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The Best Berkshire Attractions For Families

The Berkshires, located in western Massachusetts, is a picturesque region known for its beautiful landscapes, cultural attractions, and outdoor activities, making it an ideal destination for family trips.

Hancock Shaker Village

Here’s a list of family-friendly activities in the Berkshires that will be sure to keep everyone occupied and happy:

  1. The Mount, Edith Wharton’s Home (Lenox)
    • Explore the beautifully restored home and gardens of the famous author Edith Wharton. Engage in a family-friendly tour that highlights the history and architecture of this Gilded Age mansion.
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  2. Berkshire Scenic Railway Museum (Lenox)
    • Take a scenic train ride through the Berkshire hills. This museum offers educational exhibits and vintage train rides that provide a glimpse into the region’s railroading history.
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  3. Mass MoCA (North Adams)
    • One of the largest centers for contemporary visual and performing arts in the U.S. It offers innovative and engaging art exhibitions that can captivate visitors of all ages.
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  4. Norman Rockwell Museum (Stockbridge)
    • Home to the world’s largest collection of original Norman Rockwell art. This museum offers a look into American life through the eyes of a beloved illustrator, with family-friendly programs and interactive exhibits.
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  5. Berkshire Botanical Garden (Stockbridge)
    • Explore various plant collections and beautiful gardens spread over 24 acres. They offer educational programs and special events for families and children.
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  6. Hancock Shaker Village (Pittsfield)
    • A living history museum that brings the Shaker community to life through tours, demonstrations, and hands-on activities for kids.
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  7. Berkshire Museum (Pittsfield)
    • Offers a unique blend of art, history, and natural science exhibits, making learning fun for children. The museum features interactive exhibits that engage young minds.
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  8. Mount Greylock State Reservation (Adams)
  9. Tanglewood (Lenox)
    • The summer home of the Boston Symphony Orchestra. Enjoy family-friendly concerts and music events in a relaxed outdoor setting.
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  10. Ramblewild Aerial Adventure Park (Lanesborough)
    • A forest adventure park with zip lines, high ropes courses, and other thrilling activities set in a beautiful forest canopy.
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  11. Jacob’s Pillow Dance Festival (Becket)
    • Experience world-class dance performances and workshops at this renowned dance center and festival.
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  12. Pleasant Valley Wildlife Sanctuary (Lenox)
    • Explore miles of trails through forests, meadows, and wetlands. Look for beavers, otters, and a variety of birds.
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  13. Berkshire HorseWorks (Richmond)
    • Provides equine-assisted therapy and horseback riding experiences. Great for families interested in learning about horses and engaging in therapeutic activities.
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  14. Chesterwood (Stockbridge)
    • The summer home and studio of Daniel Chester French, sculptor of the Lincoln Memorial statue. The estate offers beautiful gardens and art exhibitions.
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  15. The Clark Art Institute (Williamstown)
    • An art museum with an extensive collection of paintings, sculpture, and decorative arts. The Clark also offers family programming and outdoor concerts in the summer.
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  16. Williams College Museum of Art (Williamstown)
    • Offers a diverse collection of art ranging from ancient to modern. Engaging exhibitions and programs are designed to spark conversations among families.
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  17. Ashuwillticook Rail Trail (Adams to Lanesborough)
    • A scenic 12.7-mile trail perfect for biking, walking, and rollerblading, with beautiful views of the surrounding mountains and Cheshire Reservoir.
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  18. Naumkeag (Stockbridge)
    • A Gilded Age mansion with stunning gardens and landscape architecture. Offers house tours and garden walks suitable for all ages.
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  19. Berkshire Grown Farmers Markets (Various Locations)
    • Visit local farmers’ markets to enjoy fresh produce, artisanal foods, and crafts. Great for teaching kids about local agriculture and healthy eating.
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  20. Berkshire Theatre Group (Stockbridge and Pittsfield)
  21. Sheffield Covered Bridge (Sheffield)
    • Visit this historic landmark for a picturesque view and a chance to explore the surrounding area’s natural beauty.
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  22. Windsor Lake (North Adams)
    • Enjoy swimming, fishing, kayaking, and picnicking at this beautiful lake. They also host a series of free concerts during the summer months.
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  23. Balance Rock State Park (Pittsfield)
    • Famous for its 165-ton limestone boulder precariously balanced on bedrock, this park offers hiking trails and picnic areas.
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  24. Bartholomew’s Cobble (Sheffield)
    • Offers hiking trails through unique geological formations and a variety of habitats. Great for nature walks and bird watching.
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  25. Mount Everett State Reservation (Sheffield)
    • Offers hiking trails to the summit for panoramic views. It’s an excellent spot for families who enjoy outdoor adventures.
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  26. Bidwell House Museum (Monterey)
    • A colonial history museum set in a beautifully restored 1760s homestead. Offers guided tours that bring colonial America to life.
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  27. Berkshire Co-op Market (Great Barrington)
    • A community-owned cooperative offering local, organic, and sustainable foods. Great for grabbing a healthy snack or ingredients for a picnic.
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These destinations offer educational, recreational, and cultural experiences for families visiting the Berkshires. Check each website for the latest information on opening hours, ticket prices, and any special events that might interest your family.

