The Ultimate Vermont Winter Itinerary: 7 Days in Vermont

Don’t escape winter, embrace it. Vermont is the perfect place to do exactly that. Vermont in the winter is the inside of a snow globe come to life. I quickly fell in love with Vermont in wintertime for its amazing outdoor adventures, adorable small towns, and stunning snowy scenery everywhere I looked.

Pack up the car, gather your travel buddies and take a road trip to Vermont in the winter. This travel guide is ideal for anyone looking to plan a trip to Vermont in December, January, February or March…and you don’t know where to start. I hope you can find some valuable inspiration in my Vermont winter itinerary for 7 brilliant days in the Green Mountains and beyond.

In this Vermont winter itinerary, I’m going to show you how to spend a wonderful week in Vermont. We’ll be staying at three unique accommodations for this trip, each with their own great things to see and do. I’ll outline where to stay, what to do, and where to dine.

While learning how to ski as a true beginner, both downhill and cross-country, seemed a little bit daunting at first, I quickly picked up these new skills during my ski lessons with qualified instructors. I went from a non-skier to someone who can’t stop thinking about the next time I’ll be able to ski.

With that said, you don’t have to ski to enjoy this travel itinerary. I’ll share a wide variety of activities whether you love to ski or you’d rather be curled up at the fireplace with a good book. Let’s not forget that Vermont has some of the best après-ski, too!

Vermont Winter Itinerary: Stowe (Days 1 & 2)

It’s day one in Vermont and I’m starting off this Vermont winter itinerary in the town of Stowe. We drove to Vermont from Toronto, which takes around eight hours in total. Your drive might be shorter or longer than this, so you may have more time to spend in Stowe.

We’ll start our day by arriving at the Trapp Family Lodge and settling in for the evening. Enjoy a delicious meal and a pint at the Von Trapp Brewing Bierhaus, and make yourself at home at the Trapp Family Lodge. This property encourages its guests to make use of the many public spaces, like libraries and game rooms.

I experienced the majority of the activities listed here on the second day of my trip. If you find yourself with some more time on day one, I recommend going snowshoeing or cross-country skiing through the Trapp Family Lodge’s activity center.

Stay at the Trapp Family Lodge (2 Nights)

Am I still in Vermont or did I somehow transport myself to Austria? The Trapp Family Lodge brings a slice of Austria to the eastern USA through its architecture, history, stories and food. With the classic Austrian-style buildings and the mountains looming in the distance, you will truly feel like you’re in Europe.

If the Von Trapp name sounds familiar to you, it’s because this is the real von Trapp family that inspired one of the most famous films of all time, The Sound of Music. The entire property is family owned and operated by the von Trapp family, including Sam von Trapp and Kristina von Trapp Frame, the grandchildren of Maria and Captain von Trapp.

My room at the Trapp Family Lodge was spacious, yet cozy, with its own balcony that was perfect for watching the sunrise. The property itself features several common areas, like libraries, board game rooms, and other places to gather with family and friends. Many of these spaces have their own fireplaces, which adds to the snug atmosphere. Book your stay at the Trapp Family Lodge.

Von Trapp Brewing

The Austrian inspiration surrounding the Trapp Family Lodge extends to their brewery, Von Trapp Brewing. It is possible to take a beer tour at Von Trapp Brewing on specified dates and times, though I recommend stopping by their Bierhall anytime to enjoy a meal and a pint.

Pair a fresh brew with an Austrian-inspired dish, like pretzels, brats, sauerkraut or cheddar lager soup. I was really pleased with my black bean and farro burger with locally sourced mushrooms and housemade pickles.

The beer is also exceptional. As I prefer lighter beers, I opted for the Helles golden lager. Next time, I wouldn’t mind trying their Smoked Helles, which would transport me right back to Bamberg, Germany!

