Woodstock, VT Winter Itinerary

How To Wear A Tunic Sweater
By Jess
12 Dec 2023

photography by craig mackay

Click. Read. Love. 12.26.22

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 Lunch 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 perfect 2-day trip to Woodstock during the winter season.

Woodstock, VT Winter Itinerary


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.

The Woodstock B&B

For an intimate and romantic stay, try the Woodstocker B&B located just outside the village, but within easy walking distance of the town center. This charming B&B makes each stay memorable and unique with small personalized touches and beautiful Vermont chic rooms.


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.

Woodstock inn snow - Woodstock Travel Guide
the woodstock inn during winter

Day One


  • 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.


  • For a classic no frills diner experience, head to the Mountain Creamery just 10 minutes out of town in West Woodstock. Enjoy 1/2 cup soup and salad specials and delicious warm sandwich options– perfect for a cold winter day!
  • 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!


  • Start your evening with a delicious, winter 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 small bites and entrees. Enjoy locally harvested meats, poultry, fish and produce and a menu that changes with the seasons.
Woodstock winter activities
Cross country skiing at the Nordic Center in woodstock

Day Two


  • You won’t want to miss pancakes and waffles at the Mountain Creamery! Enjoy a farm-to-table diner 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.


  • For a yummy lunch 10 minutes outside of town, head to The South Woodstock Store. Order sandwiches to-go or enjoy dining in their small, quintessential seating area. Explore the general store and maybe pick up some gifts or souvenirs.
  • 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: Simon Pearce and Farmhouse Pottery. Enjoy browsing the gorgeous glassware and pottery and even getting to see the craft of glassblowing and making pottery.
  • 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 rehab.


  • The Prince & The Pauper is such 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 to beers on tap, burgers, fries, wings, salads and all your favorite bar grub and vibes.
view of saskadena six

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.


  • 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.


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.


The AMTRAK train takes passengers from D.C. and NYC to White River, Vermont about 15 minutes outside of the Woodstock village.


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.

Disclosure: if you buy something through the links on this blog, we may earn an affiliate commission. We only feature products we would personally recommend. Thank you for your support.

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