What to Do Off the Slopes

By Francesca Shanks

The Berkshires and Southern Vermont just do winter right. We’ve got years of experience, after all — plenty of time to fine-tune the ratio of ingredients in our Hot Toddies and determine the exact number of layers we’ll need to transition from the slopes to a relaxing dinner lit by wood fireplace.

If you’re visiting the area to ski or snowboard, the best course of action for finding food, drink or other attractions is to ask a local. Whether you’re here for a budget ski day or a luxurious long weekend, options abound.

Darcie Sosa, a freelance writer, Berkshire native and marketing manager at Berkshire South Regional Community Center in Great Barrington, Mass., is fond of Thistle and Mirth in Pittsfield, Mass., for a drink or light meal.

“I feel like I can go there and have a drink and a real conversation,” she said. “There are no televisions, (usually) no loud music, and [there are] friendly staff and patrons.”
If you want something a bit more gilded, Sosa says try Methuselah Bar and Lounge in Pittsfield, or Mezze in Williamstown, Mass. — both about equidistant from Jiminy Peak in Hancock, Mass.

“Both have cocktail experts working their bar, and both have delicious food and a really beautiful environment.”

As a bonus, Mezze focuses on local ingredients, so whatever you eat there will be truly unique. Methuselah has a friendly, accessible tapas menu, which you can eat while seated at a comfy couch or cozy booth.

For those craving something on the sweeter side, Sosa says Chocolate Springs in Lenox, Mass., is her pick for best hot chocolate in the Berkshires.

Hotel on North in Pittsfield, run by Main Street Hospitality Group, is a very good landing spot after a day of skiing. The hotel offers special ski packages that include lift tickets to Jiminy, and has recently built a ski locker area close to its parking lot so you can load in and out easily.

“This year, we really wanted to make it as ski-friendly as we could,” said Paul Clark, general manager of Hotel on North and Eat on North, the hotel’s restaurant and bar hot spot.

Eat on North is consistently rated high and offers a spacious bar as well as a dining area. The restaurant’s ex-White House chef Ron Reda plans theme menu nights (think oysters or taco evenings) as well as traditional, hearty dinner offerings.

Craft bar in Bennington

With easy access to several great ski spots, Bennington, Vt., is hitting a new stride in terms of food and drink. Want something rustic, historic and quirky?

John Shanahan, executive director of the Better Bennington Corp., recommends the Tap House at Catamount Glass, a craft bar housed in the front room of the notable glassware factory.

Most of the tap house’s drink offerings are local to Vermont, and it’s right across the street from the iconic Bennington Potters.

“It’s turned into a very popular place, and it has an urban feel,” Shanahan said.
Expect to find the place bustling on a weekend — sometimes you’ll be able to catch a live band as well.

A beautiful drink from the martini bar at the Safford Mills Inn in Bennington, Vt. Photo by Caroline B. Snyder.

If you’re looking for a stiff drink (and perhaps a good Instagram photo background), Shanahan recommends Safford Mills Inn in Bennington, which boasts a martini bar and tapas options in a beautifully renovated front room.

“It’s cozy, beautiful, very warm, and very popular,” Shanahan said. “The perfect place to go after skiing.”

Good bets in Brattleboro

If you’re in Windham County, head to Brattleboro, Vt., for a quintessential New England small-city experience.

For a quick baked good or lunch, Amy’s Bakery Arts Cafe offers a casual dining area with picture windows and a striking view of the Connecticut River.

If you’re heading to or from the slopes on Route 91, The Marina on Putney Road has hearty meals to fuel up and a nice bar and apps to wind down. It, too, offers great views of the Connecticut River.

Romance off the slopes

Just want to cuddle up with your honey for dinner, a drink or a snack? Don’t worry, we’ve got you covered with a few good suggestions.

The Berkshires:

Eat a gorgeous meal nestled in the woods at John Andrews Farmhouse Restaurant in South Egremont, which keeps a wood fireplace burning all winter. Reservations: johnandrewsrestaurant.com, 413-528-3469

See live music and relax in dewy darkness at the Down County Social Club in Sheffield, below the Stage Coach Tavern. “It’s dark, intimate, and full of great musicians and vintage furniture,” says Darcie Sosa. Reservations: stagecoachtavern.net, 413-717-7476

Relax by the fire at the ’6 House Pub in Williamstown, or nestle into one of the wing-backed chairs in the common room. Full dinner menu. Reservations: 6housepub.com, 413-458-1896


The Harvest Brewing Co. in Bennington is about as local as you can get, with member-brewed beer on tap and lots of comfy seating. “They only play vinyl there,” says John Shanahan. “It’s a very cool spot.” Information: (802) 681-8520

Peter Havens Restaurant in Brattleboro shows up on lots of best-of Windham County restaurant lists. It’s an intimate spot with 10 tables and a bar. Reservations: peterhavens.com, (802) 257-3333

Eat “elegant, creative cuisine with a seafood focus and a French touch” (their own words) in a renovated dairy barn at Chantecleer Restaurant in East Dorset. Yes, Virginia, there is a stone fireplace. Reservations: chantecleerrestaurant.com, 802-362-1616.

Vermont Country magazine

Vermont Country has a hyperlocal focus on the Green Mountain lifestyle, its personalities, events, attractions and culture. The magazine appears six times a year, designed to complement the state and four-season living. VtCo magazine is a Southern Vermont publication of Vermont News & Media.

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