Winters in Woodstock are truly magical. Glistening snow, twinkling lights, cozy fireplaces, and a charming village. The picturesque village of Woodstock, makes the perfect winter getaway. Whether you are an adventure seeker or looking to relax and unwind, Woodstock has a little bit of something for everyone. Adventure abounds with everything from skiing, hiking and fat biking to more leisurely activities like shopping, dinning and luxurious spa treatments. You simply can’t go wrong. If you are traveling to Woodstock this winter, look no further. We are sharing the best of winter in Woodstock from a local perspective to ensure you get the most out of your time in this charming town.
You might also like: Where to Eat in Woodstock, Where to Stay in Woodstock, & Woodstock VT Shopping Guide. Head here for all the Vermont content your heart desires.
Our complete guide to your Woodstock getaway during the winter season.
Woodstock, VT Winter Itinerary
Lodging
The Woodstock Inn & Resort
The Woodstock Inn (book with this link for 10% off your stay) is one of the most convenient and luxurious spots to stay in Woodstock. Staying at the Inn during the winter is extra special with the cozy fireplace, common areas, restaurants, spa amenities and more. Not to mention it is located right in the village, just a few minutes from all the downtown shopping and dining you could imagine. Be sure to book your spa appointments and dining ahead of time.
506 On The River Inn
506 On The River Inn is a great family-friendly option with an indoor pool, game room and in-house restaurant for the whole family to enjoy. Located just a short drive outside the village this makes the perfect place to base your Woodstock stay, especially with little ones in tow.
Day One
Breakfast
Enjoy a delicious breakfast at Mon Vert Cafe located centrally in the village. This is a favorite spot for both locals and visitors serving up delicious, rustic, country food and strong coffee. They have yummy coffee specials and lots of cozy spots to enjoy your meal.
For a quick meal on the go, grab breakfast sandwiches, pastries and coffee from the Village Butcher!
Daytime Exploring
Acquaint yourself with the village by taking a brisk, wintery stroll around town. Be sure to bundle up and wear comfortable shoes. Walk across the Village Green, Middle Covered Bridge (don’t miss the view of the start lit up on the top of Mt. Tom as you approach the bridge), explore River Road, Mountain Ave. and Faulkner Park. Loop around to walk through the village and check out some of our favorite shops in downtown.
Stormy day/kid-friendly option: Head to the Woodstock Athletic Club, part of the Woodstock Inn & Resort amenities. If you aren’t staying at the inn you can still purchase day passes to use the gym, attend fitness classes and enjoy the pool, steam room, sauna, and whirlpool.
Lunch
For a classic Vermont experience, head to the South Woodstock Country Store just 10 minutes from the village. Enjoy a delicious sandwich, soup, or salad and don’t miss some sweet treats like their brownies and cookies.
If you’re looking for lunch on the go, head back to the Village Butcher for one of their delicious fresh made sandwiches. Choose from their classics or make your own! You can’t go wrong with fresh meats, breads and produce.
Afternoon Exploring
Spend your afternoon at the Nordic Center cross-country skiing, snowshoeing or fat biking. You can rent gear at the Nordic Center and even arrange for lessons. Trails range from beginner to advanced with a little bit of something for everyone. Enjoy a hot or cold beverage, soup and sandwiches at the Fairway Grill (the on-site restaurant) after your adventure!
Looking to cozy up indoors? Head to the Woodstock Inn Spa for an afternoon of relaxation. Choose from the delightful menu of winter seasonal spa treatments and enjoy the amenities, including the whirlpool, sauna and steam room. Not to mention, the cozy lounge and fireplace–the perfect place to snuggle up with a good book!
Dinner
Start your evening with a delicious, craft cocktail and snacks from Au Comptoir. Bundle up and sit outside around the solo stoves or enjoy their cozy indoor seating.
Make your way to Sante for a delicious dinner of farm to table small bites and entrees. Enjoy locally harvested meats, poultry, fish and produce and a menu that changes with the seasons.
Day Two
Breakfast
You won’t want to miss pancakes or a breakfast burrito at Soulfully Good Cafe! Enjoy a cozy breakfast with hot coffee, a laid-back setting and a classic menu with all your breakfast favorites.
For all coffee connoisseurs, make your way to Abracadabra for a yummy donut and the best coffee in town. Hang out for a fun vibe and good times.