Catamount Mountain

Ski Areas In The Berkshires

The Berkshires in western Massachusetts are popular destinations for skiing enthusiasts, offering a variety of slopes suitable for different skill levels. It’s one of the best things you can do during the colder months.

Enjoy a perfect getaway in this dynamic region by booking a vacation around one of these snowy escape retreats. Here are some notable skiing options in the region:

  1. Jiminy Peak Mountain Resort (Hancock)
    • Jiminy Peak is the largest ski and snowboard resort in southern New England. It offers 45 trails and 9 lifts, catering to all levels of skiers and snowboarders. The resort features a vertical drop of 1,150 feet and includes a variety of terrain, from gentle beginner slopes to challenging expert trails. Night skiing is available on 21 trails. The resort also boasts an energy-efficient snowmaking system and a wind turbine that generates renewable energy for the resort.
    • Location: Hancock, MA
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  2. Bousquet Ski Area (Pittsfield)
    • Bousquet Ski Area, nestled within the Berkshire Hills, offers a family-friendly skiing experience with a mix of beginner, intermediate, and advanced trails. The ski area features 23 trails, 5 lifts, and a vertical drop of 750 feet. Bousquet is known for its affordable skiing options and also provides night skiing on select trails. In addition to skiing and snowboarding, the area offers snow tubing for added winter fun.
    • Location: Pittsfield, MA
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  3. Ski Butternut (Great Barrington)
    • Ski Butternut is a family-oriented ski resort offering 22 trails and 10 lifts, with a 1,000-foot vertical drop. The resort caters to all skill levels, from beginners to advanced skiers and snowboarders. It is known for its well-groomed trails, efficient snowmaking, and a welcoming atmosphere. Ski Butternut also features a terrain park, tubing center, and ski school for both children and adults.
    • Location: Great Barrington, MA
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  4. Otis Ridge Ski Area (Otis)
    • Otis Ridge is a smaller, more intimate ski area in the Berkshires, perfect for families and those new to skiing or snowboarding. It offers a variety of trails primarily suited for beginner and intermediate skiers. The ski area is known for its friendly atmosphere and personalized attention at its ski school. Otis Ridge also provides night skiing and a cozy ski lodge for relaxing after a day on the slopes.
    • Location: Otis, MA
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  5. Catamount Mountain Resort (Hillsdale, NY / South Egremont, MA)
    • Straddling the border between New York and Massachusetts, Catamount offers 36 trails and 7 lifts, with a vertical drop of 1,000 feet. The resort features a diverse range of trails, including the longest run in the Berkshires, and caters to all levels of skiers and snowboarders. Catamount has recently made significant improvements, including updated lifts and expanded terrain. It also offers night skiing on more than 15 trails.
    • Location: Hillsdale, NY, and South Egremont, MA
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These ski resorts in the Berkshires offer a variety of winter sports experiences, from gentle beginner slopes to more challenging terrains for experienced skiers and snowboarders. Each resort has its unique charm and set of amenities, ensuring something for everyone, whether you’re looking for a family-friendly day on the slopes or an adventurous skiing experience.

small towns

The Small Towns That Make Up The Berkshires of Massachusetts

The Berkshires, a picturesque region in western Massachusetts, is dotted with charming small towns, each offering its unique blend of natural beauty, cultural richness, and historical significance. Among these, Lenox stands out as a cultural hub, home to Tanglewood, the summer home of the Boston Symphony Orchestra, and several Gilded Age mansions like The Mount, Edith Wharton’s estate. 

