Plan Your Summer Getaway Around Must-See Theatre

14 shows to see at lauded out-of-town venues in Hudson Valley, the Berkshires and beyond

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In terms of COVID-19 safety protocols, masks are optional and proof of vaccination is not required unless otherwise noted.

Barrington Stage Company – Pittsfield, MA

Approximately three hours away from Midtown Manhattan by car, this multi-theatre venue is known for presenting top-notch productions of plays and musicals—this is where The 25th Annual Putnam County Spelling Bee and Mr. Saturday Night first bowed.

A New Brain
Runs August 16-September 10
William Finn’s undersung A New Brain is getting a rare revival coproduced by the Williamstown Theatre Festival. Inspired by Finn’s own brush with death, the musical centers on a songwriter in a slump whose health scare forces him to reevaluate his priorities. What’s more important, art or relationships? James Lapine cowrote the thought-provoking and surprisingly funny book, and Joe Calarco directs.

See Barrington Stage Company’s full summer lineup.

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Bay Street Theater – Sag Harbor, NY

Enhance your Hamptons trip by seeing a show at this modern wharfside playhouse, which is approximately two hours away from Midtown Manhattan by car or the Hampton Jitney.

Tales from the Guttenberg Bible
Runs August 1-27
Actor Steve Guttenberg (Three Men and a Baby, Police Academy, Cocoon) wrote and stars in this new play chronicling his real-life journey from the suburbs of Long Island to the glamor of Hollywood. Expect hilarious, tell-all stories about his career and his encounters with celebrities such as Paul Reiser, Tom Selleck, Kevin Bacon and Merv Griffin.

See Bay Street Theater’s full summer lineup.

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Berkshire Theatre Group – Berkshires, MA

About a three-hour drive from Midtown Manhattan, the Berkshire Theatre Group was founded in 2010 when the Berkshire Theatre Festival and the Colonial Theatre merged. The company presents classic and contemporary works on four stages in two nearby towns: Stockbridge and Pittsfield.

Masks are required for Wednesday matinees.

On Cedar Street at The Unicorn Theatre in Stockbridge
Runs August 12-September 2
Based on Kent Haruf’s novel Our Souls at Night, this world premiere about loneliness, longing and unexpected love comes from Tony-nominated composer Lucy Simon (The Secret Garden), lyricist Susan Birkenhead (Jelly’s Last Jam) and book writer Emily Mann (Having Our Say). Addie (Matilda Tony nominee Lauren Ward) and her neighbor Louis (Love! Valour! Compassion! Tony nominee Stephen Bogardus) lost their spouses years ago, and one day she reaches out hoping to find connection and common ground. What starts out as a platonic relationship blossoms into romance in this moving musical about mourning and moving on. Tony nominee Susan H. Schulman (Sweeney Todd) directs.

See Berkshire Theatre Group’s full summer lineup.

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Dorset Theatre Festival – Dorset, VT

Dorset Theatre Festival is based in a century-old theatre fashioned from a pair of pre-revolutionary barns. Approximately four hours from Midtown Manhattan by car, it’s known as an incubator for new plays, especially works by women.

Still
Runs July 21-August 5
Tim Daly (Wings, Madam Secretary) and Tony nominee Jayne Atkinson star in Lia Romeo’s zany rom-com about two old flames who reconnect 30 years on. But reigniting their passion may blow up their lives, particularly his congressional bid. Adrienne Campbell-Holt directs this two-hander about secrets, second chances and polarized politics.

Ms. Holmes & Ms. Watson Apt, 2B
Runs August 11-26
Kate Hamill is beloved for her radical reinventions of classic lit (Sense & Sensibility, Little Women, Dracula). Her latest comedy puts a feminist spin on Sir Arthur Conan Doyle’s iconic detective and his sidekick, reimagining them as mismatched, modern-day female roommates who banter and bicker as they try to solve a murder mystery.

