Stay & Play
Happy Trails: Adventure Awaits
Discover the Rich Culture of Berkshire County (The Way Locals Live It)
Berkshire County, tucked into the cozy corners of western Massachusetts, isn’t just a scenic backdrop for your next Instagram post—it’s a full-blown vibe. With tree-covered trails, glassy lakes, and waterfalls that look like nature’s top stylist designed them, this place is paradise for anyone who knows their way around a pair of hiking boots or a picnic blanket.
But here’s the real kicker: the Berkshires are as culturally stacked as they are photogenic. We’re talking world-class art museums, indie theater gems, and a calendar full of local events that’ll have you casually name-dropping venues like Mass MoCA and the Clark like you’ve been coming here for years.
Backpacking Trips
Where the Wild Things Are
Monument Mountain: A Literary Legend
Embark on a 3.5-mile round-trip hike up Monument Mountain, where literary giants like Herman Melville and Nathaniel Hawthorne once roamed. The summit offers panoramic views of the Housatonic River Valley and the Catskill Mountains. It’s a moderate trek that rewards you with a slice of history and breathtaking scenery.
Water Sports
Paddle, Play, and Make Memories
Dive into adventure at Stockbridge Bowl, a Berkshires summer hotspot — perfect for kayaking, standup paddleboarding (SUP), fishing, and cruising in a motorboat. Home to the Cookie Bowl, Chocolate Bowl, and the Josh Billings RunAground Triathlon, it’s where fun meets friendly competition. Chill, race, or just float — this lake’s got it all!
Family Hiking Trips
A Trail for the whole Family
Cascades Waterfall: Instant Pool
Tucked away in North Adams, just a short stroll from Brayton Elementary, this hidden gem is a great summer escape. The trail’s a breeze, but it’s the payoff that counts! You’ll be rewarded with an awesome view and a natural pool perfect for a chill dip to beat the heat, this spot’s got you covered. You’ve gotta check it out!
Winter Sports
Snow Much Fun
Bousquet Mountain skiing with a side of history in Pittsfield is a popular destination. It was the first ski area in the Berkshires and the country to offer night skiing. It all happened back in 1936 with the help of General Electric. It’s got 23 trails and a terrain park, making it a great spot for skiers of all levels, and perfect for families looking to hit the slopes.