Westport Community Theatre launches its 68th season with “Dooley at the Bar,” an original one-man play created and performed by Alexander Kulcsar. Directed by Michael Stanley, the show celebrates the wit and wisdom of Finley Peter Dunne’s iconic character, Mr. Dooley. Runs Sept. 12–28.
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The Westport Journal’s Fall Culture Preview highlighted the abundance of theater, art, books, and film events across Connecticut this season
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Westport Community Theatre will hold auditions Tuesday, Sept. 2, for its November production of Conscience by Joe DiPietro. Directed by Alexander Kulcsar, the play tells the story of Senator Margaret Chase Smith, the only Republican senator to stand against Joseph McCarthy in the 1950s.
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Get ready to laugh out loud as Comedy Night returns to VFW Post 399 in Westport on Friday, Sept. 5. Steve Marshall headlines an evening of sharp wit and big laughs, joined by comedians Joe Pontillo, Cara Amore, and Brad Bruckner. Presented by Laughing Gas Comedy, the show runs 8–10:30 p.m., with doors opening at 7.
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Westport Country Playhouse launches its 2025-26 season with “Tuesdays with Morrie,” Sept. 4–6. Starring Broadway legend Len Cariou and Christopher J. Domig, the award-winning play brings Mitch Albom’s beloved memoir to life with humor, wisdom, and moving lessons on love and mortality.
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Westport native Joe Gelini, a Staples ’95 grad, now leads Cha Wa, a twice-Grammy-nominated New Orleans band that blends brass, funk, and Mardi Gras Indian tradition. Their fourth album, Rise Up, releases Aug. 29—20 years after Hurricane Katrina.
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The Grammy Award-winning Tedeschi Trucks Band will perform Sunday, Sept. 14, at the Levitt Pavilion. VIP tickets for Levitt members go on sale today, Aug. 22, at 10 a.m., with general sales beginning Sunday, Aug. 24.
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Rock & Roll Hall of Famer John Oates brings his Good Road Band to town on Friday, Aug. 22 at 7 p.m. for a night of timeless hits and fresh grooves. Dance to the classics you love from the Hall & Oates era, plus brand-new songs from his upcoming solo album, “OATES.” Full bars, food trucks, and an unforgettable night of music under the stars. Doors open at 6:30 p.m.
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First Folk Sunday on Sept. 7 will feature Kevin Burke, hailed as one of the greatest Irish fiddlers of the past half-century, and rocker John Brennan in a unique performance blending Irish, rock, and bluegrass styles at the Saugatuck Rowing Club.
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What’s hot in Westport culture this fall? Experts in theater, film, literature, and art will preview must-see local events on Sept. 4 at the Westport Library.
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New Yacht City, a seven-piece yacht rock cover band, brings classic hits and big energy to VFW Post 399 in Westport on Saturday, Aug. 9.
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WESTPORT—Broadway performer Linedy Genao will take the stage at Westport Country Playhouse on Aug. 12 in Songs from My Sala, a concert that traces her journey from living room performances to starring roles on Broadway.
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WESTPORT–The Flying Fingers Jug Band is back for their third headline appearance at First Folk Sunday on Aug. 3, bringing their lively, prohibition-era Southern jug band sound to the Saugatuck Rowing Club.
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Dark Star Orchestra brought its signature Grateful Dead-inspired sound to the Levitt Pavilion in Westport, performing a ticketed show that supports free summer events.
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Grammy Award-winner José Feliciano will headline “Summer Jam,” a concert fundraiser at Westport Country Playhouse on Aug. 15, benefiting the Church of the Assumption’s 150th anniversary campaign.
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Westport Country Playhouse will host its 2nd Annual Golf Tournament fundraiser on Monday, July 21 at Birchwood Country Club. The full-day event includes 9- or 18-hole scramble play, contests, lunch, cocktails, and prizes — with proceeds supporting the Playhouse’s artistic and educational programs.
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The Miró Quartet will play MOCA/CT on Saturday night. The Grammy-nominated and Emmy-winning group will perform pieces by Hayden, Ginastera and Ravel.
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Candace Bushnell performs her hit off-broadway show “True Tales of Sex, Success, and Sex and the City” at the Westport Country Playhouse.
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Concert series begins its third season with a tribute to singer Linda Rondstadt. Sisters Suzanne Sheridan and Christine Erskine will perform.
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Westport songwriter best known for 90s radio hits as well as TV and movie soundtracks, debuted her playwriting skills with special performance Monday evening.
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As the War for American Independence rages on, General George Washington must depend on his trusted spy network for key intelligence about British movements. In our brand-new Escape Room experience […]
As the War for American Independence rages on, General George Washington must depend on his trusted spy network for key intelligence about British movements. In our brand-new Escape Room experience […]
As the War for American Independence rages on, General George Washington must depend on his trusted spy network for key intelligence about British movements. In our brand-new Escape Room experience […]
As the War for American Independence rages on, General George Washington must depend on his trusted spy network for key intelligence about British movements. In our brand-new Escape Room experience […]
As the War for American Independence rages on, General George Washington must depend on his trusted spy network for key intelligence about British movements. In our brand-new Escape Room experience […]
As the War for American Independence rages on, General George Washington must depend on his trusted spy network for key intelligence about British movements. In our brand-new Escape Room experience […]
As the War for American Independence rages on, General George Washington must depend on his trusted spy network for key intelligence about British movements. In our brand-new Escape Room experience […]
Comedy comes to MoCACT as Circle Comedy and Westport Parks & Rec bring you a night of stand-up headlined by Christian Finnegan the sharp-witted comic known for Chappelle's Show, VH1's […]
As the War for American Independence rages on, General George Washington must depend on his trusted spy network for key intelligence about British movements. In our brand-new Escape Room experience […]
Comedy comes to MoCACT as Circle Comedy and Westport Parks & Rec bring you a night of stand-up headlined by Christian Finnegan the sharp-witted comic known for Chappelle's Show, VH1's […]
Westport Country Playhouse stages the world premiere of “Ken Ludwig’s Pride and Prejudice, Part 2: Napoleon at Pemberley,” written by Ken Ludwig and directed by Emily Mann, October 20 - […]
November 6 - 22, 2026 ALWAYS…PATSY CLINE Written by Ted Swindley Always…Patsy Cline is more than a musical tribute to the legendary country singer who died tragically at age 30 […]
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