Trapp Family Lodge History Tour

If you’re a fan of The Sound of Music or simply want to know more about the property and the family behind it, I encourage you to sign up for the Trapp Family Lodge History Tour. When you arrive at the Trapp Family Lodge, you’ll receive information about the guest activities and tours happening throughout the week.

On select days of the week, join a 90 minute tour with an overview of the von Trapp family history. A historian will tour you through the property, discussing the differences between the Trapp Family in the movie and what happened in reality. Learn more about the resort, Maria von Trapp, and see some memorabilia from The Sound of Music along the way.

There’s also a really interesting short documentary that shares Maria von Trapp’s memories from her childhood in Austria and throughout her life. During some of the tours, you’ll be able to ask questions to Sam or Kristina when they are on site. This tour is complimentary with your stay at the resort.

Scottish Highland Cows at Trapp Family Lodge

The Trapp Family Lodge owns a herd of Scottish Highland cows (also known as ‘Hairy Coos’ in Scotland!). These cows are known for their coarse, winter coat that’s able to withstand harsh snowy climates like those in Vermont. The cows move from pasture to pasture across the seasons as part of regenerative farming practices.

Of course, in the winter, the cows are fed plenty of hay. Take the complimentary “Meet the Cows” tour to see the cows in person. You do not feed the cows, but you admire them from a comfortable distance away for your safety and the comfort of the cows. They’re so adorable and we had the chance to see some younger cows, too. They’ve all got the best hair!

Downtown Stowe

Downtown Stowe is a walkable and well-preserved historic street with historic buildings and beautiful views. Admire Vermont’s tallest peak, Mount Mansfield, just beyond the town.

We popped into some local shops, like The Country Store on Main, Shaw’s General Store and Stowe Mercantile. Black Cap Coffee is a cute coffee shop. The Stowe Community Church is super photogenic, you’ll have to grab a picture of this towering white building in the middle of town.

Just outside of downtown Stowe, we stopped at Aladdin for lunch, a Mediterranean vegetarian restaurant. They bring a “taste of the Middle East” to Stowe through their pita sandwiches, hummus, baba ghanoush, bowls and mezze platters. I highly recommend trying their hummus and falafel, both were the best that I’d had in a while.

The Alchemist Brewery

The Alchemist Brewery is a family owned and operated brewery in Stowe, focusing on unfiltered IPAs. I immediately noticed the colorful murals painted on the exterior of the building, which continued indoors on the walls and ceilings. This place has such a funky design, so much that I adored the place before I even tried the beer!

The space is divided into a retail area and a beer cafe with ample seating. There’s only one beer on tap (the Hand-Pulled Heady Topper, a double IPA) and the rest you can buy by the can. I’m not so much a fan of hoppy beers myself, so I opted for their Light beer, a Pilsner style brew. While there are some lighter offerings like Light, The Alchemist Brewery tends to offer more IPAs and stouts.

Ben & Jerry’s Factory

In nearby Waterbury, Vermont, visit the only Ben & Jerry’s Factory that’s open to the public. This is their very first factory that dates back to 1985. They still produce 350,000 pints per day at this location. The tours and the original scoop shop haven’t changed much over the years, and that’s simply because there’s no room for improvement.

The guided tours take you past the production floors, and you’ll learn all about how their famous pints are made. Of course, there are samples of ice cream included. Be sure to stop by the Flavor Graveyard to pay your respects to the discounted flavors.

I love Ben & Jerry’s ice cream because they were among the first of the big companies to offer plant-based ice cream. They keep expanding their vegan flavors over the years and they’re equally as innovative as the dairy ones.

At the scoop shop, there are always a few flavors of plant-based ice cream, as well as fully vegan sundaes. I had to get a vegan Oreo sundae with chocolate syrup and whipped cream. It was so decadent! Even though this was a Vermont winter trip, Ben & Jerry’s is seriously tasty in all seasons and weather.

