Winter Vacation in Vermont: 10 Best Vermont Winter Getaways

1. Mad River Valley

• Outdoor Recreation: Sugarbush Resort | Warren Falls | Blueberry Lake Trails
• Stay The Seasons Resort at Sugarbush | Fairytale Cottage
• Eat: Warren Store | Worthy Burger Too | Ben & Jerry Factory for ice-cream
• Must Read: The Best Covered Bridges in Vermont, including Mad River Covered Bridge Loop

I will start this list of best places to visit during your winter vacation in Vermont with the Mad River Valley because if you are short on time, and have only 1-day to explore Vermont, this is seriously the best thing to do.

The drive is so scenic and you will have opportunities to visit some of the towns listed here in this guide, and also, this itinerary offers numerous opportunities to stop along the drive for pictures. Also, to try the taste of Vermont and stop to sample local food, see lots of gorgeous views, and if you love photography as I do, this is a paradise for any outdoor photographer!

This was my top-pick Best Thing to do in Vermont in winter for many reasons.

I choose to take the Covered Bridge Loop, a 42-mile loop that will take you to visit a total of 7 classic New England-covered bridges. But you also have other options for the itinerary, and whatever you choose to explore in the Mad River Valley, you cannot go wrong!

When you choose to explore the Mad River Valley, you will be able to explore the landscape of mountains and hillside farms, as you take in the culture and community of Vermont. You can shop for antiques, sip a craft beer or experience an authentic farm-to-table meal.

If you are looking for more adventure, you can explore the Blueberry Lake Cross-Country Ski Center, and go to the Skatium, an outdoor ice skating rink.

One of the top things to do in this drive is to stop at Ben & Jerry’s factory for a tour and sample their delicious ice cream. This is considered the most popular tourist attraction in Vermont.

Also, plan to stop at the Warren Store to have a grilled cheese sandwich, it is the BEST grilled cheese I ever had in my life! And stop at the stunning Warren Falls, while driving the Mad River Valley, a series of small drops around boulders into deep pools that make excellent swim holes – but not during wintertime, of course.

Below, you will find more details on the Top Places to visit during your winter vacation in Vermont, and one of the places listed on the Mad River Valley – and you can also check the amazing cozy cabins in this area for a romantic gateway.

2. Woodstock is a must-stop during your winter vacation in Vermont

• Outdoor Recreation: Suicide 6 ski Area | Woodstock Center | Mt. Tom & Mt. Peg Trails
• Stay: The Woodstock Inn & Resort | Woodstock Bed and Breakfast
• Eat: The Prince & The Pauper | Simon Pearce Restaurant | Worthy Kitchen
• Must Read: 20 Awesome Things to do in Woodstock, VT

Woodstock should be on top of your list if you are planning a Vermont winter vacation. Woodstock is a small and quaint town with plenty of things to explore in town and the surroundings. Also, this area is where you can find some of the most beautiful covered bridges in Vermont.

Considered one of the most beautiful towns in the United States, here you can find the only National Park in the State of Vermont, the Marsh-Billings-Rockefeller National Historical Park, located in Windsor County near Woodstock.

Take a stroll down Main Street and it is easy to just get lost admiring the stunning old building that turned into a magic place during wintertime and the holiday’s decorations. Here you can also find local artists, craftspeople, and purveyors that capture the Vermont winter wonderland spirit.

For outdoor adventure things to do in Woodstock, you can head to the Nordic skiing and snowshoeing at the Woodstock Nordic Center. If you are looking for skiing or snowboarding, you can head to the Suicide Six Ski Area, located right in Woodstock, or Killington is just a 30-minute drive.

3. Montpelier

• Outdoor Recreation: Stroll around Hubbard Park | Hike to the Camel’s Hump
• Stay: The Inn at Montpelier | Capitol Plaza Hotel by Hilton
• Eat: Kismet Kitchen | Wayside Restaurant Bakery and Creamery. 
• Must Read: 15 Best Cabins to Rent in Vermont

If you have the time and the chance, include Montpelier in your winter Vacation in Vermont itinerary, at least for a half-day visit, and explore the highlights of Vermont’s Capital.

