Woodstock, Vermont: The Essential Guide

Woodstock, Vermont, is a cute town located 30 minutes west from Lebanon, New Hampshire. There’s nothing I enjoy more as the fall season approaches than visiting a place that smells of maple syrup and mulled apple cider. 

I’ve been traveling north. New York City Since I was a child, I have been moving from Boston to Vermont. Since I am a mother, the Green Mountain State became our little retreat. 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. Airbnb reported recently that Vermont was the most popular destination for travelers. top-rated fall foliage destination by Airbnb guests. 

I love to talk with the thousands of visitors that we get. “Most have never seen foliage, and they love our beautiful town in Vermont,” says Elizabeth Finlayson. Finlayson says that the town, which has just 3,000 people living there, receives an average of 23,800 monthly visitors during 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.

What you need to know about Woodstock, Vermont before planning your trip. 

Best Hotels & Resorts

Woodstock Inn & Resort

A little further away from Woodstock Green, you’ll find the Woodstock Inn & Resort. Rooms range from those that look out onto the gardens of the inn to the Laurance S. Rockefeller Suite, which has hand-painted murals as well as a cedar walk-in closet.

The hotel also has two restaurants. The Red Rooster You can also find out more about the following: Richardson’s TavernThe Vermont Bite uses locally-grown ingredients in both dishes. 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

The main road in Woodstock is only a short distance away. The Jackson It has a quiet historical charm, but also modern creature comforts. For example, it offers comfortable beds and upgraded bathrooms. The inn has three acres of peaceful grounds, including a fire pit, cute footbridge and a linden trees grove. Grab breakfast at the Farm-to-Table restaurant before heading out for the morning. Oakes & Evelyn.

Twin Farms

The resort is an adult-only all-inclusive with a wide range of treehouses and cottages. John Graham is the managing director at Twin Farms. “Woodstock is particularly magical in the autumn, with highlights like ShackletonThomas You can also find out more about the following: Stave Puzzles nearby.”

The Village Inn Woodstock

It’s a girl! It’s The Village Inn of WoodstockThis Victorian bed and breakfast is a vibrant pink and yellow. The stay is intimate, with only seven rooms. Each room has a fireplace and Victorian charm. The Vic Tavern It serves gastropub food, with a menu largely inspired from American and Asian cuisines.

The Best Things to do

Take a walk.

Finlayson suggests walking up. Mount Tom In the fall. The perfect way to see the fall foliage, get warm, and enjoy a bird’s-eye view 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

The Woodstock Inn & Resort is located just down the road. Kelly Way Gardens, the lush gardens that produce the property’s flowers and produce. You don’t need to be a hotel guest to appreciate the beauty of the gardens. Reservations are required for this culinary experience. farm-to-table program For a memorable dinner.

Billings Farm and Museum

The historic zoo is full of cute animals. Billings Farm and Museum. You can book a private wagon-ride or attend a fall-themed event here. Pecks, Pies & Spies: Apple Growing in Vermont The two-day Harvest Celebration This includes apple cider pressing and pumpkin bowling, as well as dancing on crunchy leaves. Visit their Farmhouse Scoop Shop for apple cider donuts, hot spiced cider, and pumpkin ice-cream. 

Sugar Bush Farm

Sugar Bush Farm The farm is celebrating its 80th year this year. It’s a perfect place to learn about maple syrup production, meet farm animals and satisfy your cheese addiction in just one visit. The farm is a Vermont cheddar specialist and sits on 550 acres with picturesque rolling hills. Feel like getting hitched? Sugar Bush Farm is a great place to get married. charming one-room chapel Nestled in the woods

Best Shopping

Unicorn

The shop opened in 1978 and has grown since then. Instagram Puts it simply Unicorn Specializes in everything “from the sublime to ridiculous.” Unicorn is owned by Jeffrey Kahn. Walking into Unicorn, you feel like there’s a surprise waiting on every shelf. It has a wide variety of items, including toys, colorful gems and raw polished stones, as well as funny wall art. 

“Transmitting joy” [through] Kahn says, “The diverse mix of Unicorn’s offerings rewards me in a spiritual way.”

The Yankee Bookshop

The small town cannot have a quaint main street Without a cute bookstore. Yankee Bookshop There are shelves full of guides, bestsellers and local authors. The children’s area is crammed with the fun items that kids enjoy. 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

Woodstock is a great place to visit if you want to step back in time. F. H. Gillingham & Sons. It is one of the oldest general stores in the State, with creaky wood floors and a lot of charm. You can get candy, kombucha and Vermont sweatshirts or soap all at once. The mini-candies are a favorite of my kids. Although they don’t cost a penny anymore, it is close enough to jazz.

Vermont Flannel Company

Woodstock is not complete without a wrap. 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.” You can also wear your flannel with shirts, pants and hair ties.

Best Restaurants

Oakes & Evelyn

Oakes & EvelynThe original restaurant is located in Montpelier in Vermont. But it is fortunate that the Woodstock location opened in 2025. This is the type of restaurant that locals and tourists alike dream about having right in their own backyard. The Jackson is located on the ground level and offers a variety of meals, including a breakfast buffet as well as seasonal dinners. The interior is light and airy. During the winter months, a stone fire place serves as an attractive centerpiece. I highly recommend the baos, which are stuffed full of local mushrooms.

Woodstock Farmers’ Market

Note to travelers: this isn’t the Green Market that runs from mid-October through the end of November (also called the Market on the Green). The Rather than Woodstock Farmer’s Market On Route 4 between Bridgewater, Vermont and downtown. 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. If you haven’t tried the personal-sized, creamy pumpkin cheesecakes, then you aren’t experiencing bliss.

Dreamscape Coffee

Here’s a great place to stop and relax in Woodstock after leaf peeping. This is the perfect place to take a break from leaf peeping in Woodstock. Dreamscape CoffeeYou can also enjoy locally sourced maple cinnamon “poptarts” or pumpkin bread with your creative drink. 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

My kids have been complaining about the lack of a good burrito place in Woodstock for years. We were thrilled to see the new shop. Ranch CampThis September, the restaurant opened. Tacos, beer, and burritos are the specialties of this restaurant and bike shop, which has its original location in Stowe in Vermont. There are plenty of vegan choices, including the veggie-filled Burritos or the fried artichokes. Meat lovers never fear—there are still hearty dishes like pork belly tacos to be had. 

Mont Vert Café

There will be a line for this popular and long-standing spot in Woodstock. But the wait is worth it. 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. If the weather in New England is nice, I suggest eating on the patio.

The Best Time to Visit

Woodstock can be visited at any season, but October to December is the best time for an authentic New England experience. The cold-season months Woodstock is home to some of the most popular annual events in Woodstock, including the Apples and Crafts and Food Truck FestivalThe event features over 100 food producers and vendors. There’s a Christmas market in December. Wassail WeekendA village celebration of winter with horse-drawn carriages, twinkling light, historic homes decorated, and holiday songs.

How to get there

Boston Logan International Airport, located in Boston, is the nearest major airport. From there, it takes a little more than two hours to drive into town. JetBlue and Cape Air operate regional flights between Boston and Lebanon, New Hampshire. Woodstock is a 30 minute drive from there.

How to Get Around

The area around Woodstock is not car-friendly, but it has some of Vermont’s most scenic roads. These include the Ottauquechee River in Taftsville and the Quechee Gorge – a mile-long, 165-foot deep canyon. The Quechee Gorge is a short detour that’s worth taking, especially if it has been raining recently. Simon Pearce In a restored 19th-century Vermont mill, there is a farm to table restaurant and a glassware store. The building overlooks a waterfall.