Things to do in Southern Vermont in Winter

Megan and Scott enjoying their Southern Vermont winter vacation in an a frame cabin in dover vermont

Looking for all the amazing things to do in Southern Vermont in winter to help you plan your ultimate cold-weather getaway? We’ve got you covered. Southern Vermont offers an incredible array of activities to enjoy all year long, but there’s something extra special about this region in the winter months that makes it the perfect getaway on the East Coast.

The abundance of snow that this region gets makes it ideal for all kinds of fun Southern Vermont attractions in the winter from hitting the slopes at the many ski resorts in the area, outdoor activities from ice skating to snowmobiling, staying in a cozy lodge or cabin, and of course, exploring the charming towns and roadside stops from cute shops to those charming covered bridges you can find scattered all throughout New England.

So if you need a little inspiration or help planning your Southern Vermont winter vacation, this guide has you covered including great ideas for things to do in Southern Vermont in winter, where to visit, and where to stay!

Disclaimer: This post contains affiliate links.

Southern Vermont Winter Vacation Guide

Hit the Slopes

skiing at Mount Snow in Dover Vermont

One of the most popular things to do in Southern Vermont during the winter is hitting the slopes! Whether you want to ski, snowboard, or just admire the view from the ski lift (although you’ll need to get down the mountain somehow), there are many great Southern Vermont attractions to choose from.

Below are some of the best mountains and ski resorts to hit the slopes in this area! 

Mount Snow

Mount Snow in winter in Dover Vermont

Mount Snow is a popular mountain and ski resort in Southern Vermont. Located in the Green Mountains with the nearest towns being Dover and West Dover, this popular skiing spot has been operating as a ski resort since 1954! In fact, it was one of the first ski resorts to open on the East Coast! 

With over a dozen places to eat, multiple spas in the area, and three shops to buy snow gear, Mount Snow has everything you’ll need during a busy day on the slopes.

In addition, Mount Snow has many trails to choose from and is great for a wide range of skiers and snowboarders. So whether you’re a beginner or expert, you’ll be able to find a good place on Mount Snow! You’ll also be able to enjoy the incredible views from the top of the mountain and the ski lift. 

Since Mount Snow is such a popular Southern Vermont winter attraction, you can expect that the busiest time will be on the weekends. However, the lines typically move very quickly during the week! 

There are many places to stay on Mount Snow if you’re looking for more of a resort-style stay, otherwise, we mention a few great other options like the cabin we stayed at further on in this guide.

Carinthia Base Lodge is a great place to stay that has a public restaurant, outdoor fire pit, heated pool, sauna, and steam room!

Another great option is Grand Summit Resort Hotel. This is an excellent place for anyone who wants to spend time at the spa! 

Stratton Mountain 

Base of Stratton Mountain skiing and snowboarding options in Southern Vermont

Stratton Mountain is a ski resort and mountain with over 90 trails! Known as one of the most popular Southern Vermont attractions, Stratton Mountain ski resort is located in a small, cozy snow village with many shops and restaurants.

Although this destination is typically less crowded than Mount Snow, you can expect the lines to get slightly longer during the holiday season. 

Stratton Mountain is great for skiers and snowboarders of all levels since the mountain has many trails to choose from and isn’t as tall as the others nearby. If you visit this popular mountain, you can get skiing and snowboarding lessons, a guided tour of the village, access to an ice skating rink, and many other activities! 

Bromley Mountain

If you want a serene, Southern Vermont winter vacation, Bromely Mountain in Peru, Vermont is a perfect option. Located in the Green Mountains, Bromley Mountain is a popular skiing and snowboarding destination that is a great spot if you want to avoid the level of tourism of the nearby popular mountains.

Bromley Mountain is known for its variety of terrains and alpine slides. People also love to camp in this area!

Keep in mind that Peru is a small, calm town that’s great for families looking for a serene winter vacation in Vermont. This is a destination you may want to book a cabin and relax a bit.

Visit Stratton Village 

Stratton Village at the ski resort at Stratton Mountain in Vermont

So we’ve covered where to go skiing or snowboarding including Stratton Mountain. But now we are going to focus on the village at this popular Southern Vermont winter mountain resort.

Stratton Village is a great place to shop and dine next to Stratton Mountain! This charming, alpine village has many great family-friendly restaurants, markets, and shops.

The best dining options here include Fire Tower for an excellent apres experience, Mulligans for a classic meal, and Mad Coffee Roasters for delicious coffee and baked goods. There are also many places to get craft beers and spirits!

