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
Stay at this 3-star golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (536 reviews)
"It was a great central spot for our plans in the Berkshires. The place is quiet and the staff is friendly. The rooms are very large with a stocked kitchen, dishwasher, dining table, etc. The pull out sofa has a thinner mattress so don't expect a lot of comfort, but the king bed was good. A/C could ..."

Reviewed on 31 Jul 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
The price is £60 per night from 18 Aug to 19 Aug
£60
18 Aug - 19 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 (759 reviews)
Good enough
"Comfortable for (Dad and Son) a two night trip."

Reviewed on 2 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 £97 per night from 1 Sept to 2 Sept
£97
1 Sept - 2 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! (840 reviews)
"There is some renovation going on at the hotel so some common area appearance is affected and garage is not available at this time due to renovations but they do offer free valet parking which is off site"

Reviewed on 31 Jul 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.
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock, MA
Stay at this family-friendly holiday home in Pittsfield. Enjoy laundry facilities, a pool table and in-room washers/dryers. Popular attractions Alpine Super ...
9.8/10 Exceptional! (11 reviews)
"Amazing Inn. Cozy and everything we needed."

Reviewed on 9 Jun 2025

Hancock Village Inn at 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
Stay at this family-friendly holiday home in Pittsfield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Crane Museum of Papermaking and ...
9.6/10 Exceptional! (124 reviews)
Great neighborhood location near the lakes.
"A beautiful large home with plenty of bedrooms and space to just relax after a long day on the water or catching a show at Tangle Wood. Our family enjoyed the spacious bedrooms and large backyard complete with a fire pit, large hot tub, grilling area and ample seating. This home has two kitchens ..."

Reviewed on 18 Jul 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 Wi-Fi, laundry facilities and concierge services. Popular attractions Crane Museum of Papermaking and Alpine Super ...
9.8/10 Exceptional! (120 reviews)
Beyond expectation - a hidden Gem
"I could not be more satisfied with the experience we had during our short stay. It was actually very nice to be more in the quiet Cove vs the main lake area… Paddling via canoe or kayak to the main lake area and swimming off of the island there was quite special."

Reviewed on 25 Jul 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.

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