Sunday May 17, 2026

Art Reception: Peggy Dembicer
2:00 pm – 4:00 pm
Easton Public Library,
691 Morehouse Road, Easton
691 Morehouse Road, Easton
An opening reception for an exhibition of artwork by Weston mixed-media artist Peggy Dembicer, whose recent works explore the integration of acrylics, polymers, beads, metal, and stone, producing distinctive pieces both stimulating and engaging. Much of her art is paper, fiber, and bead weaving that creates pictorial, geometric, and abstract compositions. The Easton Public Library exhibition runs from May 16 through June 30.

Opera Meets Broadway
4:00 pm
Weston Public Library
In the latest edition of Sunday Soundscapes, three outstanding New York City musicians perform fan-favorite arias and duets in Italian and German and operetta and Broadway numbers, including selections from Kurt Weill’s “Street Scene” and Leonard Bernstein’s “Candide.” Admission is free. A donation is suggested, but not required. Reserve seats in advance here.

Queen of the Violin
6:00 pm
SHU Community Theatre
1420 Post Road, Fairfield
1420 Post Road, Fairfield
Kersten Stevens — known as the Queen of the Violin — headlines a one-night-only live recording concert for her upcoming sixth album. Ms. Stevens has performed at renowned venues such as the Apollo Theater and City Winery and has shared the stage with the likes of Ray Charles, Faith Evans, Regina Carter, Kim Burrell, Keyon Harrold and Lakecia Benjamin. The evening will also include special guest appearances by Grammy Award-winning artists. Tickets are available here.
Monday May 18, 2026

Second Wind
7:00 pm
Fairfield Theatre Company
70 Sanford Street, Fairfield
Doors: 6:30
70 Sanford Street, Fairfield
Doors: 6:30
Be among the first to experience Second Wind, an extraordinary new Ukrainian documentary, before it moves to the international festival circuit and awards attention builds. The film follows four amputee soldiers and one wounded female sniper as they take on the challenge of climbing Mount Kilimanjaro, a journey of rehabilitation, resilience, and deep human connection. A Q&A with writer and producer Gennadiy Gazin follows the screening. Tickets, $26 including fees, available here.
Fri. May 22 – Mon. May 25, 2026

Memorial Day Fair
Hurlbutt Elementary School grounds
Friday: 6:00–10:00 pm
Saturday: 1:00–10:00 pm
Sunday: 1:00–10:00 pm
Monday: 12:30–4:30 pm
Friday: 6:00–10:00 pm
Saturday: 1:00–10:00 pm
Sunday: 1:00–10:00 pm
Monday: 12:30–4:30 pm
The traditional Memorial Day Fair with rides, games, hot dogs, cotton candy, and all the typical carnival fair. Sensory-friendly editions of the fair run on Saturday and Sunday from 1:00 to 2:00 both days.
Saturday May 23, 2026

5K Road Run/Walk
Weston High School
5K: 8:30 am
Kids Fun Run: 7:45 am
5K: 8:30 am
Kids Fun Run: 7:45 am
Runners, joggers, and walkers join the 5K Road Race on the USATF certified scenic course around the center of town. Sign up here. The Kids Fun Run on the high school track features a 100-yard dash, a quarter-mile race, and a one-mile race.
Sat. & Sun. May 23 & 24, 2026

Route 57 WestFest
2:00 - 10:00 both days
At the Fair
The popular music festival returns with wall-to-wall performances by 18 acts on a top-notch stage with professional sound engineering.
Monday May 25, 2026

Memorial Day Parade
10:45 am – 12:00 pm
Town center
The annual parade, put on by the Weston Volunteer Fire Department, begins in front of Weston High School, proceeds down School Road to Weston Road (Route 57), then goes up to Norfield Road, turns left, and ends at the Town Hall campus. A memorial ceremony follows on the Town Green. Afterwards, free hot dogs at the firehouse.
Thursday May 28, 2026

WCW High Tea
3:00 pm
Gruel Britannia
161 Cross Hwy., Westport
161 Cross Hwy., Westport
You are invited to the Women’s Club of Weston’s annual high tea, a chance to meet new friends, reconnect with old ones, or bring a guest who might be interested in joining the club after hearing more about its many entertaining activities. These include a book group, potlucks, movie nights, and much more. RSVP by May 23rd if you plan to attend, and send checks payable to WCW, Inc. for $40 per person to WCW, PO Box 1051, Weston, CT 06883.

Jazz on a Summer’s Day
6:30 pm – 9:00 pm
MoCA CT
19 Newtown Tpk., Westport
19 Newtown Tpk., Westport
Experience the intersection of jazz history and visual art at a screening of the 1959 documentary Jazz on a Summer’s Day directed by photographer Bert Stern. The film captures the 1958 Newport Jazz Festival, unfolding as a visual poem that interweaves legendary musical performances with scenes of the coastal crowds and the America’s Cup yacht races. A Q+A with Mr. Kane follows. Tickets, $20 general admission, $10 seniors, $10 students, and free for members,
available here.
Saturday May 30, 2026

Three Towns Bus Tour
10:00 am – 2:00 pm
Commemorating the upcoming 250th anniversary of the Declaration of Independence, a four-hour bus tour exploring the shared history of Fairfield, Weston, and Easton. Three stops on the tour are the c. 1750 Ogden House, Weston History & Culture Center and the Easton Congregational Church and Staples Academy. Light refreshments at some stops. Arrive at the Fairfield Museum (370 Beach Road, Fairfield) at least 30 minutes in advance of the prompt 10:00 departure. Tickets, $80, available here. (Note: the bus does not have wheelchair accessibility.) A program by the Fairfield Museum & History Center, the Weston History & Culture Center, and the Historical Society of Easton.
Sunday May 31, 2026

Music on the Green: Steel Drums
3:00 pm – 5:00 pm
Weston Town Green
Weston goes tropical as the Silver Steel Drum Band performs at the first Music on the Green from the Weston Commission for the Arts. Bring chairs and refreshments to enjoy the high-energy, danceable beats of the band, including Caribbean favorites and the Soca and Calypso music of Trinidad and Tobago. See our story.
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.
