Pittsfield, MA

Travel Guide
Pittsfield featuring flowers and heritage elements
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.

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
The price is $147 per night from Aug 25 to Aug 26
$147
includes taxes & fees
$131 per night
Aug 25 - Aug 26
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Berkshire Museum and ...
7.8/10 Good! (612 reviews)
Parking Could Be Better!!!
"I had a quiet stay & everything was clean and tidy. The only thing I didn’t like was that I had to park down the street at the bank. But besides that I was satisfied with my room."

Reviewed on Jul 22, 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is $227 per night from Jul 28 to Jul 29
$227
includes taxes & fees
$205 per night
Jul 28 - Jul 29
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and Guido's Marketplace ...
8.8/10 Excellent! (339 reviews)
"We arrived after dark on Tuesday and checked out Wednesday morning; so we didn't get to experience much. Compared to some we've seen the rooms are modern, enormous, and comfortable. Staffing is efficient (no overnight front desk; guests strip beds and put out trash when leaving). The full kitchen ..."

Reviewed on Jul 25, 2024

Berkshire Mountain Lodge
FairBridge Inn Express
FairBridge Inn Express
2.5 out of 5
16 Cheshire Road, Pittsfield, MA
The price is $88 per night from Jul 28 to Jul 29
$88
includes taxes & fees
$79 per night
Jul 28 - Jul 29
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 ...
5.2/10 (603 reviews)
"We had a peaceful night's rest and felt secure. Our room was clean, beds comfy, and bathroom updated. The outside appearance and the room doors could use some help."

Reviewed on Jul 21, 2024

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.
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
Pittsfield
Stay at this vacation home in Pittsfield. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Tanglewood Music Center and Bousquet Ski Area ...
9/10 Wonderful! (4 reviews)
Great getaway house
"Nicely decorated and clean. It had everything we needed, including kitchen supplies and detergent for the washer/dryer. Great rental for our family getaway."

Reviewed on Oct 10, 2023

Chic Pittsfield Home With A View!
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Popular attractions Jiminy Peak Mountain ...
8.6/10 Excellent! (1,686 reviews)
"We had a great stay!"

Reviewed on Jul 17, 2024

Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3 out of 5
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 bars/lounges. Our guests praise the property condition in our reviews. Popular ...
8/10 Very Good! (879 reviews)
"Only stayed a night but kids liked the pool and it was close to the adventure park"

Reviewed on Jul 23, 2024

Jiminy Peak Mountain Resort
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 27.32919254658385%
4 - Good
75
" "4 - Good 46.58385093167702%
3 - Okay
39
" "3 - Okay 24.22360248447205%
2 - Disappointing
1
" "2 - Disappointing 0.6211180124223602%
1 - Terrible
2
" "1 - Terrible 1.2422360248447204%

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