Immerse yourself in Southern Vermont in winter even more by going shopping and getting a souvenir to remember your trip! At Stratton Village, there are many places to get snow gear and shop winter apparel at any of the branded sports shops from Burton to The North Face. 

In addition, you can find a market for local grocery items as well as a few gift shops selling branded and locally inspired souvenirs to remember your Southern Vermont winter vacation by!

Ice Skating 

ice skating at Farm Road Estate near Mount Snow in Dover Vermont

A Southern Vermont winter vacation wouldn’t be complete without ice skating! Farm Road Estate, just minutes away from Mount Snow, is a great place to stay, dine, and ice skate!

Admission to this outdoor ice skating rink is only $5, and it is only another $5 to rent skates. In addition, they serve hot cocoa and other drinks all day long next to the rink!

Another great place to go ice skating is at Stratton Mountain’s ice skating rink! This rink is located at The Mill House and is $15 for ice skating and $45 for ice skating lessons. So if you want a rink that has excellent music and cozy fires nearby, this is the perfect pick for you!

Snow Tubing 

snow tube race at Leland Snowplay

Snow tubing is one of the most popular things to do in Southern Vermont in winter! One of the best places to go tubing is at Mount Snow. With up to eight lanes to choose from, Mount Snow has one of the biggest snow tubing hills in the entire state.

Located at the base of the mountain, this snow tubing area is known as “the magic carpet” and is an excellent activity for people of all ages. 

Another great place to go snow tubing is at the Coca-Cola Tube Park on Stratton Mountain! Here, you can find lift-serviced snow tubing with drinks and fire pits nearby. Located in the area known as the Sun Bowl, this spot has four high-speed lanes that are great for anyone five years and older who want to go snow tubing! 

Snowshoe

snowshoeing in Montreal Quebec on Mont Royal

One of the best ways to enjoy Southern Vermont in winter is to snowshoe! If you have your own snowshoes, you can hit up many trails on Mount Snow and in the Green Mountains.

One popular trail in the Green Mountains is the Bucklin Trail. If you go up to Killington Peak, you can get a great view of the mountains! This trail is just over 7 miles and is great if you want to spend a few hours outdoors that day. 

Another great trail in the Green Mountains is the White Rocks Recreation Area Trail. This trail is about 4 miles long and is on the Long Trail!

If you’re looking for a more leisurely day outside with less elevation, The Robert Frost Interpretive Trail is a great pick. This trail is in the Green Mountain National Forest, is less than a mile long, and is great for immersing yourself in nature!

If you need to rent snowshoes, Timber Creek is a great place to get them as well as ideas for where to go for the day if you’re unsure. Around here, there are many great trails that will immerse you in the woods!

Other Outdoor Activities

Megan and Scott laughing and falling snowshoeing in Monts Valin National Park in winter in Saguenay lac saint jean quebec

Fat Bike Tires 

No Southern Vermont winter vacation is complete without a fat bike ride! Fat bikes are bikes with fat tires meant to be ridden in the snow and can also be used in the sand. Going on a fat bike ride is similar to mountain biking in the snow!

Many resorts in Southern Vermont offer fat bike rides, including The Nordic Center on Stratton Mountain. 

Cross Country Skiing

Cross country skiing allows you to go up, down, and across various terrains without a ski lift or other assistance. One of the most popular places to go cross country skiing in Southern Vermont is Timber Creek! Right across from Mount Snow, Timber Creek has a massive trail system and many hills that will take you through the forest. 

Snowmobile Tours

One of the best things to do in Southern Vermont in the winter is to take a snowmobile tour! Mount Snow offers snowmobile tours that start at two hours in length. This snowmobile tour takes you through the Green Mountain National Forest and the Vermont State trail system! 

Another great place to take a snowmobile tour is Stratton Mountain! Great for beginners and experienced snowmobilers, the tours on Stratton Mountain can be with a guide, and you can choose where to start the tour! You can also do mini 10-25 minute rides if you’re looking for something quicker and more affordable. 

Winter Hiking

One of the best ways to explore Southern Vermont in winter is to go on a winter hike! Stratton Mountain is a great place to hike in Southern Vermont. Stratton Mountain is Southern Vermont’s tallest peak, with the top of the mountain rising to almost 3,500 feet!

If you choose to go to the top of the mountain from the base, it will be a 6-mile round trip hike. Keep an eye out for the incredible views at the top!

