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.

Hotel On North
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
The price is ₹9,294 per night from 27 Apr to 28 Apr
₹9,294
₹10,382 total
includes taxes & fees
27 Apr - 28 Apr
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (708 reviews)
"Lovely large rooms"

Reviewed on 24 Apr 2025

Hotel On North
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 ₹9,294 per night from 28 Apr to 29 Apr
₹9,294
₹10,382 total
includes taxes & fees
28 Apr - 29 Apr
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! (774 reviews)
"Very nice"

Reviewed on 12 Apr 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3 out of 5
8 Dan Fox Dr, Pittsfield, MA
The price is ₹8,442 per night from 8 May to 9 May
₹8,442
₹11,334 total
includes taxes & fees
8 May - 9 May
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! (457 reviews)
"Fully equipped kitchen with everything needed to cook a family meal. Pool and hot tub were wonderful. Staff very helpful."

Reviewed on 21 Apr 2025

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.
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 in-room massages. Our guests praise the helpful staff in ...
8.6/10 Excellent! (1,797 reviews)
"What a beautiful place. Could not be more beautiful and we are so satisfied. We will be back!"

Reviewed on 21 Apr 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! (928 reviews)
Great value, good base location
"Last minute find. Room was tidy/no odors. The kitchen was complete and cute wood art made the place feel cozy. The spare roll away bed was delivered as requested, and surprisingly comfortable. Traveled with hubby and 9 year old between seasons to hit Bash Bish. Will stay here again to visit ..."

Reviewed on 18 Apr 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! (120 reviews)
"Very comfortable property in a lovely setting"

Reviewed on 18 Dec 2024

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.

Popular places to visit

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4/5 - Good

Verified traveller

Visited Soda Chef for breakfast - recommend the pancakes and the owners are very welcoming

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