Sunday May 19, 2024
Fairytale Farm
Lachat Town Farm
Various times
In final performances, Lachat Town Farm magically becomes an enchanted countryside farm where characters from favorite fairytales live. It’s Hansel and Gretel getting in shape, Pinocchio finding his place as a real boy, no-longer-sleeping Beauty in a new job, Goldie and Baby Bear on Shark Tank, and who knows who else. Games, stories and immersive theater, fun for all ages. Concessions and food carts are on hand, or bring in your own. Tickets, $25, at the link below. Free for children under 5.
Sunday & Monday May 19 & 20, 2024
Spring Book Sale
The Westport Library
Sunday: 11:00-4:00. Monday: 9:00-5:00.
Browse through thousands of gently used books for children and adults in dozens of different categories, plus framed artwork, vintage vinyl records, music CDs, movie and TV series DVDs, jigsaw puzzles, and more. Free admission. Half price on nearly everything on Sunday. Fill a logo bag on Monday for $10, your own bag for $8, or purchase individual items at half price.
Sunday, May 19, 2024
Legally Blonde JR
The Wilton Playshop
15 Lovers Lane, Wilton
3:30 pm & 6:30 pm
Rising Stars Performing arts students present Legally Blonde JR, the fun and upbeat musical that follows the adventures of a sorority girl named Elle Woods — a Gemini with a double Capricorn moon — who tries to win back her ex-boyfriend by earning a Harvard law degree. The performance features talented Weston resident Madelyn Vonk. Tickets, $20–$25, available at the link below.
Westport Dog Festival
10:00 am – 4:00 pm
Winslow Park, Westport
The Westport Weston Chamber of Commerce’s eighth annual Dog Festival is “a three ring circus of activities that will celebrate everything dog, so bring yours.” The festival features demonstrations, competitions, a police K9 presentation, an obstacle course, kids activities, food trucks, and more. Park at the Westport Country Playhouse or designated private lots on the Post Road. Entry is $10 per person and $30 for a family of four (two adults, two children). Proceeds benefit nonprofits. Rain date: June 2. Register a dog for competitions ($5) at the link below.
An Evening with Bernadette Peters
7:00 pm
Westport Country Playhouse
Three-time Tony Award recipient and Golden Globe winner Bernadette Peters takes the stage for an inspiring evening of music from Rodgers and Hammerstein, Stephen Sondheim, Jerry Herman, and others. Known for her work as one of Broadway’s most critically acclaimed performers, Ms. Peters’ career also includes an impressive list of television credits and roles in over 30 films, including a Golden Globe-winning role in “Pennies from Heaven.” Tickets are $175 and $250.
Friday–Monday May 24–27, 2024
Memorial Day Fair
Hurlbutt Elementary School grounds

Friday: 6:00–10:00 pm
Saturday: 2:00–10:00 pm
Sunday: 2:00–10:00 pm
Monday: 12:30–4:00 pm
The traditional Memorial Day Fair with rides, games, hot dogs, cotton candy, and all the typical carnival fare. Sensory-friendly editions of the fair run on Saturday and Sunday from 1:00 to 2:00 both days.
Saturday May 25 & Sunday May 26, 2024
Route 57 West Fest
Memorial Day Fair
Two days at the Fair of musical performances by local bands, talented student musicians and talented parent musicians. Daytime acts include dance troupes and cheer squads. Designed and guided by an Emmy Award-winning executive producer and others, West Fest is a showcase of Weston talent and a hands-on learning experience for the many students involved in staging it.
Saturday May 25, 2024
5K Road Run/Walk
Weston High School
Runners start at 8:30 am
Walkers start at 8:35 am
Kids Fun Run, 8:00 am
Runners, joggers, walkers, and even babies in strollers run or walk in the 5K Road Race on the USATF certified scenic course around the center of town. Trophies and prizes are awarded in several categories. Sign up online (link below) or in person on May 23 and 24 from from 3:00 to 6:00 in the high school cafeteria, or on race day from 7:00 to 8:30 am. Sign up early and you get a t-shirt while supplies last.
Monday May 27, 2024
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, hangs a left, and ends at the Town Hall campus. It’s a good idea to get there early. A memorial ceremony follows at the gazebo. Afterwards, free hot dogs at the firehouse.