Nearby, Stockbridge is immortalized in Norman Rockwell’s art, capturing quintessential small-town America, and houses the Norman Rockwell Museum. Great Barrington, with its vibrant Main Street, offers a mix of local boutiques, restaurants, and the historic Mahaiwe Performing Arts Center. Williamstown is known for its academic atmosphere, anchored by Williams College, and cultural institutions like the Clark Art Institute and Williams College Museum of Art. 

Pittsfield, the largest town in the Berkshires, serves as the region’s commercial center and hosts cultural venues like the Berkshire Museum and the Colonial Theatre. Other noteworthy towns include Hancock, known for Jiminy Peak Mountain Resort; North Adams, home to the Massachusetts Museum of Contemporary Art (Mass MoCA); and Sheffield, which boasts pastoral landscapes and historic homes. 

These hidden gems, along with others like Lee, Adams, and Dalton, contribute to the Berkshires’ reputation as a retreat for nature lovers, history lovers, artists, and anyone seeking the tranquility and inspiration of New England’s countryside. Each location can be enjoyed any time of year. 

10 Restaurants To Visit In The Berkshires

berkshire restaurants

The Berkshires boasts a vibrant culinary scene, featuring an array of dining options that highlight local ingredients, offer cozy atmospheres, and provide unique culinary experiences. Here are 10 restaurants you should consider visiting when in the Berkshires – including casual and fine restaurants:

  1. Café Adam (Great Barrington)
    • An upscale, yet cozy spot known for its creative American cuisine with a focus on local and organic ingredients. The menu changes seasonally to reflect the freshest produce available.
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  2. Mezze Bistro + Bar (Williamstown)
    • Offers contemporary American cuisine with a nod to the Mediterranean. Mezze is committed to supporting local farmers and producers, ensuring a fresh and seasonal menu.
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  3. The Old Inn On The Green (New Marlborough)
    • Nestled in a quaint 18th-century building, this restaurant provides a unique dining experience with candlelit rooms and a menu that features refined New England cuisine.
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  4. Alta Restaurant & Wine Bar (Lenox)
    • Offers a Mediterranean-inspired menu along with an extensive wine list. The atmosphere is casual yet elegant, perfect for a special night out.
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  5. Nudel Restaurant (Lenox)
    • A creative American pasta restaurant that uses local and seasonal ingredients to produce inventive and flavorful dishes. The menu changes daily, reflecting the chef’s inspiration and the best available ingredients.
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  6. John Andrews Farmhouse Restaurant (South Egremont)
    • Set in a charming 18th-century farmhouse, this restaurant specializes in farm-to-table cuisine, highlighting the best of Berkshire and Hudson Valley products.
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  7. Baba Louie’s (Pittsfield and Great Barrington)
    • Known for its delicious sourdough pizza and organic salads, Baba Louie’s is a favorite among locals and visitors alike for a casual and satisfying meal.
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  8. The Dream Away Lodge (Becket)
    • A quirky and eclectic restaurant known for its bohemian vibe, live music, and hearty, home-cooked meals. It’s a place where history, art, and community converge.
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  9. The Prairie Whale (Great Barrington)
    • A laid-back, hip eatery offering a fresh take on comfort food classics, crafted with locally sourced ingredients and a keen attention to detail.
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  10. Chez Nous Bistro (Lee)
    • A chef-owned French bistro that serves up classic French dishes along with seasonal specialties, in a warm and inviting atmosphere. The commitment to quality and the cozy setting make for a memorable dining experience.
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Each restaurant offers a distinct taste of the Berkshires’ culinary diversity, from upscale dining to casual comfort food, emphasizing the region’s rich agricultural heritage and the chefs’ innovative spirit. Check their websites or contact them for current menus, opening hours, and reservation policies.

Ashuwillticook Rail Trail

What can a nature lover do in the Berkshires? 

For nature enthusiasts, the Berkshires offer an abundance of activities set amidst its scenic hills, lush forests, and serene water bodies. Hiking is a popular pursuit, with trails ranging from the gentle paths at Pleasant Valley Wildlife Sanctuary in Lenox, where birdwatching opportunities abound, to the more challenging hikes up Mount Greylock, Massachusetts’ highest peak, offering panoramic views that stretch to five states. 

