Weekend Getaway: Woodstock, Vermont in Winter
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There’s nothing quite as magical as a winter weekend in Vermont, and while there are lots of adorable towns worth visiting, a stroll through the historic town of Woodstock in the winter is like walking right into a snow globe!
So is Woodstock worth a winter trip? Yes. Plan a Friday to Sunday weekend, when the hours of every stop in this itinerary line up, and if you want snow on the ground and the holiday lights without Christmas-week crowds, come in January.
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.
Here’s a bite-sized snapshot of everything you need to know to plan your trip!
Table of Contents
Woodstock, Vermont in Winter at a Glance
- When to go December through March. January is the snowiest month, averaging about 23 inches.
- Best days Friday through Sunday, when the hours of every stop in this itinerary line up. Several restaurants close Monday to Wednesday.
- Where to stay The Shire Woodstock is walkable to the village and allows up to two dogs for an extra fee.
- Getting here About 2.5 hours from Boston and 4.5 hours from New York City. The closest airport is Lebanon Municipal (LEB) in New Hampshire, about 25 minutes away, with Cape Air flights from Boston and White Plains.
- Getting around The village is walkable. You’ll want a car for exploring Quechee and other nearby towns.
- Top 3 highlights Hiking or skiing Mount Tom, the animals at Billings Farm & Museum, and wandering Woodstock Village.
- Dog-friendly? Yes, with a little planning. Leashed dogs are welcome on Mount Tom’s free multi-use trails, and The Shire and the Woodstock Inn take dogs. VINS and the Village Inn do not.
Last checked by Tara: [October 2026]
Tara’s take
Woodstock or Stowe for Christmas? Woodstock, every time. It’s a storybook town, and while it’s still very busy in December, you don’t get the ski traffic you get in Stowe. Plus, the independent shops make Christmas shopping a pleasure, not a chore.
If you have a few days to escape to Vermont this winter, add Woodstock and its neighbor, Quechee, to your travel list.
We’ve been escaping to Woodstock and Quechee for many years, but it took us a while to try Woodstock in the winter. We’ve since remedied that situation, and we’ve been back several times on day trips, so here’s our itinerary for a perfect weekend with the best things to do in Woodstock, Vermont, in the winter.
What’s Open When in Woodstock This Winter
Plan your weekend for Friday through Sunday, and you’ll find every stop in this itinerary open. Here’s the week at a glance.
| Stop | Thu | Fri | Sat | Sun | Mon–Wed |
|---|---|---|---|---|---|
| F.H. Gillingham & Sons | 8:30 am–5 pm | 8:30 am–5 pm | 8:30 am–5 pm | Closed | 8:30 am–5 pm |
| Farmer & the Bell | 8 am–3 pm | 8 am–3 pm | 8 am–3 pm | 8 am–3 pm | Closed |
| Skinny Pancake (Quechee) | 7 am–3 pm | 7 am–3 pm | 7 am–3 pm | 7 am–3 pm | 7 am–3 pm |
| Mon Vert Cafe | Closed | 7:30 am–5 pm | 7:30 am–5 pm | 7:30 am–5 pm | 7:30 am–5 pm |
| Worthy Kitchen | 4–9 pm | 4–9 pm | Noon–9 pm | Noon–8 pm | Closed |
| Oakes & Evelyn | 5–9 pm | 5–9 pm | 5–9 pm | Closed | Tue–Wed only |
| Simon Pearce (Quechee), dinner | 5–8 pm | 5–9 pm | 5–9 pm | 5–8 pm | Wed only |
| Billings Farm & Museum | Select days | Select days | 10 am–4 pm | 10 am–4 pm | Select days |
| VINS Nature Center (Quechee) | 10 am–5 pm | 10 am–5 pm | 10 am–5 pm | 10 am–5 pm | 10 am–5 pm |
Open every day, free: the multi-use trails up Mount Tom (daylight hours, leashed dogs welcome), the covered bridges, and Quechee Gorge. Dogs: none of the restaurants allow them inside in winter, so plan meals around your pups if you bring them.
Day 1: Check into Your Lodging and Explore the Village of Woodstock
Where to Stay in Woodstock, Vermont in the Winter
There are so many places to stay in Woodstock and Quechee. Fair warning, though: 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.
Splurge
The Woodstock Inn & Resort
This stately inn has a spa, luxurious rooms, and a fine-dining restaurant. It’s a great spot for an anniversary splurge!
- Right downtown, on the village green
- Indoor pool and hot tub at the Athletic Club down the road (free shuttle)
- Runs the Woodstock Nordic Center
- Dogs: Yes, in limited rooms. Up to 2 dogs (100 lb combined), $150 per night
Victorian elegance
The Village Inn of Woodstock
Beautifully pink on the outside, with beautifully appointed rooms (some with fireplaces), and an easy walk to everything downtown.
