Jingle & Jammies

Get ready to kick off the holiday season in the coziest way possible at Jingle & Jammies on Wednesday, December 2, 2026 in Downtown Windsor! Grab your friends, bundle up your little ones in their favorite Christmas pajamas, and enjoy a festive stroll through downtown.
This FREE event is designed especially for moms, caregivers with strollers, and retired adult women—creating a relaxed, cheerful atmosphere to shop, sip, and celebrate the season.
What to Expect:
• Holiday shopping specials from local boutiques
• Delicious brunch bites and festive refreshments
• A magical downtown filled with lights, music, and décor
• Santa wandering the streets spreading holiday cheer
• Plenty of photo-worthy moments in your favorite PJs
?? Bonus: Every registered participant will be entered to win a $200 “Shop Downtown” Gift Card!
Cost: FREE (Registration required to receive your passport to savings)
Date: Wednesday, December 2, 2026
Location: Downtown Windsor
Space is limited—register today and get ready to Jingle & Jammies your way through Downtown Windsor!