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15 Shows to Road Trip to See This Summer

May 29, 2019 by Ali Bloomston
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We’re not sure we agree with Aaron Burr when he says “there’s nothing like summer in the city.” We tend to be more in Eliza’s camp of needing to “run away with us for the summer, and go upstate.”

Living in the city means you have theater and culture at your fingertips, but sometimes there are events worth the schlep beyond the MTA’s reach. Don’t miss these shows in our Summer Destinations, all just a short journey from the city.

Check out our Summer Destinations offerings in the Hudson Valley, the Hamptons, Vermont, Maine, and more.

Into the Woods at Barrington Stage Company
Barrington Stage Company’s upcoming production of “Into the Woods” is the talk of the town, and we’re not just talking about Great Barrington. The show features big Broadway names, like Mykal Kilgore (“Motown the Musical”) as the Witch, Mara Davi (“Dames at Sea”) as the Baker’s Wife, and Jonathan Raviv (“The Band’s Visit”) as The Baker. In celebration of Barrington Stage Company’s 25th anniversary season, we’ve partnered to bring you $25 mobile Rush tickets all season-long.

Acquanetta at Bard Summerscape
The current Broadway production of “Oklahoma!” directed by Daniel Fisher originated at Bard Summerscape in 2015, and now the Ton nominee is the mastermind behind the Bard production of “Acquanetta.” The horror-comedy combines theater, opera, and film and is a summer must-see.

Rock and Roll Man at Berkshire Theatre Group
Everyone loves to be the first to discover a hot show so make sure to catch the Broadway-bound “Rock and Roll Man” at Berkshire Theatre Group. The show explores influential and controversial rock-and-roll legends, and features original songs alongside well-known hits from the ’60s, including “Why Do Fools Fall in Love” and “Great Balls of Fire.”

Across the Stars: Music of John Williams at Tanglewood
Pack your picnic blanket and enjoy the music of John Williams under the stars. The program features violinist Anne-Sophie Mutter and includes selections from Williams’s most iconic scores including “Star Wars” and “Harry Potter.”

Into the Woods at Hudson Valley Shakespeare Festival
To answer Cinderella: “I still wish to go to the festival. But how am I ever to get to the Festival?” We’d just like to let her know we have $15 Rush tickets to all Hudson Valley Shakespeare Festival shows. No mother in a tree needed. Trust us when we say there’s nothing more magical than seeing “Into the Woods” performed in the literal woods.

Curtains at Mac-Haydn Theatre
The charming theatre in Chatham, NY is kicking off their summer 2019 season with Kander and Ebb’s whodunnit musical “Curtains.” Hilarity ensues when a leading lady dies

Laura Benanti at Caramoor
Our hearts are still breaking that “My Fair Lady,” starring Laura Benanti, is closing on Broadway, but you can catch the Tony Award winner in Hudson Valley and have her serenade your worries away in her show “Tales from Soprano Isle.”

Cabaret at Peregrine Theatre Ensemble
Come taste the wine and hear the band at Peregrine Theatre Ensemble’s production of the bawdy and dark classic “Cabaret.” According to Provincetown Magazine, “Peregrine Theatre Ensemble ​manages to do it as well as anyone, on or off-Broadway ever could.” So we’d say that’s worth the short journey to P-town.

Catch Me If You Can at New London Barn Playhouse
Head up to New Hampshire for this musical based on the Tom Hanks and Leonardo DiCaprio movie featuring a score from Marc Shaiman and Scott Wittman. If that’s not enough of a selling point, we have $18 Rush tickets to all New London Barn shows this summer.

Dig at Dorset Theatre Festival
Theresa Rebeck, the playwright behind “Bernhardt/Hamlet” and writer behind “Smash,” presents and directs the world premiere of her newest work “Dig” in Dorset, Vermont. The show is described as a play about “courage, redemption, and photosynthesis” and honestly, we’re intrigued.

Peter and the Starcatcher at GhostLit Repertory Theatre Company
New to the Berkshires theatre scene, GhostLit Rep strives to create innovative and transformative works. Plan your trip to the Berkshires for the last weekend in June, when the GhostLit team resents the Tony Award-winning “Peter and the Starcatcher” at the historic Saint James Place.

Beauty and the Beast at Sharon Playhouse
It’s the tale as old as time, and it’s being told in the cutest barn-turned-theater you’ve ever seen. Sharon’s Playhouse is only two hours outside the city in Connecticut, and this Disney classic is well worth the day trip.

Jeremy O. Harris and Emily Bobrow in Conversation at Twenty Summers
Vogue named Jeremy O. Harris “one of the most promising playwrights of his generation” and Out magazine titled a piece “Meet Jeremy O. Harris: The Queer Black Savior the Theater World Needs.” Sounds pretty impressive, no? The playwright behind “Slave Play” and “Daddy” speaks with journalist Emily Bobrow, for a conversation that is sure to be the talk of Provincetown.

I Love You, Your Perfect, Now Change at Theater Barn
If you think going on Hinge dates is a nightmare, this show at the Theater Barn in the Berkshires is for you. The musical celebrates contemporary romance in a hilarious revue, with new songs and revised lyrics and dialogue that reflects the complexities of dating today.

The Merry Wives of Windsor at Shakespeare & Company
Who doesn’t love a little Shakespeare in the Park? Shakespeare and Company presents this antics-filled comedy in their stunning Roman Garden Theatre. World-class theatre and a sunset? Yes please.