Pittsfield Travel Guide

Tourist Guide

Pittsfield showing a city
Pittsfield showing heritage elements and flowers
Pittsfield
Pittsfield featuring 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 AU$192 per night from 28 Sept to 29 Sept
AU$192
28 Sept - 29 Sept
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (656 reviews)
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again."

Reviewed on 25 Sept 2025

Berkshire Mountain Lodge
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 AU$184 per night from 5 Oct to 6 Oct
AU$184
5 Oct - 6 Oct
includes taxes & fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (881 reviews)
"It has been more than 10 years since parking garage available"

Reviewed on 23 Sept 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street, Pittsfield, MA
The price is AU$214 per night from 2 Oct to 3 Oct
AU$214
2 Oct - 3 Oct
includes taxes & fees
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are ...
9.4/10 Exceptional! (43 reviews)
"Very nice hotel"

Reviewed on 24 Sept 2025

Holiday Inn Express & 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
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy laundry facilities, a pool table, and in-room washers/dryers. Popular attractions Jiminy ...
9.8/10 Exceptional! (13 reviews)
"Twenty-five family members flew in from around the country for a memorial service in Pittsfield. The Inn allowed us to turn the weekend into a family reunion honoring our father/grandfather. Nine people slept at the Inn and we hosted two BBQ dinners for all. People enjoyed the fire pit, outdoor games ..."

Reviewed on 12 Aug 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
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain ...
9.6/10 Exceptional! (125 reviews)
"Great location for us, grew up nearby. Quiet neighborhood. Comfortable for us as 8 adults. Interesting layout. Second floor rooms have great lighting from skylights and windows. The owner obviously had fun decorating with a lakeside theme. We agree that we would be fine returning to the same home ..."

Reviewed on 10 Sept 2025

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!

Pittsfield, MA
Stay at this vacation home in Pittsfield. Enjoy a fitness center, laundry facilities, and air conditioning. Popular attractions Canoe Meadows Wildlife Sanctuary ...
3-bedroom house in beautiful Berkshires, close to amenities!
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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