Woodstock, Vermont Winter Itinerary | Jesse Ann Kirby

Winter in Woodstock is truly magical. Glittery snow, twinkling lights, cozy fireplaces and charming villages. The picturesque village of Woodstock is the perfect winter getaway. Whether you're looking for adventure or want to relax, Woodstock has something for you. Adventure activities range from skiing, hiking and fat biking to more leisurely pursuits like shopping, dining and luxury spa treatments. You can never go wrong. If you’re traveling to Woodstock this winter, look no further. We'll share the best of winter in Woodstock from a local's perspective to ensure you make the most of your time in this charming town.

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Our complete guide to the perfect two-day trip to Woodstock in winter.

Woodstock, Vermont Winter Itinerary

stay

Woodstock Inn & Resort

Woodstock Inn (Book through this link to get 10% off your stay) is one of the most convenient and luxurious places to stay in Woodstock. Staying at the hotel is extra special in the winter, with cozy fireplaces, common areas, restaurants, spa facilities and more. Not to mention it's located in the Village, just minutes from all the downtown shopping and dining you can imagine. Be sure to book spa appointments and meals in advance.

Woodstock Bed and Breakfast

For an intimate and romantic stay, try Woodstock Bed and Breakfast Located outside the village but within easy walking distance of the town centre. This charming B&B features little personal touches and beautiful Vermont-chic rooms to make every stay memorable and unique.

Inn on the River No. 506

Riverside Inn No. 506 It's a great choice for families, with an indoor pool, games room and an on-site restaurant that the whole family can enjoy. Just a short drive outside the village, this is an ideal base for your stay in Woodstock, especially if you have young children.

first day

breakfast

• Enjoy a delicious breakfast Monvet Cafe Located in the center of the village. This is a favorite spot among locals and tourists alike, serving delicious, rustic country fare and espresso. They offer delicious specialty coffee and many comfortable places to dine.
• For a quick snack on the go, breakfast sandwiches, pastries and coffee are available from the restaurant country butcher!

Explore during the day

• Take a brisk stroll through the winter town and get acquainted with the village. Be sure to bundle up and wear comfortable shoes. Walk through the Village Green, the Center Covered Bridge (don't miss the view of the illuminated trailhead from the top of Mount Tom as you approach the bridge), and explore River Road, Mountain Avenue, and Faulkner Park.Take a loop walk through the village and see Some of our favorite shops downtown.
• Stormy Day/Child Friendly Options: Go to woodstock athletic club, part of the Woodstock Inn & Resort facility. If you're not staying at the hotel, you can still purchase a day pass to use the gym, take fitness classes, and enjoy the pool, steam room, sauna, and whirlpool.

Lunch

• For a classic and simple dining experience, head to mountain dairy Just 10 minutes from West Woodstock. Enjoy 1/2 cup soup and specialty salads along with delicious warm sandwich options – perfect for those cold winter days!
• If you want to have lunch on the go, please return country butcher Enjoy one of their delicious fresh sandwiches. Choose from their classics or make your own! You can’t go wrong with fresh meats, breads and produce.

Afternoon exploration

• spend your afternoon nordic center Cross-country skiing, snowshoeing or fat biking. You can rent equipment and even schedule lessons at the Nordic Center. Trails range from beginner to advanced, with something for everyone. After your adventure, enjoy hot or cold drinks, soups and sandwiches at the Fairway Grill, the on-site restaurant!
• Want to stay cozy indoors?Go to Woodstock Hotel and Spa Spend a relaxing afternoon. Choose from a menu of delightful winter seasonal spa treatments and enjoy amenities such as whirlpools, saunas and steam rooms. Not to mention, the cozy lounge and fireplace – the perfect place to snuggle up with a good book!

dinner

• Start your night off with delicious winter craft cocktails and canapés from over the counter. Bundle up and sit outside around the freestanding stove, or enjoy comfortable indoor seating.
• Go to Sant Enjoy a delicious dinner of canapés and entrees. Enjoy locally harvested meat, poultry, fish and produce along with a seasonally changing menu.

the next day

breakfast

• You won’t want to miss the pancakes and waffles here mountain dairy! Enjoy a farm-to-table breakfast with hot coffee, a laid-back setting and a classic menu featuring all your breakfast favorites.
• For all you coffee connoisseurs, go to nonsense Delicious donuts and the best coffee in town. Hang out, enjoy the fun atmosphere and a good time.