More Activities at Trapp Family Lodge

There are many more places to explore and activities to enjoy at the Trapp Family Lodge. First, I suggest picking up a morning coffee from their Kaffeehaus with indoor seating by the fireplace. Some other activities that are complimentary or included with the resort fee include snowshoeing, yoga, trivia night, a knitting circle, a maple sugar tour, and campfire and s’mores.

There are other classes that have an additional small charge, like wine tastings, painting social, and knitting classes. Take a look at the schedule of activities and events when you check in, and you might fill up your days with interesting things to do.

Vermont Winter Itinerary: Mountain Top Resort (Days 3 & 4)

From Stowe and the Trapp Family Lodge, I ventured to the nearby Mountain Top Resort in Chittenden, Vermont. While this resort doesn’t offer alpine skiing, it’s one of the best places to go snowshoeing and cross-country skiing with rentals available from their outdoor center.

There’s also a restaurant at Mountain Top Resort, as well as Blush Vermont, the day spa. We spent most of our time at Mountain Top Resort to enjoy the amenities, but we also ventured to the nearby communities of Pittsford and Rutland. Here’s how to spend the next two days of my 7-day Vermont winter itinerary.

Stay at Mountain Top Resort (2 Nights)

Mountain Top Resort sits at the top of the mountain surrounded by even more mountains in the Green Mountain range. It’s the perfect mix of exhilarating outdoor fun and both rest and relaxation. Divide your time between adventures and rejuvenating experiences and you’ll have the best stay.

I stayed in one of the Luxury Lodge rooms with large windows to soak up the pretty scenery any time I liked. The rooms have a rustic decor with unique details. For instance, I had a little shelf on my wall that was made out of a little wooden sled.

All overnight guests have access to the cozy sitting area and fireplace in the lobby, the on-site restaurant, and the fire pit. Even if you don’t book a spa treatment, you can use the sauna, fitness room and outdoor hot tub anytime. Book your stay at Mountain Top Resort.

Cross-Country Skiing at Mountain Top

Cross-country skiing is one of the best things to do at Mountain Top Resort. After all, to truly experience Vermont’s winter season, you need to try XC skiing at least once. As it happened, it was my very first time cross-country skiing, so I needed a lesson and equipment rentals.

It’s easy to get fitted for cross-country skis to rent at Mountain Top’s activity center. Then, their expert ski instructor, Maryanne, took myself and my two travel buddies out to the trails. She was incredibly patient and taught us all the basics, adding on new skills, one by one.

After my XC ski lesson with Maryanne, I felt really confident hitting the trails on my own, even if it meant going down some slight downhill sections. If you’re already a cross-country skier, you will love the trails at Mountain Top. There are over 60km of ski trails that are open to the public.

Snowshoeing at Mountain Top

Snowshoeing is another fun winter activity at Mountain Top. Bring your own snowshoes or rent them from the activity center. The staff members will provide you with a map and trail conditions so you can feel confident venturing out into the snow.

Going snowshoeing is such a fantastic way to slowly absorb your surroundings and appreciate the beauty of the forest. Snow clings to the tree branches and the air is so crisp and refreshing.

Like I mentioned earlier, there are 60km of trails at Mountain Top. There are some trails that are groomed trails shared between cross-country skiing and snowshoeing, and others that are snowshoeing only.

Blush Vermont: Spa at Mountain Top

Mountain Top has its own exclusive spa and salon called Blush Vermont. Treat yourself to a massage, facial or nail service during your stay. I had a 50 minute massage at Blush Vermont and it was heavenly. I felt so pampered and relaxed after a morning of cross-country skiing.

Dining at Mountain Top and Beyond

We dined at Mountain Top for breakfast in the Dining Room and for dinner in the pub-style Tavern. In the tavern, there are 12 Vermont craft brews on tap, as well as a wide assortment of innovative cocktails.

