The Essential Guide to Woodstock, Vermont

30 minutes west of Lebanon, New Hampshire, is the cute-as-a-button town of Woodstock, Vermont. As the fall season ramps up, there’s nothing more fulfilling to me than visiting a place where the air is filled with the smell of mulled apples, maple syrup, and the crisp cool of autumn. 

I’ve been heading north from New York City and Boston to Vermont since I was a kid. Now, I have a family of my own, and the Green Mountain State has become our little escape. Each season has its perks—swimming in the summer and skiing in the winter—but it’s hard to deny that Vermont is particularly special in the fall. In fact, Airbnb recently reported that Vermont is the top-rated fall foliage destination by Airbnb guests. 

“I love talking to the thousands of visitors we have. Most have never seen foliage and love our beautiful town and Vermont in general,” says Elizabeth Finlayson, director of the Woodstock Area Chamber of Commerce. According to Finlayson, the town of just 3,000 residents sees a monthly average of 23,800 visitors in the fall.

While the influx of travelers can feel overwhelming at times, Finlayson feels lucky to call Woodstock her home, especially during the fall when the smell of wood stoves and leaves wafts through the air—and she loves to share that autumnal magic with visitors.

Here’s what to know before planning a trip to Woodstock, Vermont. 

Best Hotels & Resorts

Woodstock Inn & Resort

Across from Woodstock’s Green is the Woodstock Inn & Resort. The aesthetic here feels timelessly charming, and rooms range from options that overlook the inn’s gardens to the three-room Laurance S. Rockefeller Suite that has thoughtful details such as hand-painted murals and a walk-in cedar closet.

There are also two on-site restaurants, The Red Rooster and Richardson’s Tavern, both of which use locally grown ingredients to craft creative Vermont bites. Don’t forget to order the warm apple tarte tatin, which features pillowy pastry topped with creamy vanilla ice cream—it tastes exactly like fall.

The Jackson

A short distance from Woodstock’s main drag, The Jackson has quiet historic charm and modern creature comforts such as comfortable beds and updated bathrooms. The inn sits on three acres of peaceful grounds and has a fire pit, a cute foot bridge, and a linden tree grove. Before heading out for the day, grab breakfast at the farm-to-table restaurant, Oakes & Evelyn.

Twin Farms

This adult-only, all-inclusive resort has a variety of cottages and treehouses to choose from. “There is so much to enjoy in Vermont during the fall, and it truly comes down to the rhythm and feeling of the season,” says John Graham, managing director of Twin Farms. “Woodstock in the fall is especially magical, with highlights such as ShackletonThomas and Stave Puzzles nearby.”

The Village Inn of Woodstock

Who’s that girl in pink? It’s The Village Inn of Woodstock, a bright pink and yellow Victorian bed-and-breakfast. This stay is one of the most intimate in the area, with just seven snug rooms that lean into Victorian-era charm with in-room fireplaces. The Vic Tavern serves gastropub fare, and the menu is largely inspired by American and Asian cuisines.

Best Things to Do

Take a hike.

Finlayson recommends walking up Mount Tom in the fall. It’s the perfect way to enjoy the foliage, warm your body, and get a bird’s eye view of the town of Woodstock. Every night, between November and April, you will see a large star twinkling on the 1,357-foot-tall peak—it was originally installed in 1942 to welcome soldiers who were returning from World War II.

Red Barn Dinners

Down the road from The Woodstock Inn and Resort is Kelly Way Gardens, the bountiful gardens where the property’s produce and flowers are grown. However, you don’t have to be a guest to enjoy the beauty and bounty of the garden. Reserve a spot at this culinary farm-to-table program for a memorable and creative dinner.

Billings Farm and Museum

Yes, cute animals do indeed abound at the historic Billings Farm and Museum. Reserve a private wagon ride or attend one of its fall-themed (and tasty) events here, like Pecks, Pies & Spies: Apple Growing in Vermont or the two-day Harvest Celebration that includes activities like dancing on crunchy leaves, apple cider pressing, and pumpkin bowling. Make sure to stop by their Farmhouse Scoop Shop, which serves hot spiced cider and apple cider donuts alongside pumpkin ice cream. 

Sugar Bush Farm

Sugar Bush Farm is celebrating its 80th birthday this year, and it’s the perfect place to visit farm animals, learn how maple syrup is produced, and nourish your cheese addiction all in one visit. The farm specializes in Vermont cheddar and is set on 550 acres of picture-perfect rolling hills. Feel like getting hitched? Sugar Bush Farm has a charming one-room chapel nestled in the woods.

Best Shopping

Unicorn

This special shop has been open since 1978, and as its Instagram puts it, Unicorn specializes in everything from the “sublime to the ridiculous.” Owned by local Jeffrey Kahn, walking into Unicorn feels like you may find a delightful surprise on every shelf. From colorful raw and polished gems, toys, and funny wall art, it really does have something for everyone. 

