The Fairytale Town in Vermont You Have to See in the Winter
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When the snow starts to fall across New England, my thoughts turn, not to skiing, but to simpler adventures. Cozy towns with twinkling lights. Hot drinks by a cozy fire. Cute shops with one-of-a-kind treats.
While there are dozens of adorable towns in Vermont worth visiting, a winter stroll through the historic town of Woodstock is like walking right into a snow globe!
The winter holidays in Woodstock are magical, but even if you visit in February, the decorations continue to light up the town for a bit of winter cheer. Restaurants and shops line the downtown streets, and beautiful, historic homes and buildings surround the town.
If you have a few days to escape to Vermont this winter, put Woodstock and its neighbor, Quechee, on your travel list.
We’ve been escaping to Woodstock and Quechee for many years, but until this year, we’d never been to Woodstock in the winter.
I’m happy to say that we’ve recently remedied that situation, and we’ve created an itinerary for your perfect weekend with the best things to do in Woodstock, VT, in the Winter.
Day 1: Check into Your Lodging and Explore the Village of Woodstock
Where to Stay in Woodstock
There are so many places to stay in Woodstock and Quechee. Fair warning – this is an expensive area, so you’re more likely to find posh inns and B&Bs than you are roadside motels. Here are some recommendations for the best hotels in Woodstock, Vermont, from luxurious to more budget-friendly.
For total luxury: The Woodstock Inn & Resort is located right downtown. This stately inn features a beautiful spa, luxurious rooms, an indoor pool, and a fine-dining restaurant. It’s a great spot for splurging on an anniversary stay!
For Victorian elegance: The Village Inn of Woodstock is beautifully pink on the outside, and the interior features luxurious rooms with fireplaces. It’s located within walking distance of everything downtown Woodstock has to offer.
For budget accommodations: Look, I’m not saying The Shire Woodstock is inexpensive, but it is less expensive than many of the other Woodstock hotels we’ve stayed in. This motel is located right across the street from the Village Inn and within walking distance of downtown.
Once you get settled at your accommodation of choice, it’s time to explore the village of Woodstock.
Explore Woodstock Village, Vermont
Here are some of the unique shops in Woodstock that we love to visit when we’re in town:
- F.H. Gillingham & Sons: Step back in time to the oldest general store in Vermont, circa 1886. This cool shop features several rooms full of useful stuff, from dog toys and treats to craft beers, not to mention cosmetics, groceries, kitchenware, maple syrup samplers, and local crafts.
- Clover Gift Shop: Right next door to F.H. Gillingham is the tiny Clover Gift Shop, which is jam-packed with gorgeous gift items from local artisans, including hand-poured candles, pottery, cards, CBD products, and upscale cosmetics. Browsing here is an experience!
- Unicorn: Featuring novelty gifts, cards, puzzles, games, and toys. This is a fun store to get lost in!
- Vermont Eclectic Company: Unique Vermont clothing created by local artists. We love their cool designs.
- Farmhouse Pottery: Located outside of the downtown area, Farmhouse Pottery is an iconic pottery studio, gift shop, and kitchen store. You can even book a clay date and work alongside a master potter to learn about traditional pottery making.
Dinner at The Prince & The Pauper
For your first night in Woodstock, we recommend a total foodie experience. We’ll save the burger joint for tomorrow.
One of the most renowned restaurants in Woodstock is the Prince & the Pauper on Elm Street, right downtown. Yes, you have to make reservations, but you’ll be treated to a fantastic meal in the coziest of spaces.
Keep it simple and choose the three-course Prix Fixe menu, which includes an appetizer, salad, and entrée.
Day 2: Get Outside and Explore Winter in Woodstock, Vermont
Now, it’s time to enjoy winter in Vermont with some outdoor activities. From hiking and snowshoeing to Nordic or downhill skiing and horse-drawn sleigh rides, there are dozens of ways to get outside during a winter weekend in Woodstock.
If you love cross-country skiing or are interested in learning how to do it, Woodstock is one of the best spots to give it a go.
The Woodstock Inn & Resort grooms the Nordic ski trails in Marsh-Billings-Rockefeller National Historical Park (Vermont’s only national park unit) and the trails on Mount Peg. There are 45 km of trails, and many of them are perfect for beginners. There are a few more difficult trails for experienced skiers, too.
If you are new to the sport, head over to the Woodstock Nordic Center at 76 South Street in Woodstock. This is the spot to rent equipment, sign up for a lesson, and buy your trail pass for the day. You can also use the trails for snowshoeing if you want to go at a slower pace.
Finally, if you’d rather just go for a snowy walk in the woods, the multi-use trail up to the top of Mt. Tom is free to use in the winter. Park in the main lot at Billings Farm & Museum and cross the road to get on the trail system. Dogs are permitted, but you have to give skiers the right of way and stay on the side of the trail.
