As someone who's spent 25 years writing about travel—and 10 of those living on the East Coast—I’ve wandered through the Berkshires more times than I can count. If you ever crave a place where rolling mountains meet art, culture, and incredible food, this is where I’d send you. You’ll get scenic views, charming historic towns, and a surprising number of things to do, no matter the season.
When I first discovered the Berkshires, I was living just a few hours away. You’ll find it tucked into the hills of Western Massachusetts, an easy getaway from New York City, Boston, or Albany. I always appreciated how close it was—and how quickly I could swap traffic for trees and galleries.
One of the things I love most? The variety. You might start your day exploring a museum, then head to a farm-to-table restaurant I still daydream about. If you're like me and need to stretch your legs, you’ll find trails, canopy tours, and biking routes that wind right into the hills. Come winter, I’ve skied here too—it’s a quiet gem for that.
Best Time to Visit
If you’re asking me, I’d say go between May and October. That’s when I find the region really shines. Fall foliage is something I’ve chased here more than once—absolutely worth it, but you’ll need to plan ahead. If you love winter, I’ve done romantic weekends here too, with snowy walks and cozy inns.
How to Get There
- By Car: I’ve always driven via the Massachusetts Turnpike (I-90). From Boston, it usually takes me 2.5 hours; from NYC, about 3.
- By Bus: If you’d rather not drive, you can take Peter Pan or Greyhound buses to towns like Pittsfield, Great Barrington, or Lenox. I’ve done it both ways, and each has its perks.
- By Train: You might like Amtrak’s Lake Shore Limited—it stops in Pittsfield and connects Boston and Albany. I’ve used it for relaxing, scenic trips.
Where to Stay
- Red Lion Inn in Stockbridge – I stayed here on my first trip, and I’ve returned more than once. You’ll love its old-world charm and the way it feels like stepping into a New England postcard.
Best Things to Do in the Berkshires
Monument Mountain Reservation - Hike scenic trails and admire sweeping views on an easy fall trip.
Hancock Shaker Village - Explore historic buildings and see farm animals on an affordable family outing.
Berkshire Botanical Garden - Walk among blooming flowers and discover native plants on a peaceful spring retreat.
Berkshire Museum - Visit interactive exhibits and explore local history on a fun trip with kids.
Bousquet Ski Area - Go skiing and enjoy snowy slopes on an exciting winter adventure.
Catamount Aerial Adventure Park - Climb rope courses and zip through trees on a thrilling summer trip.
Catamount Ski Area - Hit the slopes and savor mountain views on an exciting weekend getaway.
Chesterwood Museum - Admire sculpture gardens and explore the artist’s studio on an unusual cultural trip.
The Clark Art Institute - See world-class art and stroll peaceful grounds on a romantic couples escape.
In Summary...
(and if you want to revisit my photo journey)