Berkshire County Family Bucket List: Must-Do Experiences, North to South
Planning a family getaway in Western Massachusetts? With mountain views, charming towns, cultural attractions, and four-season adventure, the Berkshires easily rank among the best family vacation spots in New England. Whether you’re visiting in summer sunshine or fresh winter snow, there’s no shortage of memorable things to do in the Berkshires.
Here’s your north-to-south guide to the ultimate Berkshire County family bucket list.
North County Adventures: Williamstown & North Adams
Northern Berkshire County blends art, nature, and outdoor adventure year-round.
Explore Art & Creativity
Start at the Clark Art Institute, where world-class art meets scenic walking trails. It’s ideal for families who want a mix of culture and fresh air.
In nearby North Adams, MASS MoCA offers immersive, large-scale exhibits that feel interactive and engaging — be sure to check out MASS MoCA Kidspace for ongoing programing and events.
Hit the Slopes at Jiminy Peak
Winter transforms the Berkshires into a snowy playground. Jiminy Peak Mountain Resort is one of the most popular ski destinations in Massachusetts, offering lessons, tubing, and terrain suitable for beginners through advanced skiers. It’s one of the top family-friendly vacation spots for snow lovers.
For smaller skiers or families new to the sport, lessons and gentle beginner areas make skiing one of the most exciting toddler-friendly activities during winter visits.
Mount Greylock in Every Season
Drive or hike up Mount Greylock in warmer months for sweeping views. In winter, adventurous families can try snowshoeing or cross-country skiing on designated trails — unforgettable family activities Berkshire County offers when snow blankets the mountains.
Central Berkshires: Pittsfield, Lenox & Lee
The heart of the county offers lakes, live performances, and winter recreation.
Discover the Berkshire Museum
The Berkshire Museum is perfect for colder days, with hands-on exhibits, an aquarium, and interactive science displays. It’s a reliable indoor option when you’re searching for winter things to do in the Berkshires.
Bousquet Mountain & Winter Sports
Head to Bousquet Mountain for skiing, snowboarding, and tubing. Its manageable size and family-friendly atmosphere make it ideal for beginners and younger children learning the ropes.
Prefer a slower pace? Try sledding at local hills or cross-country skiing at Kennedy Park in Lenox — simple, affordable kid friendly activities that make the most of snowy days.
Summer at Tanglewood
When the snow melts, families can spread out on the lawn at Tanglewood for live performances. It’s a cultural experience that still feels relaxed and accessible for families.
South County Escapes: Great Barrington & Sheffield
Southern Berkshire County shines in every season.
Ski Butternut
Ski Butternut is a local favorite for approachable terrain, excellent ski schools, and tubing lanes. It’s especially popular for families with younger children, making it one of the best winter family-friendly vacation spots in the region.
Ride the Rails
Train enthusiasts will love the Berkshire Scenic Railway Museum. Seasonal train rides offer a unique way to experience Berkshire County — a charming addition to your list of Family activities Berkshire County.
Farms, Trails & Outdoor Play
Warmer months bring berry picking, farm visits, and easy hikes like those at Bartholomew’s Cobble. These hands-on experiences remain classic toddler-friendly activities and memorable outdoor adventures.
Why the Berkshires Are a Four-Season Family Favorite
What truly makes this region one of the best family vacation spots is its year-round appeal. Summer offers lakes, hiking, and cultural festivals. Fall brings vibrant foliage and harvest fun. Winter invites families to ski, snowshoe, and sled. Spring awakens trails and farm experiences.
From north to south, you’ll find diverse family-friendly vacation spots and endless things to do in the Berkshires, no matter the season. Whether you’re planning a snowy ski weekend or a sunny summer escape, Berkshire County delivers adventure, charm, and unforgettable family memories.
Stay at Porches Inn
Porches Inn is the perfect home base for your family adventure in the Berkshires—book stay today!