Another great place to go on a winter hike is Lake Shaftsbury Park. Located in Shaftsbury, this 84-acre park has a one-mile trail that loops around the lake. This is a great hiking spot for families and is also known as a great picnic spot!

If you don’t have your own snowshoes or gear, get these great boot grips for snow and ice before your trip. These are great for traveling light and also perfect to just throw on your snow boots when you want to go on a hike or walk with an extra grip in the snow or ice.

Horse Drawn Winter Sleigh Ride

As someone who grew up with Belgian horses on my family farm, this one felt like some childhood nostalgia and a reminder of my Great Grandpa who would bring the horses out with their sleighs to get through the mud during maple syrup season. So when we discovered that Southern Vermont offered winter horse-drawn sleigh rides we were pretty intrigued!

One of the best places to take a horse-drawn winter sleigh ride is Friesians of Majesty. Located in the center of many Southern Vermont ski resorts, the Friesians of Majesty sleigh rides will take you through various parts of the forest and snow meadows! This stunning farm is surrounded by many mountains and lots of animal life!

Another great place that offers sleigh rides is Taylor Farm. These 45-minute sleigh rides can hold up to 12 adults and include a stop to enjoy hot cider and roast marshmallows by the fire!

Each sleigh comes with a wool blanket, and there are options to book a private ride for a romantic experience or for your family as well as group rides.

Visit Charming Towns

Dots restaurant in Wilmington Vermont

Wilmington 

Wilmington is a charming town in Vermont known for its unique shops, historic buildings, and many art galleries. If you’re into art galleries, be sure to check out one of their most popular: The Art of Humor Gallery!

Another great thing to do here is dine at one of the many unique restaurants. Dot’s is a classic American restaurant with a retro vibe that’s worth checking out at any time of the day! 

Wilmington also has many great beaches for having a picnic or admiring the many mountains. Boyd Hill Road Picnic Area and Woods Road Picnic Area are two scenic spots worth checking out. Don’t miss our complete guide for things to do in Wilmington for more ideas!

Bennington 

Bennington is a charming town in Delaware known for being the home of the Bennington Battle Monument, the largest human-made structure in the entire state! This charming town also has many museums, including the Bennington Museum, great for any art and history lover.

If you want to take a scenic drive, be sure to drive by Molly Stark Trail. If you’re more of a walker, be sure to walk underneath the Silk Road Covered Bridge that’s nearby as well!

Brattleboro 

Another charming town worth visiting is Brattleboro. This small town is home to the New England Center for Circus Arts and the Vermont Jazz Center in Windham County! 

Brattleboro also has an extensive network of trails just south of the Green Mountain National Forest. If you want to go hiking, this is a great spot!

There are also many great places to dine in Brattleboro. One of the most popular places to eat and grab a drink is Whetstone Station Restaurant and Brewery, which has a lovely patio with a great view!

Stop at Charming New England Shops

Stratton Parsonage store in Stratton Vermont in winter

The Stratton Parsonage 

The Stratton Parsonage is a popular gift shop in Stratton, Vermont. This little shop is only a few minutes from Stratton Mountain and is known for its delicious, homemade maple syrup! You can also find other items like handmade soap and unique gifts.

Worn New England 

Worn New England is a collectibles store in Dover, Vermont. Here, you can find handcrafted country furniture and other items for your home!

Grafton Village Cheese 

Grafton Village Cheese is a cheese shop in Brattleboro, Vermont. On top of its delicious cheeses, this shop also sells jams, locally sourced wine, chocolates, and other goodies! This cheese shop is located on a beautiful farm filled with animals to pet and feed. There is also a stream nearby with picnic tables! 

Vermont Antique Mall 

The Vermont Antique Mall is an antique mall with over 130 unique vendors! Located in Quechee Gorge Village, this mall is a great place to find one-of-a-kind antique and handmade goods. So whether you want a delicious bottle of wine and cheese or toys for your kids, you’ll be able to find them here.

Hit Up the Breweries

megan having a craft beer

One of the most popular Southern Vermont attractions is the excellent breweries! Something we discovered was that when we were experimenting trying craft brews at home, anytime we tried a Vermont beer we LOVED it. So we were naturally pretty excited to be able to sample more of the brews from the region and they did not disappoint. I don’t think either of us tried a beer or cider from Vermont we didn’t love.

If you want to add a brewery to your Southern Vermont winter vacation itinerary, check out a few mentioned below.

Snow Republic

Voted the best brewery in West Dover, Snow Republic is a brewery and taproom three miles away from Mount Snow. This brewery has a lovely patio and sometimes has live music outside!