For vegan options, there’s a Pad Thai that can be made vegan by subbing out the sauce for a Thai chili sauce. There’s also a vegan black bean burger with fries or truffle fries (leaving off the parmesan).

Baird Farm: Organic Maple Syrup Farm

Baird Farm is a fourth generation family farm in Chittenden, Vermont. It’s a whopping 560 acres with 14,000 maple trees. Over 100 miles of tubing transports the sap into pump stations where it’s pumped directly to their sugarhouse. From there, the sap is boiled down to make the maple syrup we all know and love.

In an average season, one maple tree produces 25 gallons of sap. It’s possible that Baird Farm can gather up to 2000 gallons of sap per hour on one of their sugaring days. You’ll learn about these fun facts and even more on a tour of the farm.

Jacob led us on a tour of the sugarbush where we learned how to tap maple trees and tried it first hand. Essentially, you drill a hole into the tree, put in a little plastic spout, and hook it up to the line of tubes. Then, we toured the production facility with the massive vats that store the sap and other equipment to boil it down to syrup.

My favorite part of the tour? The maple syrup tasting, of course! We got to try eight different varieties of maple syrup. There are the four grades of maple syrup: golden, amber, dark and very dark. The grades of syrup all depend on how early or late the sap is harvested in the season.

My personal favorite is the dark syrup because it tastes the most maple-y, while very dark is one that you’ll only find in Vermont. It tastes really dark, but also a little bit like molasses. I really enjoy this one, too, and you need to travel to Vermont to try it.

The other four flavors are infused maple syrup products: sumac infused maple, spruce tip infused maple, birch bark infused maple and mint infused maple syrup. I’d never tried anything like it! Let me tell you, this Canadian gal was impressed. Baird Farm also had recipes for the ways to use the infused maple syrup products, like cocktails and desserts.

Two Covered Bridges in Pittsford

If you’re taking a road trip to Vermont, you have to visit at least a covered bridge or two! Thankfully for us, there are two covered bridges in nearby Pittsford. Dating back to 1842, the Hammond Covered Bridge is a pedestrian-only covered bridge that you can walk right through.

On the other hand, the Depot Covered Bridge is one that you’ll be able to drive through. The Depot Covered Bridge is one of Vermont’s oldest covered bridges, constructed in 1840. Both bridges span Otter Creek. There are many more covered bridges in Vermont, and you could engineer your road trip to see even more of them.

Greenbrier Gift Shop

For souvenirs and unique gifts, you must go shopping at the Greenbrier Gift Shop. There are hundreds of intriguing treasures that are sourced by the owners of this longstanding business. Discover handmade and locally produced gifts and collections from around the world.

You will find just about anything and everything imaginable in this shop. Jewelry, candles, pillows, gourmet goods, home decor, baby products, purses, bath and body products, and the list goes on. Allow yourself at least an hour to wander through the main rooms and floors of the Greenbrier Gift Shop.

Rutland, Vermont

Rutland is yet another Vermont town with an adorable downtown. Our main purpose of visiting Rutland was to go out for dinner there, but it’s worth stopping by ahead of your dining experience to check out the shops. I really enjoyed visiting Phoenix Books, Divine (clothing store), and I only wish we had arrived before Loose Loona Gifts and Teahouse had closed.

We dined at Roots the Restaurant, a cozy spot situated down a small pathway behind some other buildings in town. Its farm-to-table menu focuses on fresh and seasonal ingredients. Our Fried Brussels Sprouts appetizer was incredible with its sweet chili glaze. I really loved my main course, the Korean barbecue glazed tofu in a yellow curry broth. The service here is top notch, too!

Vermont Winter Itinerary: Manchester (Day 5)

Even though we will be spending the next three nights at Killington, which is a short drive from Chittenden, we’re going to make a detour to Manchester, Vermont. Manchester is about an hour’s drive from Mountain Top Resort, but it’s well worth the drive.

