No matter the size of your group who doesn’t love relaxing together at the end of a busy day in a cozy locale that serves up delicious food and drink? The Berkshires has long been a culinary destination and we continue to enjoy sharing our love of local flavors with all of our visitors. Here are a few spots that would be the perfect addition to your Berkshire itinerary.
The sign in front of Firefly Gastropub & Catering in Lenox says it best: “eat, drink, laugh…lounge.” Inside the newly renovated Firefly, cozy couch-style seating and a glowing fireplace offer a warm, welcoming vibe. The long mahogany bar curving through the center of the space offers the perfect setting for conviviality and casual conversation. Bartender Billy Jack Paul, who Firefly owner Laura Shack refers to as ‘one of the best mixologists in the Berkshires,’ serves up craft cocktails, craft beers, and an extensive selection of wines.
In this location since 1993, Shack has reinvented the restaurant and its menu a few times to serve the needs of her customers, who are a mix of visitors and locals. The new gastropub fare includes noshes, small bites and enticing entrees made with farm-fresh Berkshire produce, house-smoked meats, and zesty house sauces. You’ll find familiar favorites here, with a flavorful twist. The signature Shack Caesar Off the Grill, for example, features lettuce and fresh croutons grilled right alongside the chicken. With its hugely popular half-price burger night, the kitchen now serving until 11 pm, and a growing calendar of live entertainment, Firefly continues to be a regular stop for good fun and great food; offering up a private room that is great for groups.
Laura Shack is also co-owner of 20 Railroad Public House in Great Barrington with business partner Ben Downing. Formerly known as 20 Railroad, or ‘20’, the restaurant’s recently renovated interior retains the iconic open-brick décor and a sturdy 28-foot mahogany bar of its predecessor. With the change in ownership comes a turn of focus toward eating local, responsible, and sustainable. Ingredients spotlight Berkshire farms, artisanal foods and locally roasted coffee, craft beers, and distilled spirits. With details such as house-ground and cured meats, hand-cut fries and house-made sodas, 20 Railroad Public House is quickly gaining a following and creating a history of its own.
When it comes to history, the Widow Bingham Tavern at the Red Lion Inn in Stockbridge and the ‘6 House Pub & Tavern at the 1896 House Country Inn and Motel in Williamstown are two of the Berkshire’s most notable landmark eateries offering that cozy feel you might be looking for as cooler weather settles into the Berkshires. While each is unique, both offer the tastes of the Berkshires and the comfort and hospitality you’d expect from their place in a classic New England inn.
At Widow Bingham’s, Chef Brian Alberg brings his strong support of Berkshire farmers to the table with delicious soups, salads, sandwiches, and grass-fed burgers served alongside local craft brews and spirits. The atmosphere is rustic with dark woods, exposed beams, creaky floors, and walls covered with historic images and signs from the area’s history. Be sure the group has time to explore the Inn too and pop into the gift shop.
The ‘6 House Pub offers homemade comfort foods and traditional pub fare in a scenic, relaxed setting. Co-owner and innkeeper Michael Oring, who bought the property in 2014 with his wife Carrie, says karaoke and open mic nights at ‘6 House are popular with locals as well as guests of the hotel. The feeling in the air is fun, and even a little quirky, he says, overseen by Harold, a bulls’ head mounted on the pub’s wall that has a bell around his neck. “Ring that bell”, says Oring, “and you’ve just bought everyone a round of drinks!”
Speaking of popular local watering holes, the Freight Yard Pub in North Adams has also long been a “go to spot” for locals and visitors alike. Upstairs they are able to host large and small groups in a private setting. Here you will feel like everyone knows your name and you will be able to enjoy one of the tastiest burgers in the region.
At the heart of the Berkshires in Pittsfield, you’ll find a small, but upscale place to grab a drink and some great food at Eat on North. Hotel on North’s resident bar has many local brews, delicious mixed drinks, and even an oyster bar that is often manned by local chef friends from around The Berkshires. Call in advance to get their private space in the dining room for your group or set up a special menu.
Nancy Macy is a freelance writer and editor based in the Berkshires.