In the Northeast, there are roughly 10 minutes between the collective acceptance that summer is over and the first (cursed) day of puffer season. OK, that might be a slight exaggeration — there’s at least enough time for a trip to Woodstock, Vermont.
You’d be forgiven for packing up the car, queuing up “All Too Well,” and booking it there for the stunning fall foliage alone. But the small town ticks all the Vermontcore boxes: scenic hikes, a quaint main drag, Norman Rockwell-worthy accommodations (like the Woodstock Inn & Resort), a vibrant farm-to-table scene, and maple syrup-infused everything. Of course, you could also forget all those things and just follow the Vermont Cheese Trail — but, warning, you’ll never look at grocery store Cheddar the same.
🍂 Does involuntarily repeating “ooh, look at that one” count as an activity? It does in Woodstock, where every fall adventure comes with a side of red- and gold-dappled trees. Like a visit to Marsh-Billings-Rockefeller National Historical Park, where you can hike more than 20 miles of trails, including to Mount Tom’s roughly 1,360-foot-tall peak (well worth the panoramic views).
Looking for something less strenuous? Take a quick drive to Quechee State Park to walk along the 165-foot-deep gorge — dubbed “Vermont’s Little Grand Canyon.” Or, pop by one of the many local farms: Sugarbush Farm is known for its maple syrup production, while Billings Farm & Museum is popular for its Jersey cows and cheeses.
🖼 Live out your Gilmore Girls fantasy, with a day wandering around Woodstock’s cute-as-a-button downtown. Start at The Green, where you can admire textbook New England homes and buildings (see: what may be the world’s most charming library) and cross the idyllic Middle Covered Bridge.
After that, hit bustling Central and Elm streets to purchase foliage photos slightly more professional than the hundreds in your camera roll, flip through new releases at The Yankee Bookshop, and browse everything from puzzles to penny candy at F.H. Gillingham & Sons, a 140-year-old general store. Finally, you are in Vermont, so it’s practically state law to buy something plaid (preferably from The Vermont Flannel Co.) and enjoy a maple creemee — no matter how cold it is.
🧀 Look, if you want to drink maple syrup for breakfast, we’re not going to stop you. But you’ll probably prefer it poured over the challah French toast or steel-cut oatmeal at local institution Mon Vert Cafe. In the evening, have dinner at farm-to-table favorite Santé, followed by a nightcap at Au Comptoir, an auto shop turned chic cocktail bar. And if you also think visiting the local market is a key part of any trip, don’t leave town without swinging by the Woodstock Farmers’ Market to load up on personal-size pumpkin cheesecakes and — why not? — more cheese.