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 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 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.

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is Rp1.068.824 per night from 7 Sept to 8 Sept
Rp1.068.824
Rp1.556.812 total
7 Sept - 8 Sept
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (581 reviews)
"Enjoyed the room, towels and kitchen. I can recommend."

Reviewed on 18 Aug 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
The price is Rp1.155.091 per night from 3 Sept to 4 Sept
Rp1.155.091
Rp1.290.257 total
3 Sept - 4 Sept
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 (767 reviews)
"The bathroom in our room looks like someone was murdered in the bathtub. There were stains on the bottom of the tub."

Reviewed on 10 Aug 2025

FairBridge Inn Express
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 Rp1.770.814 per night from 2 Sept to 3 Sept
Rp1.770.814
Rp1.977.999 total
2 Sept - 3 Sept
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! (863 reviews)
"It was fine , no complaints"

Reviewed on 19 Aug 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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! (1,956 reviews)
"A rare, affordable place in the Berkshires! The scenery is stunning, and we loved the pools (both indoor and out) and fire pit. The staff was friendly, and our room was spacious but dated: the blinds were broken, the doors stuck, the walls were paper thin and our king-size mattress had clearly seen ..."

Reviewed on 18 Aug 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 hot tubs. Our guests praise the property condition in their reviews. Popular ...
8.2/10 Very Good! (964 reviews)
Beautiful Berkshire relaxation!
"From the pleasant staff to the comfy cozy, clean atmosphere of the room, this resort is a definite “go to” experience while vacationing in the Berkshires. The resort attractions are a family fun filled adventures that are great to experience. Our favorite was the ski lift to the top of the mountain ..."

Reviewed on 19 Aug 2025

Jiminy Peak Mountain Resort
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd, Williamstown, MA
Stay at this campsite in Williamstown. Enjoy free parking, breakfast (surcharge) and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
10/10 Exceptional! (3 reviews)
"Perfect place for a relaxing getaway! We loved everything!"

Reviewed on 11 Aug 2025

Huttopia Berkshires
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