Daytime Exploring
Saskadena Six is one of the first ski areas in North America and Woodstock is proud to be a small mountain community. Saskadena is the perfect mountain to teach your littles to ski for the first time and for those who are more experienced to enjoy some fun and leisurely runs. The lodge is a great place to warm up by the fire, grab lunch and enjoy an apres beverage post-ski.
Strap on your winter hiking boots and layer up for a brisk hike up Mt. Tom or Mt. Peg (weather dependent). Both of these hikes are favorites and provide beautiful views of Woodstock from the peak. Mt. Peg is a shorter hike and more kid-friendly while Mt. Tom is a bit longer, but the trails are wider and jogger friendly. You can’t go wrong either way! If it’s snowy or icy you might want to wear spikes.
Lunch
For a more formal and cozy lunch, make a reservation at Simon Pearce, and dine in a restaurant serving refined American meals in a restored 19th-century mill overlooking a waterfall.
Afternoon Exploring
Spend your afternoon shopping at some of our favorite local businesses. From Farmhouse Pottery to Echo Market and Woody’s Mercantile. Enjoy browsing everything from handmade pottery to fun gifts, artwork, antiques, fun fashion finds and more.
Kid-friendly: If you are in Quechee, pop over to VINS to explore their canopy walk, engage in their diverse programs and see the wild bird rehabilitation.
Dinner
The Prince & The Pauper is a cozy, intimate and romantic spot for dinner on a winter evening. Cozy up at the bar or enjoy a table in the dining room. Choose from their Prix Fixe menu, delicious cocktails and of course desserts!
For a more laid-back vibe, head to Worthy Kitchen for a wide variety of beers on tap, burgers, fries, wings, salads and all your favorite bar grub and vibes.
Winter Weather in Woodstock
Winter weather in Vermont typically ranges from 20-30 degrees, but can also drop into the negatives some days and be a bit warmer other days in the 40s and 50s. Temperatures will typically drop even lower in the evening and on sunny days may even feel “spring-like” during the day. The key to enjoying your time in Woodstock during the winter, is making sure you have plenty of warm layers and being prepared for all the elements and adventures. Be sure to pack a warm insulated winter jacket, hat, mittens and warm insulated water-proof boots. You can layer all your stylish winter outfits underneath your warmer gear.
Winter Packing List for Woodstock, Vermont:
- Pants
- Long sleeves
- Snow boots/sneakers/hiking boots
- Socks/undergarments
- Sweater
- Jacket (warm/heavy coat)
- Snowpants/helmet and ski/snowboard gear
- Warm layers/long-underwear
- Scarf/hat/mittens
- Bag
Getting to Woodstock
Once in Woodstock, the village as a whole is fairly walkable. Car transportation is preferable, convenient and parking is typically easier to find. If you are flying into Boston or Burlington, it will be necessary to rent a car.
Uber/Lyft/taxi’s are not accessible in Woodstock. If you are staying in the village you will be able to walk to and from meals and excursions in town. If you stay at the Woodstock Inn & Resort there are transportation services available. Speak with the concierge to make plans prior to your arrival.
AIRPORTS
The closest airport and most convenient is Lebanon Municipal Airport. It is located about 20 minutes from Woodstock. This is a small airport, flying small planes and flights and connections are limited.
Burlington International is approximately 1.5 hours from Woodstock. This airport is usually less crowded and easier to navigate than Boston.
Boston Logan is approximately 2.5 hours from Woodstock depending on traffic.
BUS
The Dartmouth Coach is a great way to travel if you need transportation from the Boston Airport or another New England City. With destinations to New York City, Boston South Station, Hanover and Lebanon this is an easy and affordable travel option.
TRAIN
The AMTRAK train takes passengers from D.C. and NYC to White River, Vermont about 15 minutes outside of the Woodstock village.
CARS/DRIVING
It is fairly easy to walk most places while in Woodstock, but it does help to have a car if possible, especially for colder months. Vermont is a remote location and things are much more spread out than in cities and suburban towns. Many of our favorite recommendations include a drive out of town from 10-30 minutes. There’s metered parking throughout the village available on most streets. If you get a ticket remember to have a local business validate it for you and you don’t have to pay!
Visiting Woodstock during the winter is the perfect way to get a taste of quintessential New England. Embrace the season and enjoy everything from cozying up by the fireside with a hot toddy to skiing down the slopes at Saskadena Six. You truly can’t go wrong with a getaway to Woodstock, VT during the winter.
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