Entertainment events in Westport

Check out happening entertainment events all around Westport, CT

Harvest Fest 2025

 Sat, 13 Sep at 06:00 pm Wakeman Town Farm USD 189

The Whittingham Cancer Center Concert

 Sat, 01 Nov at 06:30 pm Westport Library

Vic DiBitetto

 Fri, 12 Sep at 07:00 pm Westport Country Playhouse

The Fitzgeralds: A Reading with Music

 Sat, 27 Sep at 07:00 pm Westport Country Playhouse

Vic DiBitetto

 Sat, 13 Sep at 08:00 pm Westport Country Playhouse

TEDESCHI TRUCKS BAND - WESTPORT, CT

 Sun, 14 Sep at 07:00 pm 40 Jesup Rd, Westport, CT, United States, Connecticut 06880

Cooked Up at Black Duck Cafe - Westport, CT

 Sat, 06 Sep at 09:00 pm Black Duck Cafe

New Old Stock returns to the Black Duck Cafe , Westport, CT

 Sat, 13 Sep at 09:00 pm Black Duck Cafe

Vibe Cartel (formerly Southern Fried) returns to VFW Westport

 Sat, 04 Oct at 07:00 pm Westport VFW POST 399

Mark Naftalin $ Friends Blues Party

Sat, 01 Nov at 06:30 pm Westport VFW

STRAWBERRY FIELDS: THE ULTIMATE BEATLES TRIBUTE

 Fri, 12 Sep at 08:00 pm 40 Jesup Rd, Westport, CT, United States, Connecticut 06880

Head of the Charles Rowing Regatta

 Fri, 17 Oct at 05:00 pm Boston Massachussets

Argonaut & Wasp + Wild & Co. – FREE SHOW! NEW DATE: SEPT 20

 Sat, 20 Sep at 07:00 pm 40 Jesup Rd, Westport, CT, United States, Connecticut 06880

Westport Cars & Coffee

 Sun, 07 Sep at 08:00 am Westport Train Station

Amy Irving - FREE CONCERT

 Sun, 07 Sep at 07:00 pm 40 Jesup Rd, Westport, CT, United States, Connecticut 06880

Julian Shively & Emma McDonald: An evening of jazz, R&B and neo-soul ♫

 Fri, 24 Oct at 07:00 am Suzuki Music Schools

Mandy Patinkin in Concert: JUKEBOX

 Fri, 21 Nov at 08:00 pm Westport Country Playhouse

Eliot Lewis Live in Westport, CT

 Sat, 27 Sep at 08:00 pm Westport VFW Auxiliary Post 399

"Psycho" screening hosted by Mark Shanahan

 Fri, 10 Oct at 07:00 pm Westport Country Playhouse

September Comedy Night at Walrus Alley

 Tue, 30 Sep at 06:30 pm Walrus Alley Restaurant USD 29

House on Haunted Hill (1959)

 Sat, 11 Oct at 06:30 pm Earthplace

Jim Savage Live at Westport VFW

Fri, 12 Sep at 05:30 pm Westport VFW

Woodside Bash

 Sat, 04 Oct at 07:00 pm 10 Woodside Ln, Westport, CT, United States, Connecticut 06880

An Evening with Peter Greenberg, The Travel Detective

 Thu, 25 Sep at 07:00 pm The Westport Library USD 23

At This Stage – A gala evening celebrating Westport Country Playhouse’s 95 Seasons!

 Sat, 04 Oct at 07:00 pm Westport Country Playhouse

Continental Connections

 Sat, 18 Oct at 05:00 pm Christ & Holy Trinity Episcopal Church USD 23 to 92

Beardsley Gala

 Sat, 18 Oct at 06:00 pm The Inn at Longshore

🎹 Nawlins Blues Piano Happy Hour – Jim Savage at the Westport VFW

 Fri, 12 Sep at 05:30 pm Westport VFW

October Comedy Night at Walrus Alley

 Mon, 27 Oct at 06:30 pm Walrus Alley Restaurant USD 29

Script In Hand: THE ONE GOOD THING or “Are Ya Patrick Swayze?”

Mon, 08 Sep at 07:00 pm Westport Country Playhouse

Colin Quinn

 Thu, 09 Oct at 08:00 pm Westport Country Playhouse

DNR: The (Almost) All-Physician Rock Band! Annual Tribute to First Responders & Westport EMS: FREE!

Thu, 11 Sep at 07:30 pm 40 Jesup Rd, Westport, CT, United States, Connecticut 06880

Broadway Scores at the Playhouse: Big Band Broadway

 Thu, 29 Jan at 07:00 pm Westport Country Playhouse

The Levitt Pavilion in Westport, CT - In Concert ! on sale ticketing pre-sale available now

 Fri, 12 Sep at 07:30 pm Levitt Pavilion for the Performing Arts, Westport

2025 myTEAM TRIUMPH Westport Triathlon

 Sun, 07 Sep at 07:00 am Westport Compo Beach

Mandy Patinkin

 Thu, 20 Nov at 07:00 pm Westport Country Playhouse

Ana Gasteyer - Sugar & Booze Holiday Spectacular

 Mon, 22 Dec at 07:00 pm Westport Country Playhouse

Fall Festival

 Sun, 05 Oct at 10:00 am 10 Woodside Ln, Westport, CT, United States, Connecticut 06880

Back for some fun and good food-New Old Stock returns to Black Duck Cafe in Westport , CT

 Sat, 08 Nov at 09:00 pm Black Duck Cafe

Recovery Community Development Benefit 2025

 Sun, 19 Oct at 04:00 pm Mitchells of Westport USD 55

Weston Connecticut High School 50th Storytelling Gathering

 Sun, 05 Oct at 09:30 am Sherwood Island State Park

Fall Cooking for the Minis - Grades K-2

 Mon, 08 Sep at 04:15 pm Wakeman Town Farm USD 487

Adventurous Scavenger Hunt! - Westport Village Treasure Trek

 Mon, 16 Dec at 08:00 am 24 Post Rd E USD 15