Pittsfield, MA

Travel Guide

A historic building with classical architecture, a traffic light, and a yellow taxi.
A stone building with a red door and a tree with pink flowers in front.
A brick building with a clock and an American flag.
A stone church with arched windows and a central tower, surrounded by trees.
A street lined with autumn trees, a street lamp, and parked cars.

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 colorful 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 Theater, a gilded old theater that has been fully restored and offers an entertaining program including music and theatrical performances. The Pittsfield Visitors Center is found in the theater’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 Center. 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
$114 nightly
The price is $127 total per night from Nov 17 to Nov 18
$127 total
Nov 17 - Nov 18
Total with taxes and fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,215 reviews)
"I had a one BR suite for 4 nights and it was a perfect amount of space for 3 people. Kitchen was very well-equipped and convenient to have for making simple meals and reheating leftovers. While all the cooking utensils/ basics were provided, remember to bring all your oil/ spices as I did. I can't ..."

Reviewed on Oct 19, 2026

Berkshire Mountain Lodge
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
$142 nightly
The price is $158 total per night from Nov 1 to Nov 2
$158 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this family-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms ...
Hotel On North
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

2.5 out of 5
1055 South Street Pittsfield MA
$95 nightly
The price is $106 total per night from Nov 17 to Nov 18
$106 total
Nov 17 - Nov 18
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
Holiday Inn Express & Suites Pittsfield-Lenox-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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,215 reviews)
"I had a one BR suite for 4 nights and it was a perfect amount of space for 3 people. Kitchen was very well-equipped and convenient to have for making simple meals and reheating leftovers. While all the cooking utensils/ basics were provided, remember to bring all your oil/ spices as I did. I can't ..."

Reviewed on Oct 19, 2026

Berkshire Mountain Lodge
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 WiFi, laundry facilities, and concierge services. Popular attractions Jiminy Peak Mountain Resort and Pontoosuc ...
10/10 Exceptional! (147 reviews)
"Wonderful trip! Comfortable and well stocked with everything you could ever need. John was an amazing host!"

Reviewed on Oct 1, 2026

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock MA
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Jiminy Peak Mountain ...
10/10 Exceptional! (22 reviews)
"Our stay at the Hancock Village Inn was spectacular! We rented the Inn for my daughter’s graduation from Williams College. The multitude of bedrooms and bathrooms meant our entire extended family could comfortably stay together. The fully (yes- fully!) stocked kitchen allowed us to cook for our large ..."

Reviewed on Jun 25, 2026

Hancock Village Inn Near Jiminy Peak
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.

Stay near popular Pittsfield attractions

Frequently asked questions

Is Pittsfield worth visiting?
Pittsfield is worth visiting for its standout attractions like Hancock Shaker Village and Bousquet Ski Area. Travelers can also enjoy diverse dining options, including Italian and North American cuisine, and benefit from convenient train access for getting around.
When is the best time to visit Pittsfield?
The best time to visit Pittsfield is from May through September, when the weather is generally mild and pleasant for exploring. For travelers seeking fewer crowds and better value, the quieter months of November through February are a good option, offering a cooler, potentially snowy experience.
What is Pittsfield known for?
Pittsfield is known for its historical and cultural attractions, including the Hancock Shaker Village and the Colonial Theater. Travelers can also find outdoor activities at Bousquet Ski Area and enjoy a strong Italian food culture throughout the city.
What is a good itinerary length for Pittsfield?
A good itinerary length for Pittsfield is two to three days to experience highlights like Hancock Shaker Village, Bousquet Ski Area, and the Colonial Theater. For a more in-depth visit, consider four to five days to enjoy these attractions at a relaxed pace and explore the surrounding area further.
How do you get around Pittsfield?
In Pittsfield, travelers can use train services to get around, with the Pittsfield Intermodal Transportation Center serving as a central point for connections. For getting to specific local destinations, rideshare services are also available for convenient travel.
What are the top things to do in and around Pittsfield?
Pittsfield offers a mix of historical sites, outdoor recreation, and cultural experiences for travelers:


How do I plan a trip to Pittsfield?
Plan your trip to Pittsfield by booking flights and hotels on Expedia. Explore attractions like Hancock Shaker Village, Bousquet Ski Area, and Colonial Theater. For flexible planning, pair outdoor activities with indoor options. Consider a rental car for exploring, or utilize available train services to get around.
What cuisines can you find in Pittsfield?
In Pittsfield you can find New American cuisine, offering dishes like gourmet burgers, creative sandwiches, and fresh salads, alongside grilled meats and seafood. Travelers can also enjoy Italian, North American, Chinese, Mexican, and Mediterranean options, including classic pasta dishes.
Can I book a refundable hotel in Pittsfield?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Pittsfield by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Pittsfield with Expedia?
Expedia makes it easier to plan your Pittsfield trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Pittsfield?
The best choice depends on your travel style. Hotels in Pittsfield can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Pittsfield trip on Expedia?
Once you've booked your Pittsfield trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Pittsfield trip?
Expedia offers customer support before, during, and after your Pittsfield trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Pittsfield?
If it's your first trip to Pittsfield, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Pittsfield hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Pittsfield hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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