Comedian Joe Pontillo, who recently performed at Laughing Gas Comedy Night, shared his thoughts on Westporters and will return to the VFW on October 17 with fellow New York comedian Ellen Karis.

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.

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.

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.

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.

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.

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.

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.