Vermont Road Trip

The Perfect 5 Day Vermont Road Trip During Winter 2024

Dreaming of a perfect winter vacation in Vermont? After spending countless days exploring the beauty of Vermont, I’ve put together a road trip itinerary that’s all about the best of Vermont. Trust me, Vermont road trip is an experience like no other.

How long does it take to visit Vermont? Well if you ask me, I would say you can spend a decade here, but Five days is just right if you have a limited time.

This itinerary includes a mix of driving, exploring, and relaxing. We’re talking about 2 to 3 hours on the road daily, giving you plenty of time to soak in the sights and sounds without feeling rushed.

I’ve mapped out a plan for five action-packed days. But, if you’re the type who likes to take it slow, feel free to stretch each day out. There’s so much to see and do, from hidden corners to popular spots, and taking your time means you will get all the things.

In this guide, I’m sharing the best places in Vermont to visit. Whether you’re here for the skiing, the scenery, or the small-town charm, this road trip has got you covered. Let’s dive into the beauty of Vermont and make some unforgettable memories!

Is Winter a Good Time to Go to Vermont?

Is winter a good time for a Vermont trip? Of course it is going to be very cold, but that’s what makes it special. Vermont in winter is like stepping into a snow-filled fairy tale.

things to do in Vermont

Vermont has some of the best ski spots around – Stowe, Killington, you name it. The snow here is just right for skiing and snowboarding. But if you’re not into skiing, there’s still plenty for you. You can go on sleigh rides, sit by a warm fire in a cozy inn, and walk through streets that twinkle with lights.

There are festivals and outdoor fun that make the cold weather worth it. So, is winter a good time to visit Vermont? If you’re up for the beauty and fun of a snowy wonderland. Just come prepared, and you’ll have the time of your life.

How to Plan Your 5-Day Vermont Road Trip?

Planning a 5-day road trip through Vermont in winter is an adventure you’ll always remember. Here are some practical tips to plan your trip and to make the most of it:

  • Winter in Vermont is magical from December to early March. Consider visiting during these months to experience the best of Vermont’s winter wonderland.
  • Vermont offers a range of stay options, from cozy bed and breakfasts to luxury resorts. Book early, especially if you plan to visit popular ski destinations like Stowe.
  • Start in Burlington and walk through Stowe, Montpelier, Woodstock, and Bennington. This route covers a mix of urban charm and rural beauty.
  • Rent a car suitable for winter driving. A 4WD vehicle with snow tires is recommended.
  • Pack for cold weather, thermal layers, waterproof outerwear, and insulated boots are essential. Don’t forget gloves, scarves, and hats.
  • You can bring your own gear or rent at the resorts if you’re skiing or snowboarding.
  • Research and list the places you want to visit in each town. Include a mix of outdoor activities, cultural sites, and local eateries.
  • Winter days in Vermont are shorter. Plan to start your activities early to make the most of the daylight.
  • Vermont hosts several winter festivals and events. Check the local calendar to see if you can align your trip with these events.
  • Winter weather can be unpredictable. Have a flexible itinerary in case you need to change plans due to weather conditions.

5 Day Vermont Road Trip In Winter

Here’s a detailed 5 day guide to make sure you hit the highlights and enjoy every moment:

Day 1: Exploring Burlington

Begin your Vermont adventure in Burlington, It is the largest city known for its vibrant culture and beautiful lakeside views. There are plenty of fun things to do in Burlington.
Start with breakfast at one of the local cafes on Church Street. I recommend trying a place like Penny Cluse Café, where the pancakes are a must-try.

church street marketplace

Spend your afternoon strolling along the Church Street Marketplace. This pedestrian-only street is perfect for shopping and people-watching.

For lunch, grab something from a local eatery. The Farmhouse Tap & Grill is a great spot for farm-to-table fare.

As evening sets in, consider visiting the waterfront for a scenic sunset view. For dinner, head to a restaurant like Hen of the Wood for a true taste of Vermont’s local cuisine.

Overnight in Burlington. There are several cozy inns and hotels downtown. The Hotel Vermont comes highly recommended for its local charm and great location.

Day 2: Exploring Stowe

Stowe is a charming town in the Green Mountains, it is famous for its skiing and outdoor activities. Beyond its snowy slopes, there are many things to do in Stowe. It is filled with quaint shops, art galleries, and cozy eateries, all set against stunning mountain scenery.

Start your day with a scenic drive from Burlington to Stowe, which takes about an hour. The route itself is picturesque, especially with the morning light.

Once in Stowe, begin with a visit to the Trapp Family Lodge. This iconic spot offers breathtaking views and a unique history – it’s the former home of the von Trapp family of “The Sound of Music” fame.


After soaking in the views at the Trapp Family Lodge, head to Stowe Mountain Resort. Whether you’re into skiing or snowboarding or just want to enjoy the mountain atmosphere, it’s the place to be.

For lunch, try the resort’s Cliff House Restaurant. Located on the mountain, it offers great food with an even better view. In the evening, explore the town of Stowe. The streets are lined with unique shops and galleries, perfect for an evening wander.

For dinner, The Bench is a great option with a relaxed atmosphere and a menu that has something for everyone.
Spend the night in Stowe. Consider staying at the Green Mountain Inn for its cozy charm and convenient location.

