Tuesday June 23, 2026
Time Capsule Ceremony
9:30 am
Weston Intermediate School Auditorium
In 1976, a group of Weston fifth graders buried a time capsule on the grounds of Weston Middle School. 50 years later, alumni, students, educators, and community members are invited to gather and celebrate the connection between Weston’s past and future as the time capsule torch is passed to today’s fifth graders. Email Aline Weiller — alineweiller@me.com — to be added to the required sign-in list.
Tuesday June 23, 2026
Rolling Together Revue
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
Three standout acts come together. G. Love is an American singer, rapper and musician, the frontman for the band G. Love & Special Sauce. Donavon Frankenreiter entertains with a blend of laid-back grooves, philosophical lyrics and soulful delivery. Moon Taxi is a Nashville-based indie alt-rock band. A ticketed event with various price, seating, food and beverage options. Get tickets here.
Wednesday June 24, 2026
Son Little with Tonina
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
Son Little’s live show is raw, expressive, and always evolving, moving between deep grooves, stripped-down intimacy, and moments that feel completely improvised. Tonina is a vocalist and bassist, playing a rich blend of jazz, folk, and Latin boleros. A free event. Patrons are welcome to bring outside food and beverages. Get tickets here.
Thursday June 25, 2026
Miss Tutti & the Fruity Band
7:00 pm
Levitt Pavilion, Westport
Lawn opens at 6:00
Children’s Series: Miss Tutti and The Fruity Band is a musical project celebrating themes of confidence, inclusivity, and LGBTQ+ representation for kids and families, playing upbeat retro-pop tunes. Think Mr. Rogers meets The Monkees. A free ticket show. Patrons are welcome to bring outside food and beverages. Get tickets here.
Friday June 26, 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. Lower lot parking, $20 and refunded in tokens for most vendor purchases, is available here on June 12. Free upper lot parking at 1 Ladder Hill Road South. Overflow parking at Weston Field Club, with free shuttle service to the farm.
Chaparelle
7:30 pm
Levitt Pavilion, Westport
Doors open at 6:30
Singer-songwriters Zella Day and Jesse Woods come together to reveal their highly anticipated collaboration, “Chaparelle,” a partnership that channels country music’s golden age, weaving a melodic narrative. A free ticket show. Patrons are welcome to bring outside food and beverages. Get tickets here.
Saturday June 27, 2026
Politics & Pie
12:00 pm – 1:00 pm
Weston Public Library lawn
State Senator Ceci Maher and Representative Anne Hughes discuss state and local affairs and answer questions at this Weston League of Women Voters event, held outdoors on the lawn if weather permits, indoors if it doesn’t.
Circles Around the Sun
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
This Los Angeles-based supergroup is a contemporary instrumental rock band, initially formed in 2015, when Justin Kreutzmann, son of Grateful Dead drummer Bill, invited founder Neal Casal to compose the intermission music for the Dead’s “Fare Thee Well” concerts. A free ticket show. Patrons are welcome to bring outside food and beverages. Get tickets here.
Sunday June 28, 2026
Music at the Barn
5:30 pm – 7:00 pm
Weston History & Culture Center
104 Weston Road
One Bad Oyster, “a band assembled to celebrate the good life,” plays upbeat ska and surf tunes on the grounds of the Coley Homestead. Bring a picnic dinner, a bottle of wine, and enjoy the music. Tickets are $15 each for WHCC members, $20 for non-members. Free for children 12 and under. Purchase tickets in advance here or at the door.
Jazz at Lincoln Center Orchestra With Wynton Marsalis
Levitt Pavilion, Westport
Doors open at 5:45
This performance is part of the lead-up to Wynton Marsalis’s final season as Artistic Director of Jazz at Lincoln Center and Music Director of the Jazz at Lincoln Center Orchestra. At 6:00, an opening set by Jazz at Lincoln Center Youth Orchestra. At 7:00, the performance by Jazz at Lincoln Center Orchestra with Wynton Marsalis will begin and feature two sets. A ticketed event with various price, seating, food and beverage options. Get tickets here.
June 30, 2026
Comedy Night #1: Pride Edition
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
John Tobin Presents! delivers a slate of their funniest stand-up comedians for a free night of laughs under the stars. A free ticket event. Patrons are welcome to bring outside food and beverages. Get tickets here.
Friday July 3, 2026
3rd of July Fireworks
4:30 pm (gates open)
Weston Middle School Field
Not on the 4th this year, the annual town party with food trucks, ice cream, music, and fireworks at dusk, around 8:30. At 5:30, the Westport Community Band perform. At 6:30, it’s Owen Daniel. At 7:30, Fake ID. Tickets $20 per car, $5 for walk-ins. See the Parks & Rec website for information about a limited number of premier parking spots, $30 each, and ten Tailgate Tent spaces with two parking spots and reserved grass space, $100 each.
Saturday July 4, 2026
National Bell Ringing
2:00 pm
All around town
A nationwide tolling of bells 13 times, where people will ring cow bells, dinner bells, bicycle bells and all manner of bell signifying the original 13 colonies and celebrating Independence Day.
Sunday July 5, 2026
Old-Fashioned Field Day
10:00 am – 2:00 pm
Morehouse Field
A 5th of July event from Weston Parks & Recreation featuring a tug-of-war, leaky cup relay, sack racing, egg and spoon relay races, a t-shirt relay, a three-legged race, a Lady Liberty torch race, and leapfrog. Also, a kickball tournament for three teams, each 10 to 12 players, organized mainly in age groups. See the Parks & Rec website for details.
Sunday July 26, 2026
Music at the Barn
5:30 pm – 7:00 pm
Weston History & Culture Center
104 Weston Road
Faded is the Crimson, led by guitarist JD Seem of the “Faster Things” Allman Brothers tribute band, celebrates the Grateful Dead live acoustic album “Reckoning” and revives the spirit of those intimate 1980 shows. Tickets are $15 each for WHCC members, $20 for non-members. Free for children 12 and under. Purchase tickets in advance here or at the door.