Sunday June 14, 2026
Seth Sikes with Rose Levine
6:00 pm
Levitt Pavilion, Westport
Doors open at 5:00
Seth Sikes, one of New York’s standout cabaret performers, brings his signature charm and mischief to songs made famous by broadway female icons like Judy Garland, Bernadette Peters, Liza Minnelli, Barbra Streisand, and Patti LuPone. These diva anthems and torchy tales of love and loss get a fresh spin that’s equal parts reverent and a little bit naughty. A free event. Patrons are welcome to bring outside food and beverages. Get tickets here.
Tuesday June 16, 2026
Isle of Klezbos
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
Lauded by New York Magazine for “cutting edge klezmer,” and the L.A. Blade as “rapturous and rollicking,” the band specializes also in re-grooved standards, obscure vintage soundtrack gems, and genre-defying originals. Isle of Klezbos approaches Yiddish musical traditions with loving irreverence and profound respect. A free event. Patrons are welcome to bring outside food and beverages. Get tickets here.
Wednesday June 17, 2026
Luke Tyler Shelton
7:30 pm
Levitt Pavilion, Westport
Doors open at 6:30
Born in the new millennium, Luke Tyler Shelton makes soul-soothing rock-and-roll with all the ineffable charm of a faraway time, with a profound gift for dreaming up heavenly melodies and fantastically loose grooves. A free event. Patrons are welcome to bring outside food and beverages. Get tickets here.
Thursday June 18, 2026
Dirty Sock Funtime Band
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
The Dirty Sock Funtime Band (DSFB) returns to the Levitt Pavilion’s stage to blast off the Children’s Series with an extra special show, a wild, musical comedy show where anything can happen and everyone is celebrated for who they are! A free event. Patrons are welcome to bring outside food and beverages. Get tickets here.
Friday June 19, 2026
Chris Pierce, Juneteenth Concert
7:30 pm
Levitt Pavilion, Westport
Doors open at 6:30
Chris Pierce is a singular American voice whose songs carry equal parts soul, truth, and grace. Rooted in folk, blues, and Americana, his music speaks plainly and powerfully to the human condition, earning him a reputation as one of the most moving performers of his generation. A free event. Patrons are welcome to bring outside food and beverages. Get tickets here.
Saturday June 20, 2026
Lucius
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
Formed by lead vocalists and songwriters Jess Wolfe and Holly Laessig, acclaimed indie band Lucius is best known for their sinuous harmonies and highly original, pop-noir musical artistry. The group, which includes multi-instrumentalists Peter Lalish and Dan Molad, have released three albums and toured the globe. A ticketed event with various price, seating, food and beverage options. Get tickets here.
Sunday June 21, 2026
Dark Star Orchestra
5:00 pm
Levitt Pavilion, Westport
Doors open at 4:00
Performing to critical acclaim for over 20 years and over 3,000 shows, Dark Star Orchestra continues the Grateful Dead live concert experience. On any given night, the band will perform a show based on a set list from the Grateful Dead’s 30 years of extensive touring or use their catalog to program a unique set list. A ticketed event with various price, seating, food and beverage options. 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.
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.
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.
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.