Tuesday September 15, 2026

Comedy Night
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
Doors open at 6:00
John Tobin Presents! delivers a slate of their funniest stand-up comedians for another free night of side-splitting laughs under the stars. This is a free show. Reserve tickets here.
Wednesday September 16, 2026

Westport Community Band
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
Doors open at 6:00
The Westport Community Band, founded in 1977, is composed of adult musicians from Fairfield and Westchester Counties, who represent a wide variety of professional backgrounds and bring diverse musical experiences to the group. This is a free show. Reserve tickets here.
Thursday September 17, 2026

Borboletta
7:30 pm
Levitt Pavilion, Westport
Doors open at 6:30
Doors open at 6:30
A tribute to the music of Carlos Santana, Borboletta keeps true to the afro-cuban, jazz, soul, blues, and rock roots of the music, capturing the electrifying energy of Santana’s live shows. This is a free show. (Rescheduled from August 20.) Reserve tickets here.
Saturday September 19, 2026

Pregame Family Fun Fest
4:30 pm – 6:00 pm
Weston High School
Behind the Booster Barn
Behind the Booster Barn
A fun family event precedes the Weston High School Trojans first home game of the season with a bounce house, face painting, balloon twisting, a bake sale and more. Kickoff for the team’s game is at 6:00.

Music in the Meadow: Stella Blue’s Band
6:00 pm – 9:00 pm
Lachat Town Farm
Stella Blue’s Band recreates the experience of being at a Grateful Dead show by playing the Dead’s music with a deep commitment to authenticity. The band was the first chosen for residency at Garcia’s at The Capitol Theatre, has opened for Carlos Santana, played in the Central Park bandshell and various other NYC venues, and was given a headline spot at the 50th Woodstock Anniversary at Yasgur’s Farm. Purchase tickets here.
Wednesday September 23, 2026

King Stingray
7:30 pm
Levitt Pavilion, Westport
Doors open at 6:30
Doors open at 6:30
Lifelong friends who grew up in a very remote Aboriginal community on the northern tip of Australia, the band blends ancient indigenous melodies with surf, indie and funk influences to create a unique sound. This is a free show. Reserve tickets here.
Friday September 25, 2026

Farmers Market
4:00 pm – 8:00 pm
Lachat Town Farm
An evening of community, live music, fresh food, and family fun with local vendors offering fresh vegetables, flowers, artisanal foods, and unique home goods. For dinner, food trucks and food tents are on site, and you can enjoy a hand-crafted cocktail in the Barn Bar. You can also bring children's books for donation to Little Libraries (see our story). Lower lot parking, $20 and refunded in tokens for most vendor purchases, can be reserved on Lachat’s website, along with information about the children’s area. Park for free on the upper lot at 1 Ladder Hill Road South. Overflow parking is available at the Weston Field Club, with free shuttle service to the farm.
Saturday & Sunday, Sept. 26 & 27, 2026

Connecticut Gold Coast Book Fair
Weston Public Library
Saturday: 10:00 - 5:00
Sunday: 11:00 - 4:00
Saturday: 10:00 - 5:00
Sunday: 11:00 - 4:00
The Friends of the Weston Library host the Connecticut Gold Coast Book Fair, a sale of rare books, antiquarian volumes, signed first editions, collectible children’s books, and ephemera, curated by prominent New England booksellers. Admission is free.