Day 3: Montpelier and Surrounding Areas

Montpelier is the capital of Vermont. It maybe the smallest state capital in the U.S., but it’s big on charm. This city exudes a quaint, almost storybook feel with its historic buildings and friendly community. Montpelier is a hub for arts and culture and is surrounded by natural beauty which makes it a peaceful yet intriguing stop on your road trip.

Begin your day with a drive to Montpelier. The journey from Stowe is short and scenic, taking about 45 minutes.
Once you arrive, a visit to the Vermont State House is a must. It’s a beautiful, historic building with a rich history.

After soaking up some history, head to Morse Farm Maple Sugarworks. This place is all about authentic Vermont maple syrup. You can tour the farm, learn about syrup production, and taste different varieties.

Morse Farm Maple Sugarworks

For lunch, check out Kismet in downtown Montpelier. Their farm-to-table approach ensures fresh and delicious meals. Spend your evening exploring downtown Montpelier.

For dinner try Sarducci, it offers a great Italian meal in a cozy setting by the river. Stay overnight in Montpelier. With its classic New England style, the Inn at Montpelier offers a comfortable and charming stay.

Day 4: Woodstock and Surrounding Areas

Woodstock is often hailed as one of the most picturesque towns in New England. With its covered bridges, colonial homes, and charming downtown, it’s a postcard comes to life. This town embodies the essence of rural Vermont with its rolling hills, scenic farms, and a tranquil atmosphere.

Start with a drive to Woodstock from Montpelier. The trip, taking about an hour, is as beautiful as the destination itself.
Once in Woodstock, a visit to the Marsh-Billings-Rockefeller National Historical Park is a great way to start.


Spend your afternoon at the Billings Farm & Museum. This working farm offers a glimpse into Vermont’s rural past and present. It’s both educational and scenic. For lunch, try the Woodstock Farmer’s Market. They have an array of local, fresh foods that you can enjoy right there or take with you for a picnic.

In the evening, take your time wandering through downtown Woodstock. The shops and galleries here are full of local treasures.
For dinner, The Prince and the Pauper restaurant offers a delightful dining experience with its seasonal menu.

Overnight in Woodstock. The Woodstock Inn & Resort, known for its elegance and comfort, is a perfect place to relax after a day of exploration.

Day 5: Bennington and the Journey Home

Bennington is located in Southern Vermont. Bennington has a rich taste in history and arts. It is mostly known for its beautiful old buildings, museums, and the iconic Bennington Battle Monument, it’s a town that beautifully wraps up your Vermont road trip with a taste of history and culture.

Bennington Battle Monument

Your journey to Bennington from Woodstock will take about two hours, but the drive is part of the experience, with beautiful landscapes.

Start your Bennington adventure with a visit to the Bennington Battle Monument. It’s historically significant and offers great views from the top. After the monument, head to the Bennington Museum, known for its collection of Grandma Moses paintings and Vermont historical artifacts.

For lunch, try the Blue Benn Diner, a classic diner experience with a vast menu to satisfy any craving. Spend your late afternoon strolling through downtown Bennington.

For your final dinner, consider The Grille at Mt. Anthony Country Club for a meal with a view.
If you’re not heading home immediately, consider staying overnight at the Four Chimneys Inn, which offers a quaint and comfortable stay.

Bennington’s blend of historical significance and cultural richness provides a fitting end to your Vermont winter road trip. As you head home, you’ll carry with you the memories of snow-covered landscapes, cozy town streets, and the warm hospitality of Vermont.

5 Day Vermont Road Trip Conclusion

I hope you feel excited and ready to plan on this beautiful journey. Vermont in winter is truly a special place, offering a blend of outdoor adventure, cultural richness, and breathtaking landscapes.

From the vibrant streets of Burlington to the quaint charm of Woodstock, each day of this trip is set to bring new experiences and memories. Whether you’re gliding down the slopes in Stowe, exploring the historic sites in Montpelier, or enjoying the serene beauty of Bennington, Vermont offers a winter experience unlike any other.

Just make sure to plan well before you go. It is going to be very cold, so pack yourself with multiple layers.

In case you missed my recent blogs, do check them below.

Vermont Road Trip FAQs

What should I pack for a Vermont winter road trip?

Bring layers like thermal wear, fleece jackets, waterproof outerwear, and insulated boots. Don’t forget accessories like gloves, scarves, and hats. If you plan to ski or snowboard, consider bringing your gear, or you can rent it at the resorts.

How are the road conditions in Vermont during winter?

Winter roads can be snowy and icy. Most main roads and highways are well-maintained, but it’s wise to have a 4WD vehicle and be prepared for winter driving. Always check the weather forecast and road conditions before heading out.

Is it easy to find accommodations?

Book in advance, especially during peak winter months. Vermont offers a range of options from cozy B&Bs to luxury resorts. Consider staying in different towns to experience the variety Vermont has to offer.

Are there winter activities for non-skiers?

Absolutely! You can enjoy sleigh rides, winter hiking, snowshoeing, and exploring the charming towns. Many places offer spa services, and there are plenty of museums and historical sites.

What are some must-try local foods in Vermont?

Vermont is famous for its maple syrup, so anything maple-flavored is a must-try. Also, sample the local cheeses and dairy products, fresh-baked goods, and if you’re into craft beers, Vermont has a fantastic selection.

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