Group Travel Articles

Dining With A Group Tastes Better in the Berkshires

By Lisa Green

There’s nothing that advances group bonding more than sharing meals, and the Berkshires offers a wealth of venues eager to feed your groups. The menus are superb, the locations ideal and the variety will suit almost any type of population you’re hosting.

Beginning with the northern reaches of the Berkshires, consider bringing your group to the ‘6 House Pub in Williamstown, which ushers group diners into The Publick Room. Formerly an old barn, this now-formal dining room filled with antiques, upholstered settees and a fireplace conveys the comforts of a beautifully furnished living room — a perfect complement to a meal before or after a tour of the nearby Clark Art Institute. In North Adams, the Freight Yard Pub welcomes guests in the private room upstairs or the patio. If guests finish their meals early, they often like to meander over to the visitors center at Western Gateway Heritage State Park to get a glimpse of the history of North Adams. The world-famous MASS MoCA is a short walk away, too.

A detour to the Yankee Candle Village in South Deerfield can work up an appetite. Fortunately, Chandler’s Restaurant is on site, providing tour operators a choice of the Wine Cellar lounge or Vineyard rooms, or box lunches for guests who’d like to take their meals out to the picnic tables on the grounds.

In central Berkshire County, the town of Pittsfield is a must-see and one of the must-dos is Baba Louie’s Pizza, which specializes in unique wood-fired pizzas and vegetarian and vegan options. It’s right in the middle of downtown, which allows for short walks to shopping, theater and movies.  In Lenox, The Gateways Inn welcomes tourists for lunch or dinner.  The elegant setting in this former mansion gives guests a chance to experience for themselves the luxury and grace that they will observe when they tour the Gilded Age mansions in town.

The quintessential New England town of Stockbridge has the bragging rights of The Red Lion Inn, which lives up to its reputation by serving New England-style menus in its lovably traditional dining room. The Red Lion’s kitchen can also provide box lunches for those who prefer to picnic on the grounds of Stockbridge’s other attractions, such as Chesterwood. (Added value: Tour operators will receive an information sheet about Stockbridge, and guests will receive a discount coupon to the inn’s gift shop.)

Closer to the south end of the county, the Route 7 Grill is known for its barbecue and New England favorites made from locally produced meats and produce. Your groups will also leave really happy after finishing the meal with Route 7 Grill’s chocolate cake before heading to the theater, Tanglewood or the many other activities that make the Berkshires a premier vacation destination. Bon appétit!

For a complete list of Berkshire restaurants click here.

Lisa Green is a freelance writer and advertising director of