It’s hard to play favorites in New England, but Vermont is at the top of my list. It’s pretty wild to think when I first wrote this travel guide three years ago I only dreamed of living there one day. I will never forget hopping on bikes while staying at the Woodstock Inn and riding through town. Craig and I stopped on a little side street, looked at each other and said “we need to live here.” We are usually always ready to head home at the end of a trip, but Vermont was different.
Driving along winding country roads, passing farms and covered bridges, it’s a place that feels suspended in time. It felt like home. Forget strip malls, big chain stores, and billboards, what you’ll find in and around Woodstock is good old New England charm. Not only is it absolutely beautiful but the people are the ones that make Vermont special. Incredibly friendly, warm and welcoming, Vermonters greet you with kindness and a sense of community.
Visit in the fall for the most spectacular shows of fall foliage, come in the winter for snow covered bridges and cozy days by a fire, or visit in the summer for lake swimming and lush green mountains. No matter the season, there’s plenty to enjoy. Here are some of my favorite things to do, places to stay, and where to eat when visiting Woodstock, VT.
*A general note. State regulations and recommendations are constantly changing and evolving due to Covid-19. Please follow all state and local mandates when traveling and enjoying time in Woodstock and the state of Vermont.
Woodstock Travel Guide
Where to Stay
Our first visit we stayed at the Woodstock Inn which is one of the main reasons we fell in love with Woodstock (book with this link to get 10% off your stay until 12/24/22-holidays are blacked out). You can’t beat the location which is set right in the heart of Woodstock, easily walkable to everything in town. The rooms are comfortable and charming, and they have several that are pet friendly! There are several dining options on site, but if you happen to be visiting when Kelly Way Gardens is open it’s a must see. It’s a farm to table dinner that Craig and I had the chance to experience in September a few years ago. The meals are all created with food grown at the Gardens or local farms and the entire property and space is beautiful.
The Woodstock Inn also has an incredible list of amenities.
The spa is not surprisingly one of the most popular. I’ve had the opportunity to do several treatments and a mani/pedi and they were all wonderful. There’s also a heated outdoor saltwater pool for the summer months at the hotel. There’s an indoor pool at the Athletic Club open to Inn guests. The Athletic Club is an amazing facility with indoor tennis courts, a gym, outdoor tennis courts, fitness classes, sauna and steam room. It’s my favorite place in the winter months for tennis and swimming. Not far from the Woodstock Inn is the Woodstock Country Club a phenomenal course designed by Robert Trent Jones. In the winter months it turns into a nordic skiing and fat biking track.
Woodstock Inn also offers a fly fishing program for guests. There’s truly so much to do in and around Woodstock. Skiing and snowboarding in the winter is so fun, with two mountains 15-20 minutes from the hotel. I can’t say enough good things about the Woodstock Inn (book with this link to get 10% off your stay until 12/24/21-holidays are blacked out).
If you’re looking for a rental, we stayed at this house on Silver Lake (about a 15 minute drive to Woodstock) and it was wonderful. You can rent the entire house or the main level upstairs and the downstairs apartment. It’s pet friendly too!
What to Do (Top 20 Things To Do In Woodstock)
There really is no shortage of things to do in Woodstock. If you’re staying at the Woodstock Inn they provide plenty of bicycles to ride around town. There is plenty of great shopping and sightseeing which is all easily walkable. Whether you’re shopping, strolling, headed to the spa or going on an outdoor adventure I can guarantee you will not be bored. If you scroll all the way to the bottom, I’ve noted some kid and dog friendly activities and excursions as well as some upcoming fun events in Woodstock. I’ll update these seasonally!
Farmhouse Pottery – The famous Farmhouse Pottery (as seen all over my house and kitchen, lol). Their shop and studio is a must see!
FH Gillingham & Sons – A Woodstock staple, part general store, part gift shop, they have a little bit of everything
Clover Gift Shop – Cute local gift shop with everything from blankets to candles and tea towels.
The Yankee Bookshop – Adorable book shop right in the center of town.
Woody’s Mercantile – Fun unique items and gear.
Hikes & Activities
Mt. Tom – There are a few different trail options to hike to the top. We did the Faulkner trail but there were some detours (clearly marked). The park at the bottom (Faulkner Park) is dog friendly on leash.
Suicide Six – Mountain Biking, Skiing/Snowboarding
Mt. Peg Trails – Mountain Biking, Hiking, Nordic Track/Snowshoe/Fat Bike in winter, no dogs during winter months
Marsh Billings National Park – Across the street from Billings Farm. Lots of great hikes, dogs allowed on leash.
Sugarbush Farm – Cheese and maple syrup farm.
VINS Nature Center – A nature center with raptors and songbirds, nature trails and a forest canopy walk.
Where to Eat
Mangalitsa – One of the best meals we’ve ever had. Farm to table. Intimate dining experience. Reservations only (we got SO lucky and got a table as walk-ins, it was 5pm).
Village Butcher – The BEST sandwiches we LOVE their Veggie Lover’s Delight. Grab it to go and eat it at Faulkner Park (there’s only one picnic table) or walk to East End Park and sit on the Ottaqueechee River (lots of picnic benches).
Mon Vert Cafe – Great spot for coffee, pastries, breakfast sandwiches, and lunch. Outdoor seating available.
Worthy Kitchen – Farm to table comfort food. It gets really busy, go early if you can. Outdoor seating available on their porch and you can also get takeout and sit at their picnic tables under the trees.
The Ransom Tavern at Kedron Valley Inn – So cozy and quaint. Yummy menu and fun cocktails. Outdoor seating available.
South Woodstock Country Store – Serving breakfast and lunch. Yummy sandwiches, salads and baked goods.