Tuesday May 28, 2024
Town Hall Talks
6:00 pm
Town Hall
The debut of regularly scheduled “Town Hall Talks” with First Selectwoman Samantha Nestor. Come with questions and to hear updates on Town activities. The talks will be held on the second Tuesday of each month at 1:00 and on the fourth Tuesday at 6:00. RSVP, required to ensure room availability, by email to executiveassistant@westonct.gov.
Through May 28, 2024
Photography Exhibition: “Water”
Weston Public Library
Community Room
An exhibition of camera artwork by the Weston Library Photography Club on the theme of “Water.” Exhibited photos will be on display in the Community Room on days and during hours the library is open, through May 28.
Thursday May 30, 2024
Afternoon Tea Party
3:00 pm – 5:00 pm
The Women’s Club of Weston warmly invites you to attend their annual afternoon tea party and join in the celebration on the beautifully landscaped grounds of a WCW member. The cost is $25 per person. Checks made payable to WCW, Inc. can be sent in care of Leslie Weiss, 99 11 O’Clock Road, Weston CT 06883. For further information, text 201-575-1475. Rain date is May 31.
Friday May 31, 2024
Raul Midón Performs
8:00 pm
Lachat Town Farm
Singer-songwriter and guitarist Raul Midón performs in Lachat’s Offutt Center, playing his signature blend of smooth folk, alt-pop, and jazz, a “three way fusion of Stevie Wonder, Bobby McFerrin and José Feliciano,” said the New York Times. Mr. Midón has performed with music legends such as Bill Withers, Herbie Hancock, Sting, and with Jimmie Herrod and Renee Fleming to honor Joni Mitchell at the Kennedy Center. Doors open at 6:30 with live jazz by Karl Schulz on the deck and cocktails at the Barn Bar. Purchase tickets, $35, at the link below, with other options.
Saturday June 1, 2024
Paper Shredding and Computer Recycling
10:00 am – 1:00 pm
Hurlbutt Elementary School Bus Loop
Friends of the Weston Library hold a shred day fundraiser in the Hurlbutt Elementary School parking lot. Standard boxes of paper (10"x12"x15") can be shredded for $10 and computers can be recycled for $20 each.
The Arts Bloom in Weston
6:00 pm
Emmanuel Church
285 Lyons Plain Road
Emmanuel Church celebrates local talent with an evening featuring works on display and for sale by professional and amateur artists from Southern Connecticut, live piano jazz by Karl Schulz, a silent auction, and wine and cheese. Tickets, $35, available at the door. Attire is “smart casual.” Please RSVP at the link below. Also there, artists interested in submitting work will find the submission form.
Open Artists Studio
1:00 pm – 5:00 pm
G&B Cultural Center
49 New Street, Wilton
A free Open Studio, a chance to see floor to ceiling art in a variety of media, mingle with the artists, and explore the G&B Cultural Center, a non-profit in Wilton supporting creativity and artistic expression, operating in an historic building in Wilton’s “Georgetown Neighborhood” Historic District. Works include paintings, prints, sculpture, decoupage, glassware, pottery, frames, furniture, and more, all available for purchase.
Saturday June 15, 2024
Music in the Meadow: Clare Maloney & The Great Adventure
6:00 pm – 9:00 pm
Lachat Town Farm
“Windows-down, roadtrip rock and roll” by Clare Maloney & The Great Adventure, whose 2023 debut album “Daybreaker” was hailed by critics for “brilliant vocals, a rocking band, and polished songwriting.” Food trucks are on hand and the Barn Bar will be open. Including the processing fee, tickets (link below) are $33.32. Children under 12 get in for free.
Thursday June 27, 2024
DOT Information Session
7:00 pm
Redding Community Center
The Connecticut Department of Transportation (CTDOT) is conducting a Public Information Meeting concerning the replacement of Bridge No. 01015 on Route 53 just south of the intersection of Glen Road and Newtown Turnpike in the town of Redding.
Ongoing
Weston … What Lies Beneath
Weston History & Culture Center
104 Weston Road
An exhibition of objects found at the Peter Thorp house, one of Weston’s oldest homes, in what started out as a weekend garden project but turned into the uncovering of items spanning two centuries. Open 1:00 pm – 4:00 pm every Thursday and Sunday through March 2, 2025, excluding holidays. Admission $5 for adults, $3 for children, free for WHCC members.

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