Beer Naked Brewery

Beer Naked Brewery is a mountain top brewery in Marlboro, Vermont. This brewery serves a wide variety of ales and beers and is excellent for anyone who wants a great view!

The Tap House at Catamount Glass 

The Tap House at Catamount Glass is a taphouse and pub in Bennington, Vermont. Although this place is technically a tap house and not a brewery, it is mainly known for its 16 different beers!

Madison’s Brewing Company 

Madison’s Brewing Company is another brewery in Bennington, Vermont. This brewery and pub-style restaurant has award-winning beer and great food!

Take a scenic drive to Covered Bridges

a kiss under Island Properties Covered Bridge in Peru Vermont

One of the most popular Southern Vermont attractions is the covered bridges! Vermont has the most covered bridges per square male in America. In fact, there are over 100 covered bridges in the state!

We are big fans of covered bridges in New York, so naturally, we had fun trying to visit as many as we could on our Southern Vermont winter vacation.

Paper Mill Village Bridge 

Paper Mill Village Bridge is a covered bridge in Bennington that was built in 1889. This bridge carries Murphy Road across the Waloomsac River. If you want to stop and get closer to see the river, rest assured that there is parking on the north side of the bridge. This bridge is also very close to Silk Bridge and Henry Bridge! 

Kidder Hill Bridge 

Built in 1870, Kidder Hill Bridge is a covered bridge on the South edge of Grafton. This 67-foot long bridge carries Kidder Hill Road over the Saxton River.

Chiselville Bridge 

Chiselville Bridge is a covered bridge in Sunderland, Vermont. Built in 1870, the Chiselville Bridge is right over the Roaring Branch Brook. Many visitors like to go to the bottom of the ravine to see the bridge from below! If this interests you, keep in mind that there is parking nearby on the north side of the bridge.

Hermitage Road Covered Bridge 

The Hermitage Road Covered Bridge is a covered bridge that leads to the Hermitage Inn in West Dover, Vermont. Unlike many of the other old, historic-covered bridges nearby, this bridge is relatively new and was built in 2009!

Although it isn’t an old bridge, it has a unique vintage feel. This bridge crosses above a mountain stream called Cold Brook and is one of Vermont’s most photogenic landmarks right by Mount Snow.

Island Properties Covered Bridge

Island Properties Covered Bridge is a large covered bridge in Jamaica, Vermont. If you want to immerse yourself in nature and get a feel for the winter scenery, this is the perfect bridge to visit! This one is easy to miss, be sure to look as it’s located downhill and leads to homes. It’s fine to visit the bridge here, but don’t go exploring beyond the bridge as these are residences.

Scott Covered Bridge

The Scott Covered Bridge in Townshend, Vermont is one of the longest covered bridges in the state. Spanning 277 feet long, this large bridge goes over the West River. Visitors can stop at either side of the bridge to take photos and go inside to read more about the landmark’s history! 

Try New England Candlepin Bowling

One of the best things to do in Southern Vermont is to try candlepin bowling! New England candlepin bowling is a sport that is almost totally exclusive to New England!

Invented in 1880, this sport has remained a popular activity in the area. Instead of large bowling balls, candlepin bowling involves small balls held in one hand. These can then be thrown at the palindromic pins. These pins are the same upside down as they are right-side-up, making them easier to fall over. 

North Star Bowling is a popular bowling alley in Wilmington, Vermont. This spot has candlepin bowling, an arcade, mini-golf, and lots of food! 

Cozy up in a Cabin

reading a book in our cozy a frame cabin in dover vermont

One of the best things to do in Southern Vermont in the winter is cozy up in a gorgeous cabin during your getaway! There’s something so beautiful about the wintery landscape of New England and the dreamy cabin rentals available!

We stayed at this gorgeous A-Frame Alpine Cabin in West Dover which was the perfect base for a Southern Vermont winter vacation as the house can sleep up 7 people equipped with 5 beds, a full kitchen, 2 bathrooms, a cozy fireplace, and of course an outdoor hot tub surrounded by the forest.

The main bedroom and outdoor deck where the hot tub is located offers views of Mount Snow and is only a 5-minute drive from the ski resort which makes it a prime location in Southern Vermont in winter not to mention Stratton Mountain is only a 20-minute drive away too!

This dreamy A-Frame cabin is what winter vacation goals are made of. Better yet, you can rent out the place for a spacious romantic couples getaway like we did, a family-friendly getaway, or a friend’s trip! Book here on Vrbo.

