Off Season Escape: Things to Do in Stockbridge, MA

Blue Steps at Stockbridge, MA

On a crisp morning not too long ago, I walked out the front door of my room at the Red Lion Inn just off Main Street and headed in the direction of a forest, where in 10 minutes I’d be hiking along the Housatonic River.

It seemed like a wild idea, exploring the area so freely without four wheels. I was in a small town called Stockbridge in the middle of the Berkshires, a place that had long epitomized car-dependency. My parents had raised me on stories of adventure, including those 1970s Charlemont road trips to a perfect cabin in the woods. I had envisioned their car (I think it was a Volvo station wagon), regularly stocked with wine, beef, and friends, as the way to escape city life. Taking a car never seemed like anything but the only option to get to the Berkshires.

The truth is, I never bothered to investigate. So on that crisp morning, easily-accessible-by-bus-Stockbridge felt like a secret I was slowly uncovering one step, and later, one pedal stroke at a time.

exploring the berkshiresStockbridge could fit in a snow globe, and feels like a second home after one weekend of wandering through it. The nearby attractions you’ll see in brochures, like the Norman Rockwell Museum, Berkshire Theatre Festival, Schantz Galleries and the Berkshire Botanical Garden, merit a visit. But if you want to slip into the local rhythm here in Western Massachusetts, you’d do best to take small bites, have a Bloody Mary in a rocking chair on the Red Lion Inn’s porch, then find a way to get lost—though not necessarily in that order.

You might start with a Berkshire Apple Pancake one morning at The Red Lion Inn’s main dining room, and have breakfast at No. 6 Depot the next. Pop into Nejaime’s Stockbridge Wine Cellar to grab Zabars-quality picnic fixings for now and a bottle of something for later. After dinner at Once Upon a Table, you could go for a dip in the Inn’s outdoor Jacuzzi or end your nights below your bed at The Lion’s Den, tapping your toes to live country blues or acoustic folk.

In between sun up and sun down, seek out the kind of peace and quiet that’s hard to come by in New York City. Small town sounds are heartwarming, especially during the holidays, but just for a bit, venture away from the bell-ringing boutique doors, chipper shopkeepers, and soles crunching over leafy sidewalks. Make a right off Park Street, pass under a stoned arch and over a bridge. Go left along a flat path that parallels plant-covered train tracks and the babbling river. Head back towards the bridge and go left across the train tracks. Walk deeper into the woods along 1.4-mile Ice Glen Trail, where Nathaniel Hawthorne often hiked, and revel in the glacial ravines, mossy boulders, and hemlocks that make up this dramatic Hobbit-inhabited landscape.

Cyclists will wish they could bike over the George Washington Bridge and find themselves in the Berkshires. But the beautiful, undulating roads alone are worth a visit, and Stockbridge is a great starting point for two-wheeled travelers of any fitness level. If you’re interested in a longer distance with some elevation, have a Felt F6 delivered to the Red Lion Inn by Berkshire Bike and Board ($35/4 hours or $50/24 hours, helmets included) and follow this route. The course will reveal Stockbridge Bowl, the Kripalu Center for Yoga & Health, countless farms, scenic overlooks, and few cars. Halfway through this 22-mile ride, you’ll brake at Bartlett’s Apple Orchard for cider donuts that will keep you warm and energized for a while. You’ll wind your way back to the Red Lion Inn, ready for a drink by the fire with Simon, a cat and Lobby Ambassador in residence.

Red Lion Inn stockbridgeAlthough the Red Lion Inn’s Peter Pan bus package has ended, the ride up is a breeze and the bus drops you right off in front of the Inn, almost like a chauffeur.

The Red Lion Inn has hosted six presidents, John Wayne, and Bob Dylan, and is a “living, moving museum,” says marketing and communications manager Stephanie Gravalese-Wood. She recommends exploring the halls on various floors that are filled with fascinating pieces of history and an impressive range of art, from Norman Rockwell prints to the owner’s own quirky collection. In the off season, the cozy, colonial-styled rooms in the Main Inn, guest houses and newly opened Maple Glen rooms start at $105/weekday and $125/weekend.

How to get there: The scenic bus ride takes less than four hours and costs $80/adult roundtrip ticket or $48/child. Peter Pan departs from Port Authority. To learn about special packages or to plan a holiday getaway, visit For information on local seasonal events, visit For a snack on the ride home, pick up some Berkshire-made BOLA granola in the Red Lion Inn gift shop.

Photos: Massachusetts Office of Travel & Tourism, wseltzer, wo1vesrx, Timothy Valentine, Lauren Matison, Red Lion Inn