The highlight of Montpelier is visiting the stunning Vermont State House, and right next to the State House there is The Vermont Historical Society Museum which is located inside a gorgeous mansion, where you can learn more about Vermont’s history.

One of my favorite stops during my visit to Montpelier was to visit The Bragg Farm Sugar House. It was amazing to have the opportunity to learn about the famous Vermont maple syrup, and the family that runs this business takes a lot of pride in what they do, by making maple syrup and selling it here for eight generations and counting. The gift shop is amazing, and please, try the maple candy here. I don’t care about sugar, but it is truly AMAZING!

If you are looking for outdoor things to do and if you are lucky to get a sunny day during your winter vacation in Vermont, I recommend going for a walk at the beautiful Hubbard Park, a park covering almost 200 acres and was first opened to the public back in 1899.

And if you are really looking for an outdoor adventure, you can hike the Camel’s Hump, considered one of the top trails to hike in all of Vermont. It’s also one of the highest summits in the state, so it’s not the easiest hike to do.

4. Stowe is the top destination for your winter vacation in Vermont

• Outdoor Recreation: Stowe Mountain Resort | Trappy Family Lodge Outdoor Center | Stowe Recreation path | Cady Hill Forest
• Stay: Trapp Family Lodge | Green Mountain Inn | Green Mountain Inn
• Eat: Trapp Family Lodge | Idletyme Brewing Co. | Tres Amigos | Cork Restaurant
• Must Read: 13 Awesome Things to do in Stowe

A winter vacation in Vermont must include a visit to Stowe. Located in a beautiful region at the foot of Vermont’s highest peak Mount Mansfield, Stowe has so many amazing things to do, and it is well-known for being a perfect four-season destination. But during wintertime is when the magic happens.

With more than 60 unique shops for shopping, or at least for visiting – and with 40 restaurants there are plenty of things to do in Stowe for everyone. Stowe is also a world-class outdoor recreation paired with historical and cultural experiences, making Stowe a very distinctive New England destination.

A must-do while in Stowe is to have a local beer or lunch at the Trapp Family Lodge, they have Austrian cuisine and the food is phenomenal here. Must try the chicken schnitzel or the grilled bratwurst sandwich…it is to die for!

But keep in mind that they are very busy, and it is recommended to make reservations in advance. And if you are looking for adventure, the Trapp Family Lodge is also very conveniently situated on the cross-country ski and mountain bike trails.

Looking for outdoor adventures? Stowe is for you! The area surrounding it is the reason Vermont is known as America’s Winter Playground. A paradise for skiing, you can also try fat biking, snowmobiling, and dog sledding. And if you are seeking more adventure during your Vermont winter getaway, you can book a half or full-day ice climbing with Sunrise Mountain Guides. 

5. Burlington

• Outdoor Recreation: Lake Champlain
• Stay: Williston Village Inn | Essex Resort
• Eat: Hen of Wood | The Farmhouse Tap & Grill | American Flatbread
• Must Read: 15 Fun Things to do in Burlington

Burlington was my favorite city to visit during my winter vacation in Vermont, with beautiful views located along the Lake Champlain and amazing restaurants to choose from, I didn’t have one single average meal in Burlington. They all offer very high-quality food!

With a population of a little over 43,000 people living in this charming city, Burlington is away from the hustle and bustle of a big city, and I love the laid-back spirit here.

One of the best things to do in Burlington during the winter months is to stroll around the Church Street Marketplace. It is beautifully decorated with twinkling Christmas lights at this time of the year, and a pedestrian road lined with unique shops, restaurants, and cafes.

You can pop in and out of the shops, and catch some street performers.

I recommend stopping at the Archives Bar during your trip to Burlington and trying some of the exotic and unique drinks, while you can enjoy the vintage arcade including video games such as Pac-Man, The Simpsons, Mortal Combat, and several different pinball games.

