As we look ahead to the colder months, Kelly and I find ourselves thinking about what winter really means for a town like Middlebury. Yes, it’s brisk. Yes, it’s busy. And yes, it can feel a little quieter once the leaves fall and the days shorten. But winter is also when the heart of a community reveals itself — when small gestures of connection matter more, when a warm welcome in a local shop can brighten a whole afternoon, and when choosing to show up for each other truly keeps the lights on. Winter is when Love Middlebury matters most.
With that spirit in mind, we’ve been exploring new ways to keep our community connected and energized downtown. Our small, owner-run shops and cafés are the backbone of ourtown, and winter is when they need us — and when we, in turn, need them. So we’re dreaming up playful incentives to draw people in, spark conversations, and add a little delight to the season.
One idea we’re excited about is a whimsical “Where’s Waldo?”-style treasure hunt woven throughout downtown. Imagine families, students, and winter wanderers ducking into participating stores, searching for a little character tucked between books, nestled in a window display, or peeking out from a handmade mug. Each visit would invite discovery — not just of the hidden figure, but of the people, products, and stories that make each shop special. Participants could then submit their slips for a chance to win Middlebury Money, turning small adventures into local economic support and giving our town’s businesses a gentle boost at the time of year it’s needed most.
This idea is still evolving, and that’s part of the joy. We want it to be shaped with community input — by the store owners who bring creativity to every display, by families who want activities that get them out and about, by students who love a challenge, and by anyone who believes in the power of a lively, walkable downtown even in the coldest months. So stay tuned as this little spark becomes something bigger. And in the meantime, stay warm, stay curious, and stay connected with us downtown. Winter is long, but Middlebury is strong — and together, we can make the season glow.