Group Travel Articles

Is Your Group Ready? Here are Twenty Ways to Make the Most of a Berkshire Experience

Every summer we’re reminded how difficult it is to corral all the Berkshires has to offer into one cohesive list. It’s almost not possible, we like to brag, but here’s our valiant effort to help you plan groups itinerary and make sure that it is chock full of our summer must-sees and dos.

  1. Tanglewood. It’s the big Kahuna of all the festivals in the region, in terms of world recognition, programming and acreage. Summer home of the Boston Symphony Orchestra, its lineup includes classical music (Yo-Yo Ma, Gil Shaham, Emanuel Ax); jazz, folk and rock (Esperanza Spalding, Joan Baez, Jackson Browne), special events (A Prairie Home Companion with Garrison Keillor), lectures, open rehearsals and so much more…not to mention the most elaborate pre-concert picnics on the lawn. Super group friendly and great for a multigenerational group.
  2. Berkshire International Film Festival. Seventy films from 15 countries in four days, with locations in two towns (Great Barrington and Pittsfield): no wonder BIFF is one of the most anticipated events each year by residents and visitors alike. Cinema fans not only get their fill of soon-to-be-released movies, they get to rub shoulders with visiting directors and actors. This year, BIFF hosts Tony Shalhoub, Darlene Love, Mary Kay Place, Karen Allen, Chris Noth, Peter Riegert and others. Have film buffs who want to plan a tour, this annual event should be on their itinerary!
  3. The Mahaiwe Performing Arts Center . Formerly a vaudeville hall, The Mahaiwe in Great Barrington has been restored to magnificence, making it a magical place to see music, dance, films and special events. On stage this summer: Natalie Merchant with the Hudson Valley Philharmonic, Manhattan Transfer, Pink Martinii and Boston’s Early Music Festival. This venues offers year round programming so even if your group can’t make it in the summer, be sure to add one of their performances to your list.
  4. Shakespeare & Company. Celebrating its 35th season in Lenox, Shakespeare & Co. presents Love’s Labour’s Lost and Richard II, and brings back Olympia Dukakis for a second season, this year in Mother Courage and Her Children. But there’s so much more: discussions with actors, directors, designers and bestselling authors, and talkbacks after selected shows. Great spot for your group to grab a matinee regardless of the time of year.
  5. Barrington Stage Company. If you like full-fledged musical theater, intimate plays and American premieres, Barrington Stage in Pittsfield is your scene. The season gets underway with Leonard Bernstein’s jazzy On the Town and introduces Bashir Lazhar to the American stage. Other productions to consider: The Chosen, Much Ado About Nothing, and for the kids, The Little Mermaid. Perfect addition to a Berkshire itinerary that is focused on performing arts.
  6. Berkshire Theatre Group. The Berkshire Theatre Festival and the Colonial Theatre joined forces in 2011, and the resulting Berkshire Theatre Group has five stages on which to present theater, dance, music and entertainment in Pittsfield and Stockbridge. On tap this summer: Audra McDonald; Jane Atkinson and Treat Williams in The Lion in Winter, a production of Extremities directed by everyone’s favorite local star, Karen Allen, and so much more. With a variety of stages and shows there is sure to be something for everyone in your group.
  7. Jacob’s Pillow. Home to the country’s longest running dance festival, Jacob’s Pillow astounds dance lovers year after year as it brings in dance companies from around the world. Highlights this year include the season opener, Dance Theatre of Harlem, and the return of Compagnie Kafig, a smash hit last year. Besides the ticketed events, there are free outdoor performances, photography and art exhibits, talks and discussion, dance classes and family-friendly events. International groups will love this venue, they can still get some culture but there is no language barrier to overcome.
  8. MASS MoCA. The largest center for contemporary arts in the United States, housed in renovated 19th-century factory buildings in North Adams, MASS MoCA’s space, exhibits, performing arts celebrate creativity in ways you’ve probably never experienced. Back again this summer is Wilco’s Solid Sound Festival and the FreshGrass Bluegrass Festival. But do look at the schedule; there are fabulous happenings in all genres throughout the summer. Their doors are open year round to groups and there are on-going contemporary exhibits that are sure to please your group.