Where to Stay in Southern Vermont

Mount Snow Grand Resort in Dover Vermont

As already mentioned, you can’t go wrong with booking a dreamy little cabin during your Southern Vermont winter vacation! In addition to some cool individual properties like the one we mentioned above, each of the ski resorts has their own accommodation which makes for the perfect base while exploring the Southern Vermont attractions while being right next to the mountain to hit the slopes and other outdoor activities in the area!

Here are a few of the best resorts you can stay at during your Southern Vermont winter vacation and getaway.

Mount Snow Grand Resort

This ski-in ski-out mountain resort located at Mount Snow in Dover is the perfect base for your snow play on your Southern Vermont winter vacation! This resort also has a restaurant and bar on-site and a full-service spa for that much-needed relaxation after a long day on the slopes.

There is free parking on-site and you are less than a minute walk to the base of the mountain. Book here.

Black Bear Lodge in Stratton

Another great option for where to base during your getaway enjoying all the best things to do in Southern Vermont in winter is at Black Bear Lodge in Stratton. This ski lodge is a quick walk to Stratton Village and offers a winter shuttle to the mountain for those who want to hit the slopes.

They have an on-site restaurant and bar, complimentary continental breakfast, and an indoor hot tub and sauna for guests to soak in on those extra chilly days! This is one of the few resorts in the area that also has a pet-friendly policy too! Book here.

The Lodge at Bromley

Another great option for where to stay during your Southern Vermont winter vacation is at Bromley Ski Resort in Peru, Vermont. The Lodge at Bromley is located at Bromley Mountain in a retro 1970s style Swiss chalet that offers ski-in and ski-out rooms for those wanting to partake in Southern Vermont winter activities on the slopes!

This casual lodge is perfect for families and compared to the other ski resorts in the area this one is a bit more budget-friendly. Book here.

What to Pack for Your Southern Vermont Winter Getaway

Scott grabbing firewood at our Vermont cabin getaway in Dover VT in winter

You will want to come prepared with the proper packing essentials to ensure that you’re comfortable so you can enjoy all the beauty and best things to do in Southern Vermont in winter.

Let’s start with your attire, the key is to layer. You will want to make sure you have a warm winter jacket, we recommend bringing one that can handle wetter, snowy conditions so that your jacket keeps you dry. I have this North Face winter parka (they have a Men’s winter parka too) that kept me warm and dry. 

We also recommend having layering thermals for the really cold days. I have a thin, long-sleeved thermal I like to wear under my sweaters and Scott wore a long-sleeved thermal under his flannels that helped regulate his temperature. We like the Uniqlo brand of Heattech thermals because they include insulation without overheating or being bulky (plus use fabrics that are moisture-wicking, anti-static, and have odor control).

It goes without saying, make sure you also have a scarf, winter hat, gloves or mittens, and thick, warm socks. We really like the thick, warm socks from Roots. If you’re in snowy conditions you may want to pack extra socks. Sometimes snow sneaks in the top of your boots and it’s nice to have a fresh pair to change into halfway throughout the day or before going out for the evening.

One of the most important parts of your body to keep warm and dry are your feet! This is why we highly recommend having a quality pair of snow boots, because if you’re visiting Southern Vermont in winter, you’re going to be walking in snow!

We both are huge fans of Sorel boots, Scott has the Men’s Caribou Boot and I have a pair of their women’s snow boots as well which are great at keeping your feet dry and warm even on the wettest and coldest of winter days.

We love to pack some hand warmers. There are disposable, single-use ones that can come in handy (in the winter we always have a spare pack of these in Scott’s camera backpack and my purse). They even have toe warmers too in case your toes get extra chilly.

The holy grail of hand warmers though are rechargeable hand warmers. We LOVE ours and they last all day – just remember to charge again at night. I like to have it on the low setting in my winter jacket pocket to keep my phone warm too (since phone batteries hate the cold weather). We tried a few brands and not all rechargeable hand warmers are created equal – this is the one we have and it’s the best.

One thing I wish we had were ice grips for our snow boots. These are not only affordable and take up no space in your luggage, but they are also really great for walking on icy sidewalks and packed down snow, even with snow boots. 

What’s great is that if you don’t have snowboarding or skiing clothing or gear you can easily rent them at multiple shops around the resort at which you’ll be skiing/snowboarding at! 


Found this guide to all the best things to do in Southern Vermont in winter helpful? Bookmark for later and use this to plan your next trip!

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