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Things To Do In Pittsfield, Massachusetts With Your Kids – A Weekend Visitor’s Guide

Nestled in the heart of the scenic Berkshires, Pittsfield, Massachusetts, stands as a gem for tourists seeking a blend of cultural richness, natural beauty, and historical depth. This charming city, with its picturesque landscapes and vibrant community, beckons visitors to immerse themselves in a unique and enriching experience.

Things To Do In Pittsfield, Massachusetts With Your Kids – A Weekend Visitor’s Guide

Whether it’s exploring the intriguing exhibits at the Berkshire Museum, taking a leisurely hike through the lush trails, or enjoying the robust arts and theater scene, Pittsfield offers a diverse array of attractions. Its streets, lined with historic landmarks and modern amenities, create a perfect backdrop for an unforgettable getaway.

berkshire family vacation

Why Pittsfield?

Pittsfield, Massachusetts, is a wonderful destination for families for several reasons:

  1. Cultural Attractions: Pittsfield is home to a variety of cultural attractions such as the Berkshire Museum, which offers a mix of art, history, and natural science exhibits, making it enjoyable for all ages.
  2. Outdoor Activities: The city is located in the Berkshires, an area known for its beautiful natural scenery. Families can enjoy outdoor activities such as hiking, biking, and during the winter, skiing and snowboarding nearby.
  3. Historical Significance: Pittsfield has a rich history, and families can learn about it through various historic sites and landmarks. The Hancock Shaker Village, for instance, is an open-air museum that offers a glimpse into the life of the Shaker community.
  4. Theater and Arts: The city has a vibrant arts scene, including the Barrington Stage Company, known for high-quality theater productions. The Colonial Theatre is another historic venue offering a variety of performances.
  5. Family-Friendly Festivals: Throughout the year, Pittsfield hosts several festivals and events that are family-friendly, such as street fairs, concerts, and seasonal celebrations.
  6. Educational Opportunities: Many of the attractions in Pittsfield are not only entertaining but also educational, offering learning experiences for children in a fun and interactive way.
  7. Proximity to Other Attractions: Pittsfield is also a great base for exploring other parts of the Berkshires, including nearby towns with their own unique attractions.

Overall, Pittsfield is a great mix of educational, cultural, and outdoor activities, making it an ideal destination for families looking for a diverse and enriching experience.

Where To Eat

thrive diner

Thrive Diner – 145 Wahconah St., Pittsfield

  • Thrive offers a strictly plant-based, vegan and raw foods menu with numerous nut-free and gluten-free options. Vegans, vegetarians, and carnivores alike can select from dozens of high-quality, organic menu options: soups, salads, sandwiches, buddha bowls, entrees, and desserts.
district kitchen

District Kitchen & Bar – 40 West St, Pittsfield,

  • The restaurant has a top-notch beer, wine, and cocktail program with a rotating selection of craft beer, a carefully curated wine list, and inventive seasonal cocktails prepared with care and consideration of classical mixology techniques.
Ayelada Frozen Yogurt

Ayelada Frozen Yogurt – 505 East Street – Pittsfield

  • Fresh, local, and real, this is a great family spot for a dessert run. It’s ‘farm to cone,’ using locally sourced ingredients.
Dottie’s Coffee Lounge

Dottie’s Coffee Lounge – 444 N St., Pittsfield

  • An upbeat shop offering everything from espresso drinks to breakfast and lunch options, including the local specialty Bear Butter – a rival to nut butters everywhere. 
Proprietor’s Lodge

Proprietor’s Lodge – 22 Waubeek Rd., Pittsfield 

  • A Completely Renovated Event Space And Restaurant, Located On Pontoosuc Lake With Views Of Mt. Greylock!  Serving Lunch, Dinner And Sunday Brunch!

Sibaritas – 1264 East St., Pittsfield 

  • Some of the best food in the city – everything is made with love and with the freshest ingredients.

Misty Moon Diner – 565 Dalton Avenue, Pittsfield

  • Food is made to order, so sit back, relax and enjoy our memorabilia collection, including a custom Harley Davidson. Proudly serving the Berkshires since 1996, Misty Moonlight Diner offers a variety of fresh, homemade food at reasonable prices.

Where To Stay

holiday inn pool

Holiday Inn & Suites – One West Street, Pittsfield, MA 01201 

One of the best perks this hotel offers is their pool encased in an oversized atrium. My children swam nightly and really enjoyed winding down with a quick dip.

What To Do

Herman Melville’s Arrowhead

Herman Melville’s Arrowhead – 780 Holmes Road in Pittsfield 

  • The house, barns, and grounds are watched over by the Berkshire County Historical Society. Since construction in the 1780s, there have been many changes to interpret Herman Melville’s ownership (1850-1863) using the best preservation practices.
Hancock Shaker Village

Hancock Shaker Village – 1843 W. Housatonic St., Pittsfield

  • A landmark destination of 750 acres, 20 historic Shaker buildings, and over 22,000 Shaker artifacts. On the National Historic Register, it is the most comprehensively interpreted Shaker site in the world and the oldest working farm in the nation. 
Berkshire Museum

Berkshire Museum – 39 South St., Pittsfield

  • Located in the heart of Pittsfield, Berkshire Museum combines art, science, and history in ways that spark creativity, inspire innovation, and celebrate a life-long love of learning. With special exhibits and rotating collections that explore the human experience, an aquarium filled with aquatic and reptile friends, exciting special events, and engaging weekly programming for all ages, there is so much to see and do.