- 41 Pleasant Street, walking distance to the village
- Breakfast is included in your stay
- Dogs: No (service animals only)
Tara’s pick
The Shire Woodstock
Look, I’m not saying The Shire is inexpensive, but it is less expensive than many of the other Woodstock hotels we’ve stayed in.
- On the river, across the street from the Village Inn
- Walking distance to downtown
- Dogs: Yes, up to about 40 lb. $50 per pet per night plus a $150 cleaning fee
Vacation rental
The Old Quechee Library
The most unique Airbnb I’ve stayed in for a long while: a cute brick rental that was once the Quechee Library, with a clawfoot tub and a fireplace.
- Walk to Simon Pearce and the Quechee Covered Bridge
- The drive to Woodstock is about 15 minutes.
- Dogs: Yes
Once you get settled at your accommodation of choice, it’s time to explore the village of Woodstock.
From the center of town, you can meander around several blocks of beautiful historic homes, festive holiday decorations, and incredible shops and restaurants. We recommend taking the afternoon to get the lay of the land and poke around in the shops.
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 at Vermont’s oldest same-family-operated general store, circa 1886. This cool shop has several rooms full of useful stuff, from dog toys and treats to craft beers, plus cosmetics, groceries, kitchenware, maple syrup samplers, and local crafts.
Clover Gift Shop: Right next door to F.H. Gillingham, the tiny Clover Gift Shop is jam-packed with gorgeous gifts 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. 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 downtown, 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 traditional pottery-making.
Dinner at Oakes & Evelyn
For your first night in Woodstock, we recommend a total foodie experience. We’ll save the burger joint for tomorrow.
The dinner spot I’m most excited about these days is Oakes & Evelyn, which opened in 2025 in The Jackson’s dining room on Senior Lane. Chef and owner Justin Dain already has a following in Montpelier, where the original Oakes & Evelyn opened in 2021.
The Woodstock location brings the same local, seasonal approach to the table, with small and large plates, raw seafood crudos, and several vegetarian and vegan options, which I always appreciate.
Dinner is served Tuesday through Saturday from 5 to 9 pm, so it fits nicely into a Friday night arrival. Call 802-233-4705 to reserve a table, and save room for dessert.
Day 2: Get Outside and Explore Winter in Woodstock, Vermont
If you’re staying in Quechee, start your day with indulgent crepes at the Skinny Pancake. If you’re in Woodstock, head over to the Farmer and the Bell or the best donuts you’ll ever have the pleasure of tasting. Seriously. (It’s open Thursday through Sunday, 8 am to 3 pm.)
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 Woodstock winter weekend.
If you love cross-country skiing or want to learn, Woodstock is one of the best places to try it.
Hike Mount Tom or Ski the Nordic Trails
The Woodstock Inn & Resort grooms the Nordic ski trails in Marsh-Billings-Rockefeller National Historical Park (Vermont’s only national park) and the trails on Mount Peg. There are miles of groomed trails, and many of them are perfect for beginners. More challenging trails are also available for experienced skiers.
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 day’s trail pass. You can also use the trails for snowshoeing if you want to go at a slower pace.
Finally, if you’d rather go for a snowy walk in the woods, about four miles of multi-use trails in the national park, including the carriage road up Mt. Tom, are open all winter (and free). Park in the lot shared with Billings Farm & Museum, just off Route 12, and walk in on the paved path by the flagpole.
Dogs are welcome on a leash, but you have to give skiers the right of way, stay out of the ski tracks, and pack out whatever your pup leaves behind.
As you walk, you’ll see numerous side trails. These are for skiers and snowshoers who have purchased a trail pass and aren’t available to walkers and hikers.
I hiked Mount Tom 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 Woodstock restaurants for lunch, from the mundane to the upscale, and Mon Vert is still my favorite.
They source their ingredients from local farms and bakers and make everything fresh to order. They also use Red Hen Baking Co. bread, my favorite in all of Vermont! Mon Vert gets really busy at noon, so if the stars align, go a tad earlier or later.
Read Next: 10 Perfect Things to Do in Woodstock in the Fall
Take a Winter Covered Bridge Tour
If you’ve read my post about fall in Woodstock, this might sound familiar. I love checking out covered bridges in Vermont, so yeah, I’ll probably 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. Parking is easy, and there are great spots for photos. It’s especially lovely at sunset.
Covered Bridges Near Woodstock Map
If you want to explore all six covered bridges within an easy drive of Woodstock, here’s a map you can use. This is a great little Woodstock road trip for photographers or anyone who wants to explore a bit of quintessential Vermont.
Dinner at Worthy Kitchen
I told you we were saving the burger joint for today, but this isn’t your average 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.
If you come in with a healthy appetite, you’ll leave 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.
Worthy Kitchen is located on Route 4, just east of downtown Woodstock, and is open Thursday and Friday from 4 to 9 pm, Saturday from noon to 9 pm, and Sunday from noon to 8 pm. It’s closed Monday through Wednesday, so plan your burger night accordingly.