Not only is Manchester a really cute small town with a quaint downtown core, but it’s also home to Hildene, the historic family home of President Lincoln’s son, Robert. As Hildene is closed on Tuesdays and Wednesdays, be sure to plan your trip accordingly.

Hildene, the Lincoln Family Home

Hildene is a historic home owned by the Lincoln family, specifically the son of Abraham Lincoln, Robert Lincoln. Robert and his wife, Mary, built this Georgian Revival mansion as a summer home. It stayed within the Lincoln family until 1975. Lincoln’s great-grandaughter, Peggy lived in the home until her death and eventually the property was saved by a non-profit organization committed to restoring and maintaining Hildene and its artifacts.

We took a guided tour of Hildene to see each room of the home and learn more about the Lincoln family. There are some really unique features within the walls of Hildene, like the organ. It’s the oldest residential pipe organ in America. It’s set up truly as an old fashioned surround sound stereo system. When the keys are pressed, the sound reverberates through the organ pipes on the second floor of the home and throughout the house.

In addition to the rooms of the home decorated with original artifacts and period pieces, there are more exhibits like “The American Ideal”. This focuses on Abraham Lincoln’s words through his second inaugural address. It’s very meaningful when you study and reflect upon each phrase. There are also some museum pieces, like one of Lincoln’s original hats.

Aside from the home, you can also check out the restored 1903 wooden Pullman palace car, Sunbeam. Following the death of George Pullman, Robert Lincoln became president of the Pullman Company, the largest manufacturing company in the world.

Downtown Manchester

Here’s another cute small town to check out on your road trip of Vermont: Manchester! Down the road from Hildene lies downtown Manchester with tons of shops and restaurants to check out.

Don’t miss Northshire Bookstore, one of the largest independent bookstores that I’ve visited in a long time, as well as its book-themed coffee shop, Colburn Cafe. Aunt Bonnie’s is another shop down the road to browse with many gifts and natural remedies. We had lunch at Thai Basil where we were met with delicious food, as well as responsive and fast service.

I also stumbled upon this interesting looking shop called Circa50. I was drawn to the storefront window due to the intriguing pink neon lights. When I looked through the window, what I saw truly surprised me in the best way possible. There were tons of cats lounging around, each with their own heating pad to lay on (though two of the cats were snuggled up on one heating pad, how cute). The shop was sadly closed, but I had to do some Googling and I eventually found the story of the cats.

The Vermont Country Store in Weston

When we read an online review that someone had travelled from four hours away just to shop at The Vermont Country Store, we had to see what was up with it. The Vermont Country Store is a massive shop (it is much larger than it looks from the outside of it) filled with nostalgia and everything under the sun. We visited their location in Weston on our way to Killington.

While The Vermont Country Store has locally made products, clothing, makeup, perfume, bath and body products, grocery items and so much more, it’s really all about taking a trip down memory lane. Where else can you still buy penny candy (that’s literally for one cent)? I saw so many toys and even stickers from my childhood – the ones you scratch and sniff.

You just never know what might catch your eye here. The Vermont Country Store is a worthy addition to any Vermont road trip, whether you’re visiting Vermont in the winter or any time of year.

Stay at Killington Grand Resort Hotel (3 Nights)

I spent the next three nights at the Killington Grand Resort Hotel, conveniently located mountainside at Killington Resort. While you do need to cross a short ski-bridge, this is a ski-in ski-out hotel with a complimentary ski valet service for hotel guests.

My room was spacious and comfortable with its own balcony offering scenic views. There is an on-site restaurant, Preston’s, serving all meals throughout the day, as well as a cafe offering Starbucks coffee and grab-and-go dishes.

When you stay at the Killington Grand Resort Hotel, you’ll have access to the fitness center (with Peloton bikes), an outdoor heated pool and two hot tubs, and an arcade room.

There’s a really excellent shuttle system set up to transport you from the hotel to some restaurants and bars down the road from Killington Resort. Enjoy your night out for apres-ski without needing to worry about transportation!