“Transmitting a sense of joy [through] the eclectic mix found at Unicorn ends up rewarding me spiritually,” Kahn says.

The Yankee Bookshop

A small town can’t have a quaint main street without a cute bookshop. Yankee Bookshop is stacked with shelves full of bestsellers, local authors, and guides. It also has a packed children’s section stocked with all the fun knick-knacks kiddos love. And things are about to get even better for Yankee—the bookshop recently expanded and has plans to develop the new space into a place to hold book events.

F. H. Gillingham & Sons

There’s no better way to go back in time while visiting Woodstock than by visiting F. H. Gillingham & Sons. Known as one of the oldest family-run general stores in the state, it has creaky wooden floors and plenty of old-fashioned charm. While here, you can pick up some candy, kombucha, Vermont-themed sweatshirts, or a bar of handmade soap, all in one stop. My kids especially love the mini-candies. Though they no longer cost a penny, it’s close enough for jazz.

Vermont Flannel Company

You can’t visit Woodstock without wrapping yourself in one of The Vermont Flannel Company‘s blankets. I have two of the stadium blankets—one side is flannel and the other is fleece—and as the company states, they are “brushed beyond reason for ultimate softness.” If you prefer to wear your flannel, you’ll also find shirts, pants, and even hair ties made with the company’s silky smooth fabric.

Best Restaurants

Oakes & Evelyn

Oakes & Evelyn‘s original location is in Montpelier, Vermont, but it’s lucky that the restaurant opened its Woodstock outpost in 2025, because this is the kind of restaurant that both locals and tourists dream about having in their backyard. Located on the ground floor of The Jackson, it has a hearty breakfast menu as well as a seasonally inspired dinner menu. The space is bright and airy, and during the colder months, the stone fireplace serves as a cozy centerpiece. I recommend ordering the bao buns; they are stuffed with local mushrooms.

The Woodstock Farmers’ Market

Travelers take note: This isn’t the farmer’s market that takes place on the Green through mid-October (also known as the Market on the Green). Rather, the Woodstock Farmer’s Market is on Route 4 between downtown and Bridgewater, Vermont. Inside, you’ll find local produce and meat, a deli with premade sandwiches and meals, a coffee bar, and my absolute favorite spot—the pastry case. You haven’t experienced bliss until you’ve had one of the creamy, personal-sized pumpkin cheesecakes.

Dreamscape Coffee

This is the perfect place to take a break from leaf peeping in Woodstock. At Dreamscape Coffee, you can enjoy a locally-sourced maple cinnamon “poptart” or pumpkin bread alongside creative drinks. I recommend the Pumpkin King, a quintessential pumpkin spice latte, and the Harvestide, which has notes of brown sugar and warm pecan—it’s basically pecan pie in a cup.

Ranch Camp

For years, my kids lamented the lack of a proper burrito shop in Woodstock, so we were all giddy over the new Ranch Camp, which opened this September. The restaurant and bike shop (which has an original location in Stowe, Vermont) specializes in tacos, burritos, and beer. The menu is famously gluten-free, and there are also plenty of vegan options, such as the fried artichokes or the veggie-filled burritos. Meat lovers never fear—there are still hearty dishes like pork belly tacos to be had. 

Mont Vert Café

This is a longstanding and very popular spot in Woodstock, so prepare yourself for a long line. However, the wait for a Mont Vert Café meal is more than worth—the restaurant isn’t lying when it says its food is “fresh and local.” As a native New Yorker, I love the Lox & Shmear, while my midwestern husband favors the Coffeehouse Brisket, which has coffee-marinated, locally sourced brisket served with pickled red onions, basil aioli, Swiss cheese, and veggies on a baguette. When the New England weather cooperates, I recommend taking your meal on the patio.

Best Time to Visit

Woodstock can be enjoyed in all seasons, but plan to visit anytime from October through December if you want the true New England experience. The cold-season months see some of Woodstock’s most popular annual events, such as the Apples and Crafts and Food Truck Festival, which has over 100 vendors, food producers, and food trucks. In December, there’s Wassail Weekend, a village winter celebration with horse-drawn wagons, twinkling lights, decorated historic homes, and holiday music.

How to Get There

The closest major airport to Woodstock, is Boston Logan International Airport (BOS), and from there it’s a little over a two-hour drive to town. A few airlines, such as JetBlue and Cape Air, operate regional flights from Boston to nearby Lebanon, New Hampshire. From there, it’s just a 30-minute drive to Woodstock.

How to Get Around

While cars are required for getting around, the area in and around Woodstock has some of the most beautiful roads you will experience, which are peppered with things like bucolic farms, the Ottauquechee River, a covered bridge in Taftsville, and the Quechee Gorge, a 165-foot-deep, mile-long canyon, and the deepest gorge in Vermont. A short detour worth taking (especially if there’s been a recent rain), is Simon Pearce a glassware shop and farm-to-table restaurant in a restored 19th-century mill that overlooks a waterfall in nearby Quechee, Vermont.