  9. Chesterwood, a National Trust Historic Site (and country home, studio and gardens of Lincoln Monument sculptor Daniel Chester French) hosts the popular Vintage Motorcar Festival/competition on May 26. The beauty of the property itself is a spectacular backdrop to the display of antique cars. A wonderful place to add to your itinerary where your group can unwind and take unguided strolls or just enjoy the views and then follow it up with an insightful guided tour.
  10. The Berkshire Fringe. Emerging artists present dynamic new works at this homegrown festival held in Great Barrington. This summer, Berkshire Fringe presents 50 artists and ensembles in shows, special events and workshops over the course of 21 days. Got a group that is into the new and edgy, then be sure to make sure they don’t miss out on this fringe festival.
  11. Sterling and Francine Clark Art Institute. Known as “The Clark,” the Williamstown museum presents in-depth and imaginative exhibitions, and this summer’s big show is no exception: Winslow Homer: the Clark Collection, exhibits the greatest collection of works by the American painter assembled by one person. A must see on any Berkshire group itinerary.
  12. Norman Rockwell Museum. The artist himself, though no longer living, may be personally responsible for much of the visitor traffic to the Berkshires, and the Stockbridge museum dedicated to his work and the craft of illustration doesn’t disappoint. Tour Rockwell’s studio and examine the originals of his great iconic works, plus enjoy exhibits such as Snow White and The Seven Dwarfs: The Creation of a Classic, which celebrates the 75th anniversary of the first Disney feature-length animated film. Your group will be charmed by the works of Rockwell along with other great illustrators and they are open year round.
  13. Berkshire Botanical Garden. The always-impressive public display gardens are both functional and ornamental. But exploring the garden isn’t a passive activity, what with all the plants sales, flower shows, garden parties, lectures and workshops and special exhibits bringing visitors back again and again. A great addition to any garden itinerary.
  14. Jewish Film Festival and Summer Celebration of Jewish Music. The 27th season of the Berkshire Jewish Film Festival, sponsored by Congregation Knesset Israel, offers Monday afternoon and evening films at Lenox Memorial High School. The 4th annual Summer Celebration of Jewish Music, co-sponsored by the Jewish Federation of the Berkshires and the area’s Jewish congregations, presents lectures and concerts throughout the Berkshires. Lights, camera and action.
  15. Bascom Lodge. Perched atop Mount Greylock, the renovated rustic stone and wood lodge is the perfect place to enjoy an evening cocktail or a gourmet dinner along with one of the most spectacular views anywhere. Bascom Lodge also invites the public to themed lectures, performances and artist residencies. Not only will your group be charmed by the views but they enjoy a lovely meal.
  16. PS21. An abbreviation for Performance Spaces for the 21st Century, PS21 is a performing arts center under a tent, and its lineup of performances is just as all encompassing, with dance companies, films, youth theater and community singalongs. A little bit of something for everyone.
  17. The Mount. A visit to American author Edith Wharton’s estate and gardens could take a day of its own, but it’s also a cultural destination with a summer lecture series, Music After Hours (jazz on the terrace) and summer theater. Your group is sure to find something to fascinate them here, whether it is the amazing gardens, her remarkable library or ghost tales.
  18. Capitol Steps. The nationally-acclaimed political satire music revue returns to its summer home at Cranwell Resort and Spa in Lenox. Every group needs to have time for a good laugh.
  19. Hancock Shaker Village. Don’t miss this hands-on history tour of a former Shaker village, where artisans demonstrate Shaker crafts, gardeners tend vegetable gardens and guides teach about Shaker worship and work. For a group that wants to get hands on don’t forget to ask about the Build Your Own tours.
  20. Arrowhead. Tour the home of Herman Mellville, where the author wrote Moby-Dick. The 18th -century farmhouse, now a National Historic Landmark, houses the Berkshire Historical Society. The literary buffs in your group are sure to be excited about this venue being on their itinerary.

Click here for our calendar of events. Make sure to see everything there is to do and see in the Berkshires this summer!