If you are looking for outdoor activities to do in Burlington in winter, you can stroll along Lake Champlain for beautiful views of the lake. Sometimes the lake freezes in winter and (with caution) you can walk down the lake. If you are looking to go skiing, you have the option to take day trips from Burlington, just don’t forget to check the Snow Conditions in Vermont, and pick the best option for you.

6. Shelburne

• Outdoor Recreation: Shelburne Farms for views of forest and hiking trails
• Stay: Quality Inn Shelburn
• Eat: Barkeaters | The Bearded Frog | Rustic Roots
• Must Read: Perfect Vermont Road Trip Itinerary

Shelburn is a small, but this very charming town that truly captures the essence of Vermont. It is a great alternative for a day trip from Burlington, within a very short driving distance.

You can make a stop at the Shelburne Museum. This is one of the best museums in the entire state and it’s nestled on 45 acres with spectacular scenic views. It holds one of the world’s largest collections of American folk art, with artifacts telling the story of Vermont and buildings transported to the museum for preservation.

Stop at the Shelburn Country Store, an original 1859 Vermont Country Store where you can find local gifts candies, Christmas decorations, and even clothes. The store seems small from the outside, but it has 7 rooms filled with all Vermont things, and even better – it is not a tourist trap, with reasonable prices.

One of the highlights of your visit is visit the Shelburne Farms with miles of walking trails with scenic views of the farms and the surrounding forests, fields, mountains, and of course, the Lake Champlain. This all while you get to visit a working farm with an educational center for sustainability, try some fresh cheese, visit the organic bakery – You got to try the fresh buttery croissant!

7. Middlebury

• Outdoor Recreation:  Green and the Adirondack Mountains for hiking nearby lakes and streams
• Stay: Swift House Inn | Courtyard by Marriott
• Eat: Fire & Ice Restaurant | Otter Creek Brewing Company | The rooms at the Stone Mill

This is another small, but this very quaint town in Vermont that deserves a day’s visit during your winter vacation in Vermont. It is also a very short drive from Burlington, making it a good day trip to visit Sherburn and Middlebury on the same day.

Middlebury could be one of the small towns in Europe – at least this is how I felt during my visit – with brick and stone buildings and the gently sloping town green and cascading falls of Otter Creek. You will love to just stroll around Main Street and see the old buildings, including the white-steepled church, visit the unique local shops, and visit the Middlebury College Bread Loaf Campus. 

If you are looking for outdoor things to do, you can find hiking trails, fly fishing, bird watching, alpine, and cross-country skiing. The Middlebury College Bowl and several nearby Nordic and snowshoe centers offer great winter fun. The Green Mountain National Forest offers challenging terrain and access to Vermont’s Long Trail. The area is also known for excellent bicycling in the rolling farmlands and foothills of the Green Mountains.

8. Brattleboro

• Outdoor Recreation: Green Mountain National Forest for the 9 miles of retreat trails | Fort Dummer State Park | Harris Hill Ski Jump 
• Stay: Inn on Putney Road | Travel by Wyndham
• Eat: Top of the Hill | Whetstone Station Restaurant and Brewery | T.J. Buckley’s
• Must Read: 15 Best Inns & Boutique Hotels in Vermont

Brattleboro was my first stop during my winter vacation in Vermont, and it was a great introduction to the best gateways I planned to visit. Brattleboro is located in Southern Vermont on the bank of the Connecticut River, and it is a popular place to visit because of the excellent skiing, snowshoeing, and skating in the winter.

One of the highlights is to visit the Creamery Covered Bridge, also known as the West Hill Covered Bridge, built-in 1879, it was named after a creamery that was located adjacent to the bridge.

Another must-stop place in Brattleboro is the Grafton Village Cheese Co. If you love cheese, you will love this place, since they have a wide selection of cheeses and they are ALL AMAZING! If you don’t love cheese, don’t worry, they still have a large collection of Vermont Syrup and other local products. They are a Cooperative Cheese company operating since 1892.

Just next door, you can visit the historic Retreat Farm, being an authentic reflection of the rural lifestyle in Vermont. You can also pet and feed the farm animals, or go on some of the 5 trailheads that make up the 9-mile Retreat Trails recreation network, which is open year-round for hikers, bikers, horseback riders, and skiers.

