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! (847 reviews)
Yes great stay

Reviewed on Feb 18, 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
$103 nightly
The price is $115 total per night from Feb 24 to Feb 25
$115 total
Feb 24 - Feb 25
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 listed their pool was not operational until Jan 31, but learned this was extended upon our arrival on Feb 15. This was an inconvenience as our kids were not happy not to have a pool. Entire hotel need an upgrade as our hot water took about 5 minutes to warm up each time along with other structural ...

Reviewed on Feb 17, 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 Feb 26 to Feb 27
$166 total
Feb 26 - Feb 27
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 ...
9.4/10 Exceptional! (824 reviews)
Room was spotless, staff was amazing! Loved the bathroom setup! Will recommend and stay again!

Reviewed on Feb 9, 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 ...
9.8/10 Exceptional! (16 reviews)
We could reach out to host any time we need and prompt reply was very helpful. House was near and clean and we enjoyed the hot tub and the fire pit. Happy Thanksgiving getaway with huge group was awesome for this place cuz the house was so spacious and many rooms for every one to sleep. Thanks a ...

Reviewed on Nov 30, 2025

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
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! (131 reviews)
The host is vey helpful and the house is so great for large family groups. The kitchens are well-stocked and the bathrooms are very adequate for a lot of people. There are 2 sets of washers and dryers and our group really enjoyed the pool table and the hot tub ( after we figured it out.) The beds ...

Reviewed on Dec 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 MA
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! (128 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
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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