Where to Stay and Play in the Berkshires

Massachusetts has plenty of beautiful spots perfect for a family vacay, but the Berkshires in Western Massachusetts has a certain something that can’t be ignored. This hilly region is a skiing haven during the winter months, but during the rest of the seasons, this beautiful destination has so much adventure for families, you might find it hard to decide where to begin.

Outdoor adventure is waiting around every corner, with miles of hiking and biking trails and woods that seem to stretch on forever. The Chester-Blandford State Forest, located outside the town of Chester, offers trails for all skill levels. One trail takes you to Sanderson Falls.

There is also a 90-mile portion of the Appalachian Trail running through the region where you can spend a few hours or a whole day hiking this epic trail woven into the country’s history. One of the easiest places to access the trail in the Berkshires is at Mount Greylock, where you can enjoy a hike filled with beautiful scenic views of the area (and the trail is dog-friendly, too).

If you want to get out of the heat of the summer sun, the Berkshires has incredible museums and gardens to explore. The Clark Art Institute in Williamstown is home to an incredible collection of artwork from around the world, while Eric Carle Museum of Picture Book Art in Amherst lets children explore the artistry behind some of their favorite picture books — and adults can enjoy some whimsical nostalgia from the stories we grew up with.

The Naumkeag House and Gardens in Stockbridge is an ideal place to experience a touch of the Gilded Age with a 44-room mansion from the late 1800s. This mansion is surrounded by beautiful, ornate public gardens. The Berkshire Botanical Gardens, also in Stockbridge, let you continue your outdoor explorations as you make your way through 23 different seasonal gardens and exhibits.

You’ll find no shortage of great places to stay in the Berkshires, but if you are looking for something that is quintessential New England, you’ll want to check out one of the many bed and breakfasts or charming inns that dot the region. The Williams Inn in Williamstown provides a place of peaceful luxury that perfectly blends elegance with a rustic twist in a location that puts you in the heart of the Berkshires, so you can easily access everything the region has to offer.

(Insider tip: With so many great places to explore, you’ll want to rent a car to get around during your stay. Ride shares like Uber and Lyft are not consistently available everywhere throughout the Berkshires.)