9. Waitsfield

• Outdoor Recreation: Mad River Glen & Sugarbush | Sugarbush Resort
• Stay: 1824 House Inn + Barn | Mad River Lodge
• Eat: Worthy Burger Too | The American Flat Bread Co. | Three Mountain Cafe

Waitsfield was the place I chose to stay during my winter vacation in Vermont. I rented a cabin in the area and had the best time just relaxing, exploring the Mad River Valley and the stunning snow-covered surrounding areas. While I was here, I was recommended a couple of the places the locals love to go – and now I love them too and I can recommend them to you.

If you are into local beer, there are several breweries to visit such as the Lawsons Brewery and Worthy Burger Too which is a must-go! John and Sean run the bar and are always fun to hang with for a burger and many fun local beers.

There’s Three Mountain Cafe in Waitsfield also. It’s open until noon and a great place for pastries with terrific coffee drinks. There are puzzles out that you can help put together while you hang out.

Stroll around the village, and admire the Christmas decor and string lights looped across the eaves and the B&B. Visit the local shops on Bridge Street for clothing, painting, jewelry, and sculpture by local artists.

if you are looking for outdoor adventures, you can stop at Clearwater Sports to rent any equipment you may need from snowshoes to ski and even alpine touring equipment. Plan on spending the day at Sugarbush Resort or Mad River Glen, two ski areas within a 10-minute drive from the center of town, and check out the Mad River Valley’s plethora of other recreational opportunities.

10. Waterbury is a great winter vacation in Vermont

• Outdoor Recreation: Green Mountain Byway 
• Stay: Fairfield by Marriott | Gruberg Haus Inn & Cabins | Old Stagecoach Inn
• Eat: Ben & Jerry for ice cream | Arvad’s Grill | Prohibition Pig
• Must Read: 15 Best Cabins to Rent in Vermont

Waterbury is a perfect stop during your winter vacation in Vermont, especially if you are looking to taste the great food and local beer. With several acclaimed restaurants offering amazing fresh meals in farm-to-table style, and many craft beers to try.

Waterbury is also home to amazing cheese, donuts, and chocolate. Plus, it is home to Ben & Jerry, considered today one of Vermont’s most popular tourist attractions.

But you can find more than food in Waterbury – you can visit many local boutiques and superb small businesses where you can find everything from art to artisanal beverages, books to bikes, and crafts to clothing. Stroll around Waterbury’s recently transformed downtown or take a drive up scenic Route 100.

Here you can also get outside and explore the outdoor adventures around Waterbury, such as riding your bike at the award-winning trails network. During winter in Waterbury, it becomes a winter wonderland of snow sports, with skiing, snowboarding, fat tire biking, snowmobiling, and all between – here you can find many ways to explore your winter vacation in Vermont, including renting a cozy cabin for a more authentic experience.

You need to plan the right packing for your winter vacation in Vermont. Make sure you are prepared, considering the season and the activities you are planning to do. Here are some quick tips:

• Pack layers are the best you can do!
• Pack rain gear – you don’t want to get soaked wet while exploring
• A hat, gloves, and scarf can’t go wrong, even in summer.
• Bring good quality sturdy snow boots.
• Bring warm leggings to wear as a layer is a smart choice!
• Pack a good and warm jacket a waterproof jacket for your trip, check my complete review guide on the Top Jackets for Travel
• If you are planning to carry a backpack for your trip to Vermont, I have compiled a very detailed review of the Best Backpacks for Travel on the market today

If you are planning your winter vacation in Vermont, you will find lots of things to do – and it is a perfect destination for couples, families, or outdoor enthusiasts.

Nowhere does winter like Vermont, whether you ski or ride, there’s no shortage of ways to seize the season – think snowshoeing, snowmobiling, ice fishing, or a winter hike. But Vermont is not only big in outdoor adventures.

Plan to have plenty of fresh farm-to-table meals, explore the local breweries, and simply enjoy some quiet time by driving in the rural and small towns in Vermont. You will love it all!

If you have any additional questions, just leave me a comment below.