Explore during the day

• saskadena six One of the original ski areas in North America, Woodstock is proud to be a small mountain community. Saskadena is the perfect mountain to teach your kids to ski for the first time, and there are some fun and leisurely runs for those who are more experienced. The lodge is a great place to warm up by the fire, have lunch and enjoy a drink after skiing.
• Put on your winter hiking shoes, stack them up, and hike with ease mount tom or mt.nail (depending on weather). Both hikes are popular and offer great views of Woodstock from the top. Mt. Peg's hiking route is shorter and more suitable for children, while Mt. Tom's hiking route is slightly longer, but the trail is wider and more suitable for joggers. You can't go wrong no matter what!If it snows or freezes You may want to wear spikes.

Lunch

• For a delicious lunch within 10 minutes of the city, head to south woodstock store. Order your sandwiches to go or enjoy them in their small, typical seating area. Explore the grocery store and maybe pick up some gifts or souvenirs.
• For a more formal and cozy lunch, Book at Simon Pearceyou can dine in a restaurant serving fine American cuisine, located in a restored 19th-century mill overlooking the falls.

Afternoon exploration

• Afternoon shopping at some of our favorite local stores: Simon Pearce and farmhouse pottery. Enjoy browsing the gorgeous glassware and pottery, and even take a tour of the glassblowing and pottery making crafts.
• Suitable for children: If you're in Quechee, go to wine Explore their canopy walks, participate in their diverse programs, and visit the Wild Bird Rehabilitation Center.

dinner

• The Prince and the Beggar This is a cozy, intimate, romantic place for a winter night dinner. Relax at the bar or enjoy a table in the restaurant. Choose from their Prix Fixe menu, delicious cocktails and desserts!
• For a more laid-back atmosphere, head to Worth the kitchen Huge selection including beers on tap, burgers, fries, wings, salads and all your favorite pub food and atmosphere.

Winter Weather in Woodstock

Winter weather in Vermont is typically between 20 and 30 degrees, but can drop to freezing at times, while other days are in the 40s and 50s. Temperatures often drop even lower at night, and on sunny days it can even feel “spring-like” during the day. The key to enjoying your time at Woodstock in the winter is to make sure you have enough warm clothing and be prepared for all the elements and adventures. Be sure to bring a warm winter coat, hat, gloves and warm waterproof boots.you can Layer all your stylish winter outfits Underneath your thermal gear.

Woodstock, Vermont Winter Packing List:

• Pants
• long sleeves
• Snow boots/sports shoes/hiking boots
• socks/underwear
• sweater
• Jacket (warm/thick coat)
• Snow pants/helmet and ski/snowboard gear
• Thermal layer/long underwear
• Scarf/hat/gloves
• bag

Heading to Woodstock

• Once you get to Woodstock, the entire village is fairly walkable. Car transportation is preferable, convenient, and often easier to find parking.
• If you're flying to Boston or Burlington, you'll need to rent a car.
• Uber/Lyft/Taxi are not available in Woodstock. If you stay in the village, you can walk to and from the town for meals and tours. If you stay at the Woodstock Inn & Resort, you can take advantage of transportation services. Contact the concierge before your arrival to make plans.

Airport

• The closest and most convenient airport is Lebanon Municipal Airport. About 20 minutes from Woodstock. It is a small airport that flies small aircraft and has limited flights and transfers.
• Burlington International is about a 1.5 hour drive from Woodstock. This airport is generally less crowded and easier to navigate than Boston Airport.
• Boston Logan is approximately a 2.5 hour drive from Woodstock, depending on traffic.

the bus

If you need transportation from the Boston Airport or other New England cities, Dartmouth Coach is a great way to travel. With destinations including New York City, Boston South Station, Hanover and Lebanon, this is an easy and affordable travel option.

train

AMTRAK trains carry passengers from Washington, D.C., and New York City to White River, Vermont, about 15 minutes from Woodstock Village.

car/driving

It's fairly easy to get to most places on foot in Woodstock, but having a car does help if possible, especially in the colder months. Vermont is remote and things are more spread out than cities and suburban towns. Many of our favorite suggestions include driving 10 to 30 minutes out of town. Metered parking is available on most streets throughout the village. If you get tickets, remember to ask a local business to verify it for you so you don’t have to pay!

Visiting Woodstock in the winter is the perfect way to experience quintessential New England. Embrace the season and enjoy everything from cozying up by the fireside with a hot toddy to skiing at Saskadina Ski Area Six. You can’t go wrong with a winter vacation in Woodstock, Vermont.