
Holiday Stroll 2026

Gather your neighbors, friends, and family and join us for the Wilton Holiday Stroll on Friday, December 4th, from 4:30 to 7:30 PM for an evening of holiday cheer!
The night will be alive with music and joy as a local children’s choir kicks off the live entertainment on the Town Green at 4:45pm. Follow the sounds of seasonal classics performed by the Fairfield County Brass Quintet, and wrapping up the live performances will be the Saint Matthew’s Episcopal Church choir as they fill the air with song, performing live at the Town Green and caroling through the streets of Wilton Center with harmony. Additional fun and activities will include: 
• Roaring Bonfire & Marshmallow Roast: Head over to the Legion Post building across from the Town Green where the Kiwanis Club is hosting a cozy bonfire to keep you warm and toasty.
• Holiday Crafts & Shopping: Explore the Town Green, where local nonprofits are hosting fun kids’ activities and offering unique items to help you cross off your shopping list.
• Library Treats & Treasures: Wilton Library staff will be outside their front entrance from 4:30 to 7:00 p.m. handing out special gift bags with sweet treats, while supplies last. Children can also visit the Children’s Library to make a special bookmark, and all visitors are encouraged to browse for gifts and stocking stuffers at the Holiday Book Sale in the gallery, and to view the new art show.
• Hanukkah Sweetness: Celebrate Hanukkah with the community and enjoy delicious festive treats generously provided by Chabad of Wilton.
• Food Trucks: Delight your tastebuds as local food trucks and select dining options will be available to keep everyone fueled for the fun.
• Festive Music: Dance away at the Town Green to holiday classics as a local DJ keeps the holiday tunes hopping and the festive energy high throughout the event!
• Capture the Magic: Look out for local photographer Courtney Krankall, who will be capturing the evening’s smiles and unforgettable moments.
🎅 Tree Lighting and Santa’s Grand Arrival
Gather together for the annual tree lighting at 5:00 pm then keep your eyes peeled for the Wilton Fire Department as local firefighters escort Santa Claus into town on the spectacular Ladder 5 fire truck! Children can share their holiday wishes with Santa at the Gazebo from 5:30-7:30pm.
🛍️ Share the Joy & Shop Local
Support the heart of our community by shopping local. Take a festive stroll through Wilton Center, where participating retailers will welcome you with open doors, delightful light bites, and holiday refreshments.
This beloved community tradition is proudly sponsored by Kimco Realty, in partnership with the Town of Wilton, the Wilton Fire Department, Wilton Kiwanis Club, and a very special collaboration with the Wilton Playshop. Come out, share in the joy, and help us kick off a spectacular holiday season in the heart of Wilton! The Holiday Stroll is a rain or shine event.
For more information, contact Camille Carriero, Executive Director at info@wiltonchamber.com or 203-762-0567.