• The Great Trains Holiday Show at the Wilton Historical Society

    Wilton Historical Society 224 Danbury Road, Wilton, CT

    Model trains, holiday cheer, and family fun returns with one of Wilton’s favorite holiday traditions, the Great Trains Holiday Show! Explore the Wilton Historical Society’s 18th- and 19th-century historic buildings — charmingly decorated for the holiday season — to find multiple layouts of model trains that wind their way through miniature winter landscapes, vibrant towns, […]

    $5 – $10
  • Trackside Movie Night: HOME ALONE!

    Trackside Teen Center 15 Station Road, Wilton, CT, United States

    Holiday Trivia challenge with prizes and Little Nero's Pizza slices free with $15 admission

    $15.00
  • Jingle All the Way with Music on the Hill

    Wilton Historical Society 224 Danbury Road, Wilton, CT

    Join Music on the Hill at the Wilton Historical Society as they perform festive holiday carols and winter songs with singers and ringers! Jingle All the Way will take place on Saturday, December 3 from 2:00 – 3:00 outside by the Abbott Barn. Perfect for all ages, and includes a fun jingle-bell craft. No charge, […]

    Free
  • Breakfast with Santa At The Cannon Grange

    The Cannon Grange 25 Cannon Rd., Wilton, CT, United States

    Enjoy a pancake breakfast with Santa Bill at the Cannon Grange on Sunday, Nov. 26. The cost per person is $12, which includes a delicious pancake breakfast with Santa, a photo op with Santa, face painting and music to enjoy. Three sessions: 9-9:45 a.m.; 10:15-11 a.m.; and 11:30 a.m.-12:15 p.m. Register online or use the […]

    $12
  • Wilton Library: Holiday Stroll

    Wilton Library 137 Old Ridgefield Rd., Wilton, CT

    Wilton Library staff will welcome visitors during this year’s Holiday Stroll on Friday, December 1. Outside our front entrance, we will be handing out special gift bags with sweet treats, while supplies last. Children can stop by the Children's Library to make a special bookmark to take home with their books! We invite all visitors […]

    Free
  • Celebrate Lunar New Year!

    Wilton YMCA 404 Danbury Rd., Wilton, CT, United States

    The Wilton Y invites the community to join in celebrating Lunar New Year — the Year of the Dragon. Find holiday snacks and prizes in the lobby of the Y along with storytimes at 11 a.m. and 12:30 p.m. Little ones will enjoy preschool-age stories at both times.

    Free
  • Community Thanksgiving @ Trackside

    Trackside Teen Center 15 Station Road, Wilton, CT, United States

    Join Trackside Teen Center in celebrating gratitude and connection with a wonderful community at their inaugural Family & Friends Thanksgiving. They invite participants to bring a dish that holds special meaning for their family during the holidays to share with everyone. ​Trackside looks forward to slowing down, learning about everyone's families' cultures and enjoying a […]

    Free
  • Marché Holiday Market

    WEPCO Complex

    Marché brings unique local flair to Wilton’s Holiday Market. Shop local, support community, and celebrate the season. Marché, a highly anticipated local artisan market, transforms WEPCO Parish Hall (St. Matthew’s Wilton) into a bustling bazaar of artisanal goods and holiday cheer on Saturday, November 30. It focuses on celebrating local artisans and small businesses for […]

    Free
  • Buddy’s Winter Wonderland @ Trackside

    Trackside Teen Center 15 Station Road, Wilton, CT, United States

    Join Buddy the Elf for a night of festive fun and a Taylor Swift birthday celebration at Trackside Teen Center! Enjoy ELF, the movie; cookie decorating; cake for Tay Tay; holiday prizes; Taylor trivia and most festive FIT; games and more... Open to grades 6+.

    Free
  • ‘TheDisneyPinventory’ Pin Trading Event

    Comstock Community Center

    An afternoon of pin trading fun! Pin trading is a popular hobby where people come together to exchange collectible pins.  This event focuses on Disney pins — bringing the tradition […]

    Free