Saturday December 13, 2025
Stuff a Police Cruiser
10:00 am – 2:00 pm
Weston Shopping Center
Help fill a patrol car with gifts to brighten the holidays for local families and children in need. All donations support Toys for Tots, Weston Social Services, and local houses of worship. The police are also accepting donations of new hats, gloves, socks, and underwear for adults and children. Donations can also be dropped off through December 15 in collection boxes inside the Police Department lobby.
Mark Twain Juried Art Show
10:00 am – 5:00 pm
The Mark Twain Library,
439 Redding Road, Redding
Sunday: 1:00 pm – 5:00 pm
The 53rd Annual Mark Twain Library Juried Art Show continues, running through December 14 with works by more than 175 local and world-renowned artists on display and for purchase in a charming and festive gallery setting. 35 percent of proceeds go directly to the library. The artworks are also available to view and buy in an online gallery.
Sunday December 14, 2025
Lachat Winter Market
10:00 am – 2:00 pm
Lachat Town Farm
A select group of local vendors and farms sell art, clothing, jewelry, housewares, baked goods, and locally produced foods. In the farmhouse, enjoy eats from food vendors offering baked breads, pastries, frozen dumplings, Mexican food, and more. Singers from New Paradigm Theatre appear at 11:15. Festive craft cocktails, wine, and hot cocoa are available at the Barn Bar. Also, share warmth by bringing gently worn coats that will be donated to Open Doors of Norwalk.
Tuesday December 16, 2025
Community Menorah Lighting
6:00 pm
Weston Shopping Center
All are welcome at the traditional lighting of the giant menorah led by Rabbi Levi Stone of the Schneerson Center for Jewish Life, CT, marking the Festival of Lights. The event features live music, individually wrapped Chanukah cookies, gelt, dreidels, and family-friendly holiday fun.
Fri. & Sat. December 19 & 20, 2025
Coley House Christmas Tours
Weston History & Culture Center,
104 Weston Road
Friday: 6:00 and 7:30.
Saturday: 4:30, 6:00, and 7:30.
Explore the historic Coley House decorated as it would have been for Christmas in the 1940s. Enjoy live music from the jazz duo “On The Count of Two” and holiday treats made from World War II ration recipes. See authentic 1930s and 1940s holiday decorations, learn how World War II affected holiday celebrations, and listen to original radio broadcasts. Purchase tickets in advance here, $15 for WHCC members, $25 for non-members.
Sat. & Sun. December 20 & 21, 2025
Candy Cane Hunt
Lachat Town Farm
5:30 pm and 7:00 pm
Recommended for children ages 4 to 12, a search for candy canes hidden in the woods and meadow of Lachat Town Farm. Bring a flashlight and dress for winter weather. Also enjoy a s’mores roast at the fire pit, festive music, and a photo op in the barn. Rain or shine. Tickets are available here. $15 for children who bring a new toy to donate to the Domestic Violence Crisis Center, $20 for those arriving without a toy. Lachat uses the extra $5 to purchase gift cards for the DVCC. Free for adults, who must accompany children.
Monday December 22, 2025
Sugar & Booze Holiday Spectacular
7:00 pm
Westport Country Playhouse
The Playhouse presents Saturday Night Live alumna Ana Gasteyer, performing selections from “Sugar & Booze,” her album of seasonal favorites and holiday originals that topped numerous lists of the best holiday albums. Tickets are $95, $115, and $125. Full details are available here.
Saturday January 10, 2026
Save a Life: Hands-Only CPR
10:00 am – 11:30 am
Location TBD
A free class by Weston EMS on recognizing medical emergencies, hands-only CPR, and how to use a defibrillator. Participants practice on Smart Manikins. 70 percent of out-of-hospital cardiac arrests happen at home. Only 10 percent survive, but immediate CPR doubles or triples that rate. Sign up here.