Vermont Winter Itinerary: Killington Resort (Days 6 & 7)

Our final stop on this Vermont winter itinerary is Killington Resort. We’re spending three nights in total at Killington and will be making ourselves at home here, parking the car and staying put. Our days ahead will be filled with skiing and apres-ski.

Even if you’re a total beginner and have never skied in your life, Killington Mountain Resort is a great destination to give it a try for the first time. There’s actually something for everyone, from beginner to expert skiers. It’s called the “Beast of the East” for good reason – it’s the biggest mountain resort in the eastern USA with six unique peaks.

Skiing at Killington Resort (and Ski Lessons)

Of course, for a Vermont winter trip, you need to go alpine skiing. As I hadn’t gone skiing in nearly six years since my winter trip to Tremblant, I was in desperate need of a lesson. Thankfully, the folks at Killington Resort have excellent small group lessons for beginners.

There were only about six or seven of us learning how to ski with a couple of experienced and knowledgeable instructors who helped us every step of the way (or should I say, every glide of the way?).

We started with some basic instructions and then added on some new skills, like stopping (form a “pizza” with your skis!) or turning left and right. Once we had mastered these basic skills, we set off to the magic carpet to ski down a small bottom portion of the hill.

Our ski lesson lasted a few hours and the instructors were incredibly thorough and patient. We went down that little bunny hill time and time again. Each time, they encouraged us and showed us ways to improve.

If you’ve never gone skiing in your life and you’re intimidated at the thought of putting on downhill skis, please do not worry. The instructors made the experience quite effortless. By the time I got on the chairlift and embarked on skiing down my first green run, I felt super confident and just went for it (albeit, slow and steady!).

Tubing at Killington Resort

Another fun winter activity you can try at Killington Resort is the tubing park. There are several tubing lanes all in a row. Fling yourself down the tubing hill on an inflatable tube. This one is pretty tame by comparison to other ones that I’ve tried in the past, like the epic tubing resort in Quebec, Village Vacances Valcartier. It’s still pretty darn fun!

One of the best parts that you won’t get at any ordinary sledding or tobogganing hill? You don’t need to walk back up the hill! There’s a conveyor system that transports you and your tube back up to the top. Just sit back and enjoy the ride.

Outdoor Pool and Hot Tub

I mentioned earlier that there’s an outdoor pool and hot tub. It’s a 75 foot heated swimming pool that’s open all year long. Yes, it’s suitable to go swimming there, even in super chilly weather. There are also two hot tubs that have warmer water than the swimming pool.

I stayed in the hot tub for most of the time, jumping into the swimming pool to cool off a little bit when I felt too warm. This is the perfect place to visit after a day on the slopes. Rest your sore muscles and relax after an exhilarating day on the mountain. Plus, there are beautiful views of the mountain from the outdoor pool.

Dining and Nightlife

We dined at Preston’s for breakfast and dinner, which was decent fare and conveniently located just steps from my room. We had lunch at two different places: the Long Trail Pub (great for beer, light bites and live music) and the Peak Lodge (burgers, ramen, gorgeous snowy views).

The Peak Lodge is located at the top of the mountain and you’ll need to take a gondola to get there. If you’re a more experienced skier, you can ski down the mountain after lunch, or you can simply ride as a passenger back down the gondola to the base of the hill.

Yama Ramen is a Japanese restaurant down the street from the Killington Resort. They serve up mouthwatering ramen bowls, tasty mushroom bao, edamame and so much more. I love how veg-friendly this restaurant is – definitely try their vegan miso ramen, it was so good!

For apres-ski, head to the Pickle Barrel or the Wobbly Barn for live music. The Wobbly Barn is best to visit on a Saturday night so you can listen to the band. The Pickle Barrel has live music throughout the weekend, so you should head there on a Friday night to enjoy music all weekend long.