Pittsfield Travel Guide

Tourist Guide
Pittsfield showing heritage elements and flowers
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
The price is NZ$231 per night from 6 Jun to 7 Jun
NZ$231
per night
6 Jun - 7 Jun
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (947 reviews)
"To be honest, we stayed here for two nights on our 15-day trip, and I can recall nothing about it, good or bad. So, it must have been OK. No bad memories or unpleasant findings, but no memorable wow factors either. It met our needs adequately. I do recall that the staff was very friendly and helpful ..."

Reviewed on 26 May 2024

Best Western Plus Berkshire Hills Inn & Suites
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
Fully refundable
The price is NZ$247 per night from 11 Jun to 12 Jun
NZ$247
per night
11 Jun - 12 Jun
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 ...
7.8/10 Good! (581 reviews)
"loved how close to downtown the property is, we walked whwre we could. parking garage is closed for renovations but the staff was great and provided free valet and parked our car close or in front of the doors most days to help with us having a small child and my husband using a cane. loved the bar ..."

Reviewed on 18 May 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 NZ$301 per night from 2 Jun to 3 Jun
NZ$301
per night
2 Jun - 3 Jun
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the clean rooms in our reviews. Popular ...
8.8/10 Excellent! (312 reviews)
"A good stay. Clean and quite. Nice pool and fun for the Kidspiration"

Reviewed on 5 May 2024

Berkshire Mountain Lodge
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.
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 helpful staff and the clean rooms in our ...
8/10 Very Good! (858 reviews)
Time in the woods
"Staff were so attentive, even at the late hour we checked in (10pm) the place had everything you need. Amazing views and amenities. Loved it"

Reviewed on 27 May 2024

Jiminy Peak Mountain Resort
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 10 Oct. 2023

Chic Pittsfield Home With A View!
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Sandisfield
Stay at this cabin in Sandisfield. Enjoy a garden, tennis courts, and patios. Popular attractions Otis Ridge and Ashintully Gardens are located nearby.
9.6/10 Exceptional! (30 reviews)
Great place
"We loved our time, very cozy cabin"

Reviewed on 31 Mar. 2024

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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.

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