Tuesday June 9, 2026
At the Levitt: West Point Concert Band
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
The West Point Band in an evening of patriotic music celebrating the United States semiquincentennial, featuring everything from Broadway classics and bluegrass to energetic marches and soaring American melodies. A free event. Patrons are welcome to bring outside food and beverages. Get tickets here.
Thusday June 11, 2026
At the Levitt: Greensky Bluegrass
7:00 pm
Levitt Pavilion, Westport
Doors open at 6:00
Known for their dazzling live performances and relentless touring schedule, Greensky Bluegrass are seasoned road warriors and real people. As with traditional bluegrass, they write about their own contemporary day-to-day happenings, emotions, and experiences in the modern world. A ticketed event with price, seating, food and beverage options. Get tickets here.
Saturday June 13, 2026
Music in the Meadow
6:00 pm – 9:00 pm
Lachat Town Farm
The indie folk-rock band Morningside performs, supported by Charlotte Ross. Performing at popular venues throughout the region and recognized as one of Connecticut’s Top 12 Rising Bands, Morningside’s recent debut album, Answers, explores themes of relationship dynamics, family, grief, and self-discovery. Food trucks will be on site and Lachat’s Barn Bar will be open. Tickets are available here.
Fri. & Sat. June 12 & 13, 2026
At the Levitt: The Disco Biscuits
6:30 pm
Levitt Pavilion, Westport
Doors open at 5:30
The Disco Biscuits, a band of transformation and invention, are a Philadelphia-based group that remains pioneers of “Trance-Fusion,” bridging the gap between electronic dance music and jam rock while looking for new sonic boundaries to break and avenues to tell stories within. A ticketed event with price, seating, food and beverage options. Get tickets here.
Sunday June 14, 2026
At the Levitt: 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
At the Levitt: 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.
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.
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
4th of July Party (on the 3rd)
4:30 pm (gates open)
Weston Middle School Field
Food trucks, ice cream, music, and fireworks at Weston’s annual celebration. 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. Available soon on the Parks & Rec website: a limited number of premier parking spots, $30 each. Also available, ten Tailgate Tent spaces with two parking spots and reserved grass space, $100 each, for decoration, the best view of the field, and a grand prize for the one most creative and spirited.
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
Kickball Tournament
10:00 am – 2:00 pm
A 5th of July event from Weston Parks & Recreation. For three teams of 10 to 12 players: Red (age 15 and up), Blue (families, all ages), and White (mini players age 5 and under). Teams play a minimum of two games, each seven innings or 30 minutes. A team will be built for those without one, upon registration. Food off the Gridiron Grill from 11:00 to 1:00. Registration, $5 per person, available soon on the Parks & Rec website.
Old-Fashioned Field Day
11:00 am – 1:00 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. Sign up on the day at Morehouse.
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.