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Family-Friendly Events in Berkshire County

Fall Foliage Children’s Races and Family Fair (October)
Held in conjunction with the Fall Foliage Parade, the Fall Foliage Children’s Races and Family Fair in North Adams is a highlight for families. Kids can compete in friendly races, enjoy carnival games, and partake in arts and crafts. The fair’s vibrant atmosphere and seasonal activities make it a must-attend event during autumn.

Berkshire Museum’s WeeMuse Adventures (Year-Round)
The Berkshire Museum’s WeeMuse Adventures program is a series of interactive, educational events designed for young children and their families. Held throughout the year, these programs combine art, science, and history through hands-on activities, story times, and exhibits. It’s a fantastic way to introduce children to the museum’s world of discovery.

Family Fridays at Pleasant Valley Wildlife Sanctuary (Summer)
Family Fridays at Pleasant Valley Wildlife Sanctuary offer families a chance to explore nature together. With guided hikes, wildlife observation, and nature-based crafts, these weekly events immerse kids in the beauty of the Berkshires’ natural environment. It’s a great way to spend a summer day learning about the outdoors.

The Great Barrington Holiday Stroll (December)
The Great Barrington Holiday Stroll is a festive event that brings families downtown for holiday-themed fun. Featuring a tree lighting ceremony, horse-drawn carriage rides, and visits with Santa, it’s the perfect way to kick off the holiday season. Local shops offer treats and specials, making it a cheerful community event for all ages.

Berkshire Botanical Garden’s Family Days (Seasonal)
The Berkshire Botanical Garden hosts Family Days throughout the year, featuring hands-on activities that connect children with nature. Families can engage in gardening workshops, nature walks, and craft sessions that promote environmental awareness and creativity. These events offer a wonderful opportunity for families to bond while exploring the beauty of the garden.

Stockbridge Summer Arts and Crafts Festival (August)
The Stockbridge Summer Arts and Crafts Festival is a vibrant event that showcases local artisans and provides a fun-filled day for families. Held annually in August, this festival includes interactive art activities, live music, and delicious food options. It’s the perfect setting for families to celebrate creativity and enjoy the artistic spirit of the Berkshires.

Winter Wonderland at Bousquet Mountain (December)
Winter Wonderland at Bousquet Mountain transforms the ski area into a festive holiday experience for families. This December event includes winter sports, snow tubing, and holiday activities like ice skating and visits with Santa. It’s a magical way for families to embrace the winter season and create cherished holiday traditions together.

Lee Founder’s Weekend (September 28-29)
Lee Founder’s Weekend is a lively celebration of the town’s rich history and community spirit. This annual event features a variety of activities, including historical reenactments, guided tours of local landmarks, live music, and family-friendly games. Attendees can enjoy delicious food from local vendors while learning about the fascinating stories that shaped Lee. It’s a perfect opportunity for families to connect with their heritage and celebrate the vibrant community in the Berkshires.

Haunted Hancock Tour (October)
The Haunted Hancock Tour invites brave souls to explore the eerie history of Hancock, Massachusetts, under the cover of darkness. This guided walking tour delves into the town’s spooky past, highlighting ghost stories and local legends that have haunted its historic sites. Participants will wander through the shadowy streets and learn about the fascinating tales of the people who once called Hancock home. Perfect for families and thrill-seekers alike, this event promises a spine-chilling adventure that combines history, mystery, and a touch of Halloween spirit.

Hawthorne Valley Farm Fall Festival (October)
Hawthorne Valley Farm Fall Festival is a delightful celebration of the harvest season, inviting families to enjoy a day filled with fun and festivities. This annual event features hayrides, pumpkin picking, live music, and delicious farm-fresh food. Visitors can participate in workshops, explore the farm's beautiful grounds, and learn about sustainable agriculture practices. It’s a perfect opportunity for families to connect with nature and enjoy the vibrant autumn atmosphere in the Berkshires.