Group Travel

The City of Pittsfield is a Four Season Group Destination

The City of Pittsfield is the vibrant, lively hub of the Berkshires, featuring stellar group tour attractions and central access to the whole county. Your group can enjoy four-season entertainment and fun, from Tony Award-winning theatre and lively festivals to living history museums like Hancock Shaker Village, where your group can also enjoy a traditional Shaker meal or a casual lunch, and Arrowhead, Herman Melville’s historic home where he wrote the classic Moby Dick. All nestled in the verdant hills of the Berkshires!

Enjoy year round outdoor recreation at Bousquet – a ski area in the winter and family fun center in the summer. The city also features the easy-to-explore Canoe Meadows Audubon Sanctuary, Pittsfield State Forest, and two beautiful lakes all within city limits.

Downtown Pittsfield is home to the Upstreet Cultural District, the first official cultural district west of Boston and the only one in the Berkshires. The compact, walkable Upstreet Cultural District features two historic districts, distinctive architecture and public art, over forty artist studios, including 17 studios at group tour friendly NUArts Studios & Gallery, the Berkshire Museum, the Berkshire Theatre Group’s Colonial Theatre, Barrington Stage Company’s two theatres and cabaret, the Lichtenstein Center for the Arts, and many more cultural attractions.

The Upstreet Cultural District also features over fifty restaurants for all tastes and price ranges, including group tour friendly Spice Dragon, while Mazzeo’s Ristorante, bordering Lenox offers authentic Italian food for groups.

Pittsfield is home to dozens of unique shops and boutiques, including outlet shops for local companies that offer wholesale prices to bargain shoppers. The Pine Cone Hill Outlet Store offers gorgeous heavily discounted home goods, Museum Facsimiles Outlet Store, sells frames hand silkscreened and letterpress cards created right here in Pittsfield, and Ancient Language boutique sells exquisite locally made yoga and casual wear.

If your group would like a hands on arts experience while visiting the creative Berkshires, come to Bisque, Beds and Beyond in Pittsfield’s Upstreet Cultural District, where owner Donna Todd-Rivers will provide custom-designed classes in ceramics, fused glass, beading and more, giving your participants a one-of-a-kind handmade treasure to return home with. Groups with an interest in visual arts will enjoy the year-round First Fridays Artswalk in Pittsfield’s Upstreet Cultural District, featuring dozens of local and regional artists on display in over 20 downtown locations.

Pittsfield features unique and lively festivals and special events year-round. In the winter, the 10X10 Upstreet Arts Festival features over 50 different performances and events in February. The Baby Animals celebration at Hancock Shaker Village is a Berkshires spring tradition in April, while May brings 3rd Thursdays, a monthly cultural street festival in downtown Pittsfield that features four stages of music, street performances, vendors and more every month through October.

Summer special events include the Berkshire International Film Festival in early June; and Pittsfield’s festive Fourth of July Parade, one of the largest in New England. In July your groups can enjoy the annual Pittsfield Garden Tour, Polish Family Picnic, or the Pittsfield City Hoopla, an outdoor hula hoop festival. August brings the Pittsfield Ethnic Fair & Car Show in Pittsfield’s Upstreet Cultural District, followed by the WordXWord Festival, celebrating words spoken, written and sung; and the Greek Fest.

In the fall, enjoy the Berkshires spectacular autumn foliage along with the Country Fair at Hancock Shaker Village in September, celebrating the bounty of the harvest with agricultural demonstrations, wagon rides, a fabulous Farmers Market, and our huge tents full of the best local and regional crafters and artisans. The annual Pittsfield CityJazz Festival follows in October, featuring great jazz musicians both local and international. In November and December the galleries of the Berkshire Museum come alive with dozens and dozens of imaginatively decorated trees in the Festival of Trees. December also features a glorious production of A Christmas Carol at the Gilded Age Colonial Theatre, as well as the Handmade Holiday Festival, featuring the best local and regional artisans for unique holiday shopping.

And winter, spring, summer or fall, you’re a short drive away to everything else the Berkshires have to offer!


For more information about group tour opportunities in Pittsfield, the hub of the Berkshires, contact the Pittsfield Tourism Commission at 413-499-9348, [email protected] or visit