Pittsfield Travel Guide

Tourist Guide

Pittsfield which includes a city
Pittsfield showing heritage elements and flowers
Pittsfield
Pittsfield showing a church or cathedral
Pittsfield

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 colourful 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 of Herman 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 Theatre, a gilded old theatre that has been fully restored and offers an entertaining programme including music and theatrical performances. The Pittsfield Visitors Centre is found in the theatre’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 Centre. 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 by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
The price is ₹11,148 per night from 27 Jul to 28 Jul
₹11,148
₹12,452 total
27 Jul - 28 Jul
includes taxes & fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (827 reviews)
"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield."

Reviewed on 21 Jul 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 ₹10,939 per night from 28 Jul to 29 Jul
₹10,939
₹12,219 total
28 Jul - 29 Jul
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,011 reviews)
"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."

Reviewed on 18 Jul 2025

Best Western Plus Berkshire Hills Inn & Suites
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
The price is ₹6,141 per night from 6 Aug to 7 Aug
₹6,141
₹6,860 total
6 Aug - 7 Aug
includes taxes & fees
Stay at this business-friendly motel in Pittsfield. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (751 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."

Reviewed on 1 Jul 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.
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 fitness centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,890 reviews)
"I loved the mountains all around, beautiful scenery."

Reviewed on 21 Jul 2025

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 their reviews. Popular ...
8.2/10 Very Good! (950 reviews)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"

Reviewed on 7 Jul 2025

Jiminy Peak Mountain Resort
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo in Lenox. Enjoy free Wi-Fi, free parking and a fitness centre. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (121 reviews)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."

Reviewed on 14 May 2025

The Ponds at Foxhollow
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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