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 adorable farm animals, taking a winter sleigh ride, or just meandering around a beautiful farm, make time for a visit.
Billings Farm & Museum opened in 1983 to preserve the historic Billings Farm, as well as the character and heritage of rural Vermont.
From November through February, Billings Farm is open on weekends and select days from 10 am to 4 pm, and starting in March, it’s open Friday through Monday. Special events are scheduled throughout the winter, so check the website before planning your trip.
Special events are scheduled throughout the winter, so 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 Skinny Pancake and visited the Quechee Covered Bridge, but we have 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 the Vermont Institute of Natural Science (VINS): 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.
Christmas in Woodstock: Wassail Weekend
If you happen to be visiting Woodstock during the second weekend in December, you’re in for a treat! In 2026, Wassail Weekend runs December 11-13.
Locals and visitors have gathered for this for more than 40 years, and it could easily be a scene from your favorite Hallmark movie, minus the big-city executive who falls for the Christmas tree farmer.
Ride in horse-drawn carriages, take part in craft workshops, sing Christmas carols, visit with Santa, and enjoy stories, theater performances, and live music.
Over at Billings Farm, you can watch the orchard get wassailed, an old custom of singing to the apple trees, then warm up by the fire pits with hot spiced cider. Visit Woodstock, Vermont, for the complete event schedule.
Should you spend Christmas in Woodstock or Stowe? I vote Woodstock. It’s a storybook town, and while it still gets very busy in December, you don’t fight the ski traffic you get in Stowe. I also love doing my Christmas shopping in Woodstock’s independent shops. Of course, my wallet is less of a fan, but holiday shopping always puts a dent in it, so I might as well support the locals.
Check out even more Vermont events in December!
Woodstock, Vermont Winter Travel Tips
Woodstock, Vermont, is probably one of the state’s most touristy towns, but winter is slower than other times of year, and lodging prices are lower, too!
Here are a few tips for planning your winter getaway in Woodstock, Vermont.
Plan everything in advance: Make restaurant reservations and check the day’s calendar for activities at Billings Farm and VINS. For the outdoor stuff, you can be a little more spontaneous. Hey, maybe that’s why I love getting outside!
Check out the Woodstock, Vermont website: It is a fantastic site and blog with lots of info on where to sleep, shop, and eat, plus special events happening around town.
What to Pack for a Woodstock Winter Weekend
- Your woolies. Merino wool clothing is awesome for winter layering, and it takes you from the hiking trail to dinner without complaint! I get my woolies from Ibex, and I’m never disappointed. Shop Ibex
- A packable puffy. This puffy jacket from Stio is so warm and light you barely notice it! See it at Stio
- Sturdy boots. Slushy snow makes walking in anything but boots a nightmare. Wear sturdy hiking boots, or better yet, insulated hiking boots for most of your Woodstock adventures. Shop insulated boots at REI
- Microspikes. I wore mine on Mount Tom, where you’ll share the trail with skiers and snowshoers. Get them at REI
Woodstock in Winter FAQ
Is Woodstock, Vermont worth visiting in winter?
Yes. The village keeps its holiday lights up well into February, lodging costs less than in foliage season, and you can ski, snowshoe, or hike Mount Tom right from town. Plan a Friday-to-Sunday trip, since several restaurants close early in the week.
Does Woodstock, Vermont get snow?
Yes. Woodstock averages about 82 inches of snow a year, and January is the snowiest month at about 23 inches (1991 to 2020 normals). December and February each average about 17 inches.
How cold does it get in Woodstock in winter?
January is the coldest month, with an average high of 29°F and an average low of 6°F. December averages a high of 34°F and a low of 14°F, so pack layers and insulated boots.
When is Wassail Weekend in 2026?
Wassail Weekend runs December 11 to 13, 2026. Billings Farm & Museum celebrates with wassailing in the orchard, farmhouse tours, and horse-drawn rides on select days, weather permitting, while the village hosts [parade and event details from woodstockvt.com].
Is Woodstock, Vermont dog-friendly in winter?
Mostly. Leashed dogs are welcome on the free multi-use trails up Mount Tom (I keep mine leashed the whole way, since skiers and snowshoers share the trail), and The Shire Woodstock and the Woodstock Inn both accept dogs for a fee. VINS doesn’t allow pets past its admissions area, and the Village Inn of Woodstock doesn’t take pets.
Do you need a pass to hike Mount Tom in winter?
Not for walking. About four miles of multi-use trails in Marsh-Billings-Rockefeller National Historical Park, including Mount Tom Road and the Pogue Loop, are free. Skiing or snowshoeing on the groomed trails requires a pass from the Woodstock Nordic Center.
Read Next: The Best Winter Getaways in Vermont
Your perfect winter weekend in Woodstock awaits! Pack your bags and plan your trip to this gorgeous little town!
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