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  • Wilton YMCA Halloween Spooktacular and Trunk or Treat

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

    Join the Riverbrook Regional/Wilton YMCA for a Halloween Spooktacular and Trunk or Treat, on Saturday, Oct. 18 from 4-7:30 p.m.! We'll have games, arts and crafts, food trucks, an inflatable bounce house, and of course trunk-or-treating — plus more! And don't forget to wear your costumes! Register on the Wilton YMCA website in advance before prices […]

    $12

  • Great Trains Show

    Wilton Historical Society 224 Danbury Road, Wilton, CT

    One of the most cherished of Wilton’s traditions — a visit to experience the Great Trains Show at the Wilton Historical Society! Take the children in your life to an entrancing afternoon with trains and seasonal excitement. Wilton Historical’s historic 18th and 19th century buildings are charmingly decorated and transformed into a train-lovers delight with […]

    Free – $10

  • Annual Holiday Stroll & Tree Lighting with Santa

    Wilton Center Old Ridgefield Road, Wilton, CT, United States +1 more

    Join the Wilton Chamber of Commerce and local Wilton retailers for a magical Holiday Stroll on Friday, Dec. 5, from 5-8 p.m. Enjoy holiday classics from the Fairfield County Brass Quintet, a marshmallow roast hosted by the Kiwanis Club, and crafts with local businesses. Visit the Wilton Library for sweet treats, a Holiday Book Sale, and […]

  • Historic Cannon Grange Holiday Artisan Market

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

    Stop by the Historic Cannon Grange Holiday Artisan Market on Saturday, Dec. 6, from 10 a.m.-4 p.m. $5 entry supports the Historic Cannon Grange and includes a raffle ticket to enter into any raffle item or drop into the bucket to win a holiday planter! (Additional raffle tickets are available for purchase.) Plus, bid on […]

    $5

  • ‘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 of collecting and trading souvenir pins of your favorite characters and attractions from Disney theme parks to Connecticut! However, there are no restrictions on other […]

    Free

  • Polar Express Day

    Wilton Historical Society 224 Danbury Road, Wilton, CT

    All aboard for an enchanting afternoon! The Wilton Historical Society invites families to join us for Polar Express Day, a special event filled with holiday cheer and unforgettable experiences. On Saturday, Dec. 6 from 2-3 p.m., embrace the winter spirit with the Polar Express and the Great Trains Show. Guests will gather around for a […]

    Free – $5

  • Wilton Community Menorah Lighting

    Join us as the giant outdoor Menorah on the Wilton Town Green shines bright once again, on Sunday, Dec. 14, at 4:30 p.m.! Everyone in the Wilton community is invited to celebrate the Festival of Lights with live music, individually wrapped Chanukah cookies, gelt, dreidels, and fun for the whole family. For the past 19 […]

    Free

  • Winter Solstice Service at Wilton Presbyterian Church

    Wilton Presbyterian Church 48 New Canaan Road, Wilton, CT, United States

    If the Christmastide brings challenges for you, if you are in the midst of loss or grief, if you need a break from the busyness of the season, if you simply want to receive the gift of God among us via music, readings and story, please join Wilton Presbyterian Church for our Winter Solstice service. […]

    Free

  • Christmas Eve Services at Wilton Presbyterian Church

    Christmas Eve Services at Wilton Presbyterian Church
    Wilton Presbyterian Church 48 New Canaan Road, Wilton, CT, United States

    Please join Wilton Presbyterian Church as we celebrate the coming of the Light of the World with two meaningful Christmas Eve worship services on Wednesday, Dec. 24. All are welcome. Family and Candlelight Service at 4 p.m.: A joyful, family-friendly service featuring our church choir, carols and a Christmas message with interactive participation for children […]

    Free