In Winter
  • Iron Horse Music Hall (Northampton, MA): The premiere honky-tonk music venue of central Massachusetts has folk, bluegrass, and rock music nearly every night, from touring artists to local musicians. There’s decent dining, too.
  • Long Wharf Theatre (New Haven, CT): This prestigious company is known for its success in producing new plays that often make the jump to Off-Broadway and even Broadway itself.
  • The Nutcracker (Boston, MA): New England’s premier family-oriented holiday event is Boston Ballet’s extravaganza. When the Christmas tree grows through the floor, even fidgety preadolescents forget that they think they’re too cool to be here.
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  • Portland Stage Company (Portland, ME): One of the outstanding regional theaters in the Northeast, their eclectic August-to-May schedule includes both classic and modern shows, such as The Last Five Years and A Christmas Carol; they have a good track record of developing and producing new American work.
  • Portland Symphony Orchestra (Portland, ME): They’ll knock your socks off from September through May in their series of pops and classical concerts at the Merrill Auditorium.
  • Symphony Hall (Boston, MA): The Boston Symphony Orchestra’s acoustically perfect home also plays host to the Boston Pops and other local and visiting performers worth scheduling a trip around.
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  • Trinity Repertory Company (Providence, RI): In a historic theater building right downtown, this estimable theater company’s resident troupe performs a stimulating mix of new plays and dramatic reinterpretations of classics, from October through mid-June.
  • The Wilbur (Boston, MA): Even in the Athens of America, it’s not all high culture. Comedy’s biggest national names and some regional up-and-comers take the stage at this historic theater, which occasionally books musical acts and storytelling slams.

In Summer

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  • Berkshire Theatre Festival (Stockbridge, MA): An 1887 “casino” and converted barn are homes to stages where both new and classic plays are mounted from June to late October, here in one of the prettiest towns in the Berkshires.
  • The Cape Playhouse (Dennis, MA) is the oldest continuously active professional summer theater in the country, and still one of the best. A parade of stars from Humphrey Bogart to Judy Kuhn has trod the boards in the decades since the 1920s. Performances are staged from mid-June to early September.
  • Hatch Shell (Boston, MA): This amphitheater on the Charles River Esplanade plays host to free music and films almost all summer. On the 4th of July, the Boston Pops provides the entertainment. Bring a blanket to sit on.
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  • Jacob’s Pillow Dance Festival (Becket, MA): This mountaintop farm turned summertime dance center hosts the world’s best and most diverse troupes, often including Pilobolus, the Royal Danish Ballet, and Limón Dance Company. The campus includes a store, pub, tent restaurant, and outdoor stage, where free performances take place most evenings.
  • Marlboro Music Festival (Marlboro, VT): On the campus of Marlboro College, this mid-July-through-mid-August concert series brings together some of the biggest names in classical music with gifted students—the stars of tomorrow.
  • Newport Folk Festival and Newport Jazz Festival (Newport, RI): The only thing better than hearing live folk or jazz music in Fort Adams State Park on a summer weekend is anchoring your boat near enough to listen free. These two enduring festivals bring top acts to the City by the Sea.
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  • Ogunquit Playhouse (Ogunquit, ME): This is summer stock. The 750-seat theater has been showcasing lively plays since 1933; famous actors like Bette Davis, Tallulah Bankhead, and Sally Struthers (though not all at the same time!) have taken the spotlight each summer in beloved and brand new musicals. Performances usually run from mid-May through late October.
  • Shakespeare & Company (Lenox, MA): Sprawled across a bucolic 33-acre property, this theater company presents diverse works indoors and outdoors in the new Roman Garden Theatre. A night here is one of the many civilized ways to enjoy an evening in the Berkshires during the summer and beyond.
  • Tanglewood (Lenox, MA): By far the most dominating presence on New England’s summer cultural front, this magnificent Berkshires estate is the summer playground for the Boston Symphony Orchestra, plus it also makes room for popular artists such as James Taylor and Harry Connick, Jr.
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  • Williamstown Theatre Festival (Williamstown, MA): Classic, new, and avant-garde plays are all presented during the late-June-through-August season at this venerable festival. There are two stages including an intimate venue for less mainstream or experimental plays, typically making their world premiere. 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.