OffBeat Pathfinder Basecamp

There’s a reason Woodstock ends up on every “cutest small town” list, and it’s not just the maple syrup. I spent a long weekend here last October, and it’s as picture-perfect as the postcards claim—think covered bridges, steepled churches, and a downtown so charming you’ll forget you came for the hiking.

My B&B was run by a couple who looked straight out of a Hallmark movie, and every breakfast featured blueberry pancakes with local syrup. Downtown, you’ll find shops with handmade crafts, stacks of flannel shirts, and enough farm-to-table cafés to make your Instagram blush. If you time it right, you’ll catch the foliage at its fiery peak—locals swear by the Ottauquechee River walk for leaf-peeping.

Billings Farm is a must (free cheese samples, need I say more?), and if you’re brave, drive up to Mount Tom’s summit at sunrise—bring a camera and a sweater, you’ll need both. I caught a local bluegrass show at the Town Hall and left with a Vermont cheddar addiction.

Question: Who else has wandered Woodstock? Favorite finds, food stops, or hidden trails?

P.S. The general store fudge is dangerous. You’ve been warned.

I grew up an hour from Woodstock, and it still blows me away every visit. The Woodstock Farmers’ Market has the best apple cider donuts—get there early before they sell out. For a different vibe, try the Marsh-Billings-Rockefeller National Historical Park trails. And yes, Billings Farm’s cheese curds are basically currency in my house.

Love this thread! I stayed in a retro camper just outside town last spring—walked to Sugarbush Farm for maple samples and nearly rolled back down the hill. If you like quirky museums, the Vermont Toy Museum is worth an hour, especially if you’re a kid at heart.

Woodstock in the snow is pure magic—hit the local bakery for fresh cinnamon rolls and hot cocoa after a morning exploring. If you’ve got kids (or just act like one), check out VINS Nature Center for their raptor shows. Anyone else get lost in the labyrinth at Prosper Valley?