Are there any special events or festivals in Pittsfield?

Pittsfield, Massachusetts, hosts a variety of special events and festivals throughout the year, offering a rich array of experiences for both locals and visitors. Here are ten notable events and when they typically take place:

  1. 10×10 Upstreet Winter Festival: Held in February, this arts festival is a collaboration among several organizations, bringing thousands of people downtown for ten days of cultural activities (Feb 16-26, 2023).
  2. 3rd Thursdays Street Festival: Running from May to September, this downtown street festival features music, food, and vendors, drawing crowds from all over the county and beyond, occurring on the third Thursday of each month.
  3. 4th of July Parade: A beloved tradition since 1824, the parade includes modern floats and marching bands from across New England, attracting thousands of spectators.
  4. Baby Animals at Hancock Shaker Village: Celebrate spring by meeting baby farm animals like lambs, piglets, calves, chicks, and goat kids, while touring the historic village and enjoying various activities.
  5. Berkshire International Film Festival: Taking place in both Great Barrington and Pittsfield, this world-class festival showcases independent feature, documentary, short, and family films along with panel discussions and special events.
  6. Celebration of Black Voices: Started by Barrington Stage Company in 2021, this week-long summer event celebrates local Black artists and culture.
  7. Pittsfield CityJazz Festival: Formed in 2005, this festival presents mainstream and traditional jazz in a downtown setting.
  8. Pride Festival: Berkshire County’s annual public LGBTQI Pride celebration occurs in June in Pittsfield, promoting LGBTQI equality through various community organizing efforts.
  9. WordXWord Festival: A year-round event using spoken word, poetry, and storytelling to celebrate diversity, empower individuals, and foster understanding and empathy.
  10. Festive Frolic: Scheduled for December 1-3, this event includes activities like the Park Square Tree Lighting Ceremony, The Grinch at Otto’s, free admission to the Festival of Trees, a Holiday First Fridays Artswalk, Pictures with Santa, and more.

These events reflect Pittsfield’s vibrant cultural scene and its commitment to celebrating diversity and arts in the community


Best things to do near Pittsfield/in neighboring Berkshire towns:

  • Balderdash Cellars
    • Winery right outside Pittsfield city limits in Richmond (10 mins West) – you may bring your own NA beverages + food in addition to purchasing alcoholic beverages on-site.
    • Live music from 1-4 + 5-8pm on Saturday and 2-5pm on Sunday, tasting room is open from 12-8 and 12-5, respectively.
  • Norman Rockwell Museum
    • In Stockbridge (30 mins South of Pittsfield), the museum highlights the power of American illustration art to reflect and shape society, and advances the enduring values of kindness, respect and social equity portrayed by Norman Rockwell. Kids are free!
  • Mass MoCA
    • Located in North Adams (40 mins North of Pittsfield), the museum of contemporary art has vast galleries and a stunning collection of performance venues for music, sculpture, dance and film.
    • There is free parking, a full-service restaurant, delicious ice cream and an innovative microbrewery that spotlights locally malted grains and hops grown in the Berkshire valley.
  • Clark Art Institute
    • In Williamstown (35 minutes North of Pittsfield), this free art museum has a 140-acre campus spotlighting permanent collection galleries and special exhibitions amidst a winter wonderland.
  • Tanglewood
    • Boston Symphony Orchestra’s summer locale and outdoor concert venue – James Taylor, a friend of the Berkshires, hosts a concert every summer. 
  • Jacob’s Pillow
    • A world-renowned dance venue, a professional dancer’s dream. Live for the summer season and they also perform at smaller pop-up performances in the Berkshire towns.

What outdoor activities are available in Pittsfield?

Pittsfield offers a variety of outdoor activities to enjoy, especially given its picturesque location in the Berkshires. Here are five popular outdoor activities:

  1. Hiking: The area is known for its beautiful hiking trails, which are suitable for all skill levels and offer scenic views and a chance to enjoy the natural beauty of the Berkshires.
  2. Biking: There are numerous biking trails and paths catering to casual riders and more experienced cyclists.
  3. Fishing: The region’s lakes, rivers, and streams offer excellent fishing opportunities.
  4. Boating and Kayaking: The local water bodies provide perfect settings for boating and kayaking, allowing visitors to explore the serene waters.
  5. Skiing and Snowboarding: In the winter, the nearby ski resorts become a hub for skiing and snowboarding, attracting enthusiasts from all over.

I hope I’ve convinced you to check out Pittsfield in the Berkshires! Your kids will love places like the Berkshire Museum. Plus, there are so many options to do outdoors – like hiking, biking, and even fishing.

And if you’re into winter sports, the skiing and snowboarding nearby are top-notch. It’s a place where everyone in the family can find something fun to do, making your trip memorable and one for the books. Pittsfield is a must-visit!

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