Group Travel Articles

Inspiration for Planning a Summer Tour to the Berkshires

Groups have long enjoyed coming to the Berkshires in our summer season. Whether it has been for the vibrant cultural scene, the great outdoors, the spa scene, or for an itinerary chocked full of visits to our world-class museums. Here’s a list of 20 not to miss events and attractions happening in the Berkshires this summer, we hope it will motivate you to bring a group this summer or use this as inspiration to plan an upcoming tour to our region.


TanglewoodLenoxThe summer home of the Boston Symphony Orchestra welcomes conductor Andris Nelsons in his inaugural season and celebrates the 75th year of the Tanglewood Music Center. This year’s festival features returning favorites (Joshua Bell, Yo-Yo Ma, Emanuel Ax, Mark Morris), special events (A Prairie Home Companion with Garrison Keillor, Film Night with John Williams), and the Tanglewood debut of Lady Gaga and the Cirque de Symphonie. Lectures, tours, Saturday morning open rehearsals, and beautiful grounds are all at your finger tips. Don’t forget to pack a picnic!

Jacob’s Pillow Dance Festival, Becket. One of America’s oldest and preeminent dance festivals presents jazz, tap, ballet, and contemporary performances in a magical wooded setting. Among this year’s highlights, NPR’s Ira Glass stars in Three Acts, Two Dancers, One Radio Host and a celebration of the 90th anniversary of the Martha Graham Dance Company with a world premiere by choreographer Mats Ek. Free Inside/Out performances Wednesdays–Saturdays on the outdoor stage.

Shakespeare & Company, Lenox. Founded by Tina Packer, this critically acclaimed company presents Shakespeare’s Henry V, Comedy of Errors, and Hamlet this season along with new plays and special events. The free Outdoor Banks Festival is popular with families.

Williamstown Theatre FestivalWilliamstownTony Award-winning plays, workshops, readings, and late-night cabarets. Kyra Sedgwick opens this year’s festival June 30 in the world premiere of Off the Main Road. 

Berkshire Theatre Group, Pittsfield and Stockbridge. Karen Allen directs Frankie & Johnny in the Clair du Lune and Aaron Mark directs Deathtrap on the Main Stage in Stockbridge. At the historic Colonial this summer: Comedian Robert Kline and Mary Poppins.

Barrington Stage Company, Pittsfield. Musicals, theater, comedy, new works, and cabaret shows in downtown Pittsfield. The Main stage season opens June 10 with Man of La Mancha. Bring the kids for Shrek the Musical, July 22–August 9. 

Berkshire Crafts Fair, Great BarringtonThis juried show attracts more than 90 fine artists from around the country. High-quality jewelry, leather, pottery, fiber, furniture, metalwork, and more. August 14–16.


Hancock Shaker Village, Hancock. This living museum has a working farm with live animals, nature trails, herb and flower gardens, and an extensive collection of Shaker furniture. The architectural and engineering ingenuity of the Shakers is evident in the Round Barn and more than 20 buildings open for tours, demonstrations, and lectures. Café and Scoop ice cream shop are open daily for lunch and snacks.

Norman Rockwell Museum, Stockbridge. Illustrator Norman Rockwell lived in Stockbridge and often used local residents of the Berkshires as models for his paintings and Saturday Evening Post covers. His original work and art studio are on view here along with visiting exhibits. An installation by New Yorker cartoonist Roz Chast runs June 6–October 26. 

Sterling and Francine Clark Art Institute, WilliamstownIn addition to its vast collection of master works, the Clark presents two very special exhibitions this summer: Van Gogh and Nature, June 14–September 13, and James McNeill Whistler opening July 4th featuring the only East coast appearance of his famed painting, Whistler’s Mother. 

MASS MoCANorth AdamsIn a repurposed brick mill building complex, MASS MoCA presents ongoing and visiting contemporary art installations, live music events including the fifth year of the three-day Wilco Solid Sound festival in June, and activities and workshops for kids and adults. The Lickety Split Café serves lunch, ice cream, and snacks. 


Arrowhead, Home of Herman Melville, Pittsfield. At a simple writing desk in an upstairs room with a view facing north toward Mt. Greylock, Herman Melville found inspiration for the great white whale he called Moby-Dick. The Melville homestead is now a museum and working farm with goats and heritage breed chickens, including a speckled Sussex rooster named Herman. 

The Mount, Edith Wharton’s Home, Lenox. Visitors can take daily tours of the house and gardens as well as specialty-theme tours including a look at servant’s life, an evening ghost tour, and walk through the outdoor sculpture show. Enjoy live jazz on the terrace, Friday and Saturday nights in July and August. 

Naumkeag, Stockbridge. The 44-room Gilded Age summer retreat of Joseph and Mabel Choate has panoramic views facing Monument Mountain and expansive terraced gardens designed by Fletcher Steele. Be sure to check out all their Naumkeag at Night activities, great for the whole family. 

Chesterwood, Stockbridge. Noted Lincoln Memorial sculptor Daniel Chester French lived and worked on this spacious country estate. Don’t miss their Sunday evening music festival called Chesterfest. You can book an overnight stay in French’s Meadowlark studio, located on the property and managed by the Red Lion Inn 

Bidwell House Museum, Monterey. Marking 25 years of welcoming visitors to the Berkshires’ this 1750s house sits on 192 acres of fields, gardens and forest and tells the story of the early settlement of the Berkshires. It was the home of the Reverend Adonijah Bidwell, first pastor to the pioneer community. 


Ramblewild, Lanesborough. Climb, traverse, and zipline tree-to-tree in a series of challenging obstacle courses that weaves through 10-acres of a pristine hemlock forest. 

Mt. Greylock State Reservation and Bascom LodgeAdamsExplore hiking trails, camping, the Veterans War Memorial Tower, and a breathtaking view of three states from the highest peak in Massachusetts. Bascom Lodge at the summit offers food, lodging, and special events in season. Accessible by car or on foot. 

Trustees of Reservations. Dedicated to the preservation and conservation of more than 100 natural and historical landmarks in Massachusetts, the Trustees steward nature trails and education centers at Bartholomew’s Cobble in Ashley Falls, Monument Mountain in Great Barrington, and Pleasant Valley Wildlife Sanctuary in Lenox.

Berkshire Natural Resource Council A non-profit land conservation organization working throughout the Berkshires in Massachusetts to preserve threatened lands but also working on accessibility to all that the Berkshire outdoors has to offer. Be sure to check out their event calendar as they offer a great variety of guided hikes all summer long at a variety of experience levels.

Want more ideas for your Berkshire itinerary then go here. There’s something for everyone!