Group Travel

Explore the Flavor of the Berkshires

Bring a group to the Red Lion Inn The Lion's Den for dinner and live musicIn a region known for its award-winning farm-to-table cuisine, it’s easy to find a restaurant serving inspired dishes made with fresh, local ingredients. From casual to fine dining, many establishments in the Berkshires and nearby Pioneer Valley welcome groups by offering creative menus designed to satisfy hungry travelers while highlighting the seasonal flavors of New England.

Here’s a sampling of the many dining options available during your visit with us:

If your itinerary brings you to Williamstown, home to the world-class art collections at The Clark or Williams College Art Museum, plan a meal at the Gala Steakhouse & Bistro at The Orchards Hotel. Creative comfort foods featuring farm-fresh ingredients capture the essence of the region. Add to the local flavor with a craft beer, cider, or seasonally inspired cocktail.

In nearby Hancock, John Harvard’s Brewery & Ale House at Jiminy Peak
serves American fare and award-winning craft beers. From pasta to burgers to seafood and soups, this New England brewpub has a distinct appeal. Relax and dig into a hearty meal and a pint after a day of outdoor adventure at Jiminy Peak Mountain Resort, or after exploring nearby Hancock Shaker Village.

In downtown Pittsfield, the central location of Hotel on North is popular with visitors to the city’s growing cultural district. This 45-room boutique hotel is part of the Main Street Hospitality Group that also owns the Red Lion Inn in Stockbridge. The award-winning chef for both is Brian Alberg, whose seasonal menus showcase high-quality foods grown and produced primarily in Massachusetts, Vermont, and the Hudson Valley. Private dining rooms are available in both locations. The Red Lion, especially welcoming for groups, has several dining options from casual to formal. Sample locally distilled spirits and microbrews. And experience some of the quirkiness of Hotel on North, where an antique birdcage elevator to the right of the bar is now in service as intimate seating for two.

For a more casual atmosphere in Pittsfield, check out J. Allen’s Clubhouse Grille. Pizza, burgers, sandwiches and homemade soups are just some of the pub fare made with ingredients produced or grown locally. The private dining room seats 40. Enjoy a quick and easy meal here before a show at the Colonial Theatre or Barrington Stage, or a day exploring the Smithsonian-affiliated Berkshire Museum.

Just south of downtown, Mazzeo’s Ristorante on Route 7 in Pittsfield offers a convenient location with ample parking and authentic fine Italian-American dining recognized among the best in western Massachusetts. With homemade sauces and pasta, and decadent desserts such as tiramisu and gelato made on the premises, this is truly a memorable meal. Mazzeo’s is also an event space, so seating and serving large groups is another specialty of the house.

For Pan-Asian cuisine with a Berkshire twist, bring your group to Enso Bistro in Pittsfield or Jae’s Asian Bistro in Lenox. Jae’s offers Korean specialties and a design-your-own dish option: choose the sauce, type of noodle or rice, and add chicken, beef, or shrimp. Enso emphasizes organic and natural foods, including the sushi rice. The tasteful décor adds to the upscale vibe.

Are you bringing your group to the Premium Outlets in Lee or on your way through town from I-90 to a destination further north? 51 Park Street Restaurant and Tavern has two private dining spaces that seat up to 60. Choose from their scrumptious selection of house made soups, stromboli and wood-fired pizzas, burgers, salads, and nibbles to customize a menu for your group. This is a convenient spot to rest and recharge with a delicious meal before getting back on the road.

Crissey Farm in Great Barrington is the place to bring a large group in south county. Adjacent to hotels and the Barrington Brewery, it’s just north of the downtown area on Route 7 with easy bus parking available behind the restaurant. Highly rated by Zagat’s, Frommer’s, AAA, and Bon Appetit, Crissey Farm welcomes groups of up to 200 in its airy dining space, with views of Monument Mountain to the north.

Just a short drive east from the Berkshires, you’ll find Historic Deerfield, in the Pioneer Valley. Rolling farmlands welcome you as you approach Champney’s Restaurant and Tavern at the Deerfield Inn. This landmark destination is a comfy respite after a day immersed in history at the museum or at any of the many cultural or shopping locations nearby. Groups, large and small, enjoy the farm-to-table dining and comfy accommodations.

When you bring your group to the Berkshires for our world-class art and culture, historical landmarks and outdoor recreation, expect a warm, friendly welcome steeped in New England’s unique traditions and hospitality. It’s an unforgettable adventure.