Your Guide toWander through downtown Windsor and feel the charm around every corner. Sip your way through local tasting rooms, find a bite to eat, or recharge with a coffee break. From the lively Sunday Farmers Market to afternoons spent exploring one-of-a-kind boutiques, downtown Windsor is vibrant, welcoming, and full of experiences for every local and newcomer.
Come shop small, local businesses and experience a thriving small-but-mighty downtown economy that makes Windsor truly special.
| Light up the Town Green | December 5, 2025, 5-8pm on the Town Green |
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| Santa’s Mailbox | Starting: December 1, 2025 Deadline: December 16, 2025 |
| Charlie Brown Christmas Tree Grove | December 4 through December 31, on the Windsor Town Green |
Directory
Discover hidden gems, locally crafted sips & eats, and family-friendly fun around every corner.
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Explore Windsor, Your Way
There are so many ways to explore Windsor—whether you hop on the SMART Train, taking you right into the heart of downtown’s dining, shopping, and Town Green, or you prefer the convenience of accessible, stress-free parking. However you get here, discovering Windsor is always easy and enjoyable.