The region’s numerous state parks and reserves, such as the Mount Everett State Reservation and Beartown State Forest, provide ample space for outdoor exploration, including camping, fishing, and kayaking in the serene lakes and rivers. The Ashuwillticook Rail Trail offers a more leisurely pace for walking, biking, and rollerblading along a scenic route that follows the old railroad tracks from Lanesborough to Adams, passing through picturesque landscapes and by Cheshire Reservoir. 

For those interested in botany or seeking tranquility, the Berkshire Botanical Garden in Stockbridge showcases beautifully curated gardens with native and exotic plants. Winter transforms the Berkshires into a snowy wonderland, with opportunities for cross-country skiing and snowshoeing in areas like Notchview Reservation in Windsor. 

Cultural Appreciation 

berkshire museum

The Berkshires region is not only celebrated for its natural beauty but also for its rich cultural and artistic heritage, with numerous museums that cater to a variety of interests. Here are some notable museums in the Berkshires:

  1. Mass MoCA (Massachusetts Museum of Contemporary Art) – Located in North Adams, Mass MoCA is one of the largest centers for contemporary visual and performing arts in the United States. The museum occupies a vast complex of 19th-century factory buildings and offers an extensive array of exhibitions, music, theater, and dance performances.
  2. Norman Rockwell Museum – Situated in Stockbridge, this museum houses the world’s largest and most significant collection of Norman Rockwell’s work, including 998 original paintings and drawings. The museum also explores the work of other American illustrators.
  3. The Clark Art Institute – In Williamstown, The Clark is both an art museum and a distinguished center for research and higher education, known for its intimate galleries and stunning natural environment. Its collection includes European and American paintings, sculpture, prints, drawings, photographs, and decorative arts from the Renaissance to the early 20th century.
  4. Berkshire Museum – Located in Pittsfield, the Berkshire Museum combines art, history, and natural science to provide a wide range of educational programs. It features a diverse collection, from ancient artifacts to contemporary art, including a notable aquarium.
  5. Williams College Museum of Art (WCMA) – This museum in Williamstown is known for its dynamic exhibitions and programs that integrate the visual arts into the Williams College curriculum, emphasizing multidisciplinary approaches.
  6. Hancock Shaker Village – Near Pittsfield, this living history museum brings the Shaker community to life. The village includes 20 historic buildings, rich collections of Shaker furniture and artifacts, and offers a variety of workshops and demonstrations.
  7. Frelinghuysen Morris House & Studio – In Lenox, this museum celebrates American abstract artists George L.K. Morris and Suzy Frelinghuysen, showcasing their work in a modernist home and studio that they designed in the Bauhaus style.
  8. Bidwell House Museum – Located in Monterey, this beautifully restored 18th-century house offers a glimpse into colonial America and the early history of the Berkshires through its architecture, furnishings, and surrounding gardens and trails.
  9. Chesterwood – The summer home, studio, and gardens of Daniel Chester French, the sculptor of the Lincoln Memorial, are located in Stockbridge. The site offers insights into French’s creative process and showcases his sculptures in a picturesque setting.
  10. The Mount, Edith Wharton’s Home – In Lenox, this historic estate was the home of the Pulitzer Prize-winning author Edith Wharton. The house and gardens are open to the public, offering a window into Wharton’s life and work, as well as the elegance of the Gilded Age.

These museums not only celebrate the Berkshires’ natural and historical significance but also its longstanding commitment to arts, culture, and education, making it a unique and enriching destination for visitors.

ultimate berkshire vacation

Are you ready to plan the Ultimate Berkshire Vacation?

The Berkshires truly shines as a heartwarming family getaway, weaving together the enchantment of nature’s playground with a tapestry of cultural gems. Now is the perfect time to get to know the region. Each trail hike, from the majestic peaks of Mount Greylock to the serene paths along the Ashuwillticook Rail Trail, becomes a shared adventure, creating stories that your family will cherish. The region’s museums, like the vibrant Mass MoCA and the charming Norman Rockwell Museum, aren’t just places to visit; they’re experiences that spark curiosity and creativity in both the young and the young at heart. What a beautiful place! 

It’s in the Berkshires where the simplicity of a family picnic by a scenic lake blends seamlessly with the thrill of exploring the arts and history, making every moment feel specially curated for your family’s joy and wonder. The welcoming communities, with their cozy eateries and comfortable stays, wrap you in the genuine warmth of New England hospitality, making you feel right at home. 

Choosing the Berkshires for your family escape means stepping into a storybook of memorable experiences, where family bonds are celebrated and strengthened against unparalleled natural and cultural beauty.

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