As you walk, you’ll see numerous side trails. These are for skiers and snowshoers who have purchased a trail pass and can’t be used by walkers and hikers.
I did this hike with my dogs and saw maybe four skiers the whole time I was out. The snowy woods in Vermont should be experienced by everyone, and these trails are perfect for families.
Read Next: Trail Guide for Mount Tom and the Pogue in Woodstock, Vermont
Lunch at Mon Vert Cafe
Located on Central Street in downtown Woodstock, Mon Vert Cafe is the place for great coffee, wraps, and sandwiches. I’ve tried a bunch of different Woodstock restaurants for lunch, from the mundane to the upscale, and Mon Vert is still my favorite spot.
They source their ingredients from local farms and bakers and make everything fresh to order. It helps that they use Red Hen Baking Co. bread, my favorite in all of Vermont!
Read Next: 10 Perfect Things to Do in Woodstock in the Fall
Take a Winter Covered Bridge Tour
For those of you who have read my post about fall in Woodstock, this might sound familiar. I love checking out covered bridges in Vermont, so yeah – there’s a good chance I will include at least one covered bridge visit in any Vermont itinerary.
There are a bunch of covered bridges in and around Woodstock, and Middle Covered Bridge is located right downtown. You can tour all of them in an afternoon, but if you are less excited about covered bridges, at least head over to my favorite, the Taftsville Covered Bridge, built in 1836.
The Taftsville Covered Bridge is located right on Route 4 in the village of Taftsville, Vermont, which is part of Woodstock. There’s easy parking and good spots to take photos. It’s especially lovely at sunset.
Dinner at Worthy Kitchen
I told you we were saving the burger joint for today, but this is no ordinary burger joint. Worthy Kitchen in Woodstock, Vermont, is an iconic eatery known for fabulous burgers, local craft beers, and donuts. This is comfort food done right, and it’s sure to impress, even if you’re visiting with kids in tow.
Save lots of room for your meal at Worthy Kitchen; even the veggie burger is divine. Alas, their fries aren’t vegetarian, but I hear they’re delicious all the same.
As long as you enter with a healthy appetite, you’ll leave this place happy. Oh, if you’re visiting on a weekend, you should probably make a reservation just to ensure you get the Worthy burger you deserve.
Day 3: Billings Farm & Museum
Billings Farm & Museum is a working farm and non-profit organization on 200 acres in Woodstock, Vermont. If you’re interested in learning more about farm life, meeting some adorable farm animals, taking a winter sleigh ride, or just meandering around a beautiful farm, you have to make time for a visit.
The farm was established as a nonprofit in 1983 to preserve the historic Billings Farm, as well as the character and heritage of rural Vermont.
During the winter months, it is only open on weekends unless you visit during Vermont’s winter vacation week in February, when it’s open every day from 10 am to 4 pm.
Special events are scheduled throughout the winter, so be sure to check the website before planning your trip.
Pay a Visit to Nearby Quechee, Vermont
Maybe, like us, you’ve chosen to hang your hat in nearby Quechee, Vermont, during your winter weekend in Woodstock.
Quechee is a small community well worth checking out if you have time. If you’re staying in town, you’ve probably already eaten at the Skinny Pancake and visited the Quechee Covered Bridge, but we’ve got a few more suggestions.
- Hike into Quechee Gorge: Called Vermont’s Grand Canyon by some, you can easily view Quechee Gorge from above by walking on the Route 4 bridge and looking down. If you want a closer view, hike into the gorge from the visitor center. It’s about 2.7 miles round-trip.
- Visit Simon Pearce for lunch/dinner: Simon Pearce Glassware has been handcrafted in Quechee, Vermont, since 1981. You can browse their collection in the flagship store, see a glassblowing demonstration, and dine on some of the finest food in Vermont.
- Visit Vermont Institute of Natural Science: VINS is a wildlife rehabilitation and nature center with a mission to motivate individuals and communities to care for the environment through education, research, and avian wildlife rehabilitation. The forest canopy walk gives visitors a cool perspective into the Vermont woods. You can also visit with the animals, check out the exhibits, and hike the trails.
Wassail Weekend in Woodstock
If you happen to be visiting Woodstock during the second weekend in December, you’re in for a treat!
Come see Woodstock transformed into a winter wonderland. Ride in carriages pulled by horses, take part in craft workshops, sing Christmas carols, visit with Santa, and enjoy a myriad of stories, theater performances, and live music.
Visit Woodstock, Vermont, for a complete schedule of events.
Your perfect winter weekend in Woodstock is waiting for you! Pack your bags and plan your trip to this gorgeous little town!
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