See Dorset Theatre Festival’s full summer lineup.

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Goodspeed Musicals – Connecticut

Here You Come Again at The Tetris in Chester
Runs July 26-August 27
Hello, Dolly! Parton that is. This jukebox musical cowritten by the hilarious Bruce Vilanch focuses on a devoted Dolly fan getting guidance from an imaginary version of his favorite country crooner. Filled with Parton hits, including “Jolene,” “9 to 5” and the title tune, the show stars cowriter Tricia Paoluccio as the rhinestone-studded, advice-dispensing diva. The third cowriter, Gabriel Barre, choreographs and directs.

See Goodspeed Opera House’s full summer lineup.

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Hudson Valley Shakespeare Festival – Cold Spring, NY

Approximately 75 minutes from Midtown Manhattan by car and also accessible via Metro-North, this company mounts classics and new takes on old favorites in an elegant, open-sided tent overlooking the Hudson River.

Love’s Labor’s Lost
Runs through August 27
One of Shakespeare’s lesser-known romantic comedies gets the musical treatment as four young noblemen swear off women to focus on school, only to find themselves tempted by a quartet of French femmes. Director Amanda Dehnert infuses this rollicking romp with original indie pop songs cowritten by André Pluess.

Penelope
Runs September 2-17
A female-forward reinvention of The Odyssey, this intimate musical is told from the perspective of Penelope as she waits for her husband to return from his 20-year journey while she spurns potential suitors. A musical tribute to all those who wait, hope and dream, Penelope is the brainchild of playwright and songwriter Alex Bechtel.

See Hudson Valley Shakespeare Festival’s full summer lineup.

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Ogunquit Playhouse – Ogunquit, ME

Founded in 1933, the Ogunquit Playhouse specializes in musicals, both world premieres and revivals, given handsome productions in its historic theatre. Located in a seaside resort town, the theatre is approximately five hours from Midtown Manhattan by car.

On Your Feet!
Runs July 20-August 19
The rhythm is gonna get you in this exuberant bio-musical about Grammy-winning singer-songwriter Gloria Estefan, which traces her life and career from her childhood in Miami to international superstardom. Featuring a slew of her hit songs, including “Conga,” “1-2-3,” “Get On Your Feet” and “Coming Out of the Dark,” this show celebrates her music, her Cuban heritage and her tight-knit family.

The Da Vinci Code
Runs August 24-September 23
Dan Brown’s best-selling novel becomes a thrilling stage mystery in this American theatrical premiere. When the curator of The Louvre is murdered, Professor Robert Langdon (Michael Urie) and cryptologist Sophie Neveu (Hannah Cruz) are tasked with solving a series of riddles. Little do they know they’re on the cusp of unearthing a long-buried and deeply personal historical secret. Charles Shaughnessy also stars.

See Ogunquit Playhouse’s full summer lineup.

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Shakespeare & Company – Lenox, MA

This venerable company brings classics by the Bard and others to life through top-notch productions and education programs. In fact, this is where Shakespeare in the Park regular Hamish Linklater got his start thanks to his mom, a founding member.

August Wilson’s Fences
Runs July 22-August 27
August Wilson’s Pulitzer Prize-winning drama centers on Troy Maxson (Brian D. Coats), a blue-collar Black man struggling to provide for his family in the ’50s. Haunted by his complicated past, which includes stints in the Negro Baseball League as well as prison, he takes out his resentment and regret on those he loves most. Part of the playwright’s lauded American Century Cycle.

A Midsummer Night’s Dream
Runs August 1-September 10
The uproarious Jacob Ming-Trent (Merry Wives) is Bottom in Shakespeare’s enchanting romantic comedy about young lovers and magical sprites crossing paths in the woods with hilarious results.

See Shakespeare & Company’s full summer lineup.

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Top image: Corbin Bleu and the cast of Summer Stock at Goodspeed Musicals, which runs through late August. Photo courtesy of the theatre.