The Ultimate Vermont Road Trip

Vermont, one of the northeastern states in USA is bordered to the north by Quebec (Canada), to the east by New Hampshire, to the south by Massachusetts, and to the west by New York. It is one of my favorites states not just in in New England but also the entire United States. Vermont is home to more than 100 19th century covered wooden bridges, is a major producer of maple syrup and boasts of a variety of hiking trails and skiing slopes. This road trip is going to take you through diverse stays and experiences. You will get to stay in a 4-star property, spend some time in a beautiful treehouse, and save some money by staying in some of the wonderful AirBnB properties. You could split this road trip into multiple small visits or go the entire length during the Summer or Fall seasons. What’s more? You will get to explore the wonderful green mountain national forest, a waterfall, a gorge, a covered bridge, a pumpkin patch, a farm, a maple syrup producer, biking trails, hiking trails, brewery tasting, a true speakeasy as well as a harbor. Without further ado, lets get started on this amazing journey.

Day 1 – Killington

A town located in the green mountains of central Vermont, Killington (144 miles from Boston) is home to some wonderful ski resorts, beautiful ‘Thundering Falls‘, variety of flora and fauna, as well as the famous Appalachian trail. We start the road trip by staying at The Red Clover Inn & Restaurant. It’s a historic inn with gorgeous rooms and a wonderful restaurant. Relax and enjoy the property surrounded by nature on all sides before venturing out on your little adventure. Pick apples at Mendon Orchards during Fall, pick up souvenirs at Sugar & Spice, get lost in Vermont’s largest corn maze at Hathaway farm, visit the Vermont Country Store, or visit one of the following museums – Vermont Marble Museum, New England Maple Museum, Billings Farm & Museum. The food at the restaurant is amazing and the bar offers a variety of liquor options. Enjoy your first night cozying up by the fireplace and enjoying a bubble bath.

Day 2 – Woodstock

Woodstock is by far my favorite town for leaf peeping in New England. Only 19 miles from Killington, Woodstock turns magical during Autumn. It has all the elements of your ideal road trip or day trip – Covered bridges, farms, country stores and a stunning gorge. Add to it, the beautiful town center with elegant architecture and numerous restaurants and you have the makings of a perfect itinerary.

Quechee Gorge – Start your day by visiting the Quechee Gorge (in Quechee), also known as Vermont’s little Grand Canyon. The deepest gorge in the state was formed by glacial activity thousands of years ago. You can take in the views from the footbridge or hike the canyon on foot. If you have more time, do explore the Quechee State Park surrounding the region.

Taftsville Covered Bridge – Spanning the Ottauquechee River in the Taftsville village of Woodstock, this historic red bridge is one of the oldest covered bridges in the nation.

Village of Woodstock – Thereon out, it was time to grab some lunch in the Village of Woodstock. We got a lovely window booth at ‘The Bench’ with view of the street. The food was delicious and the local beer was very good.

The Sleepy Hollow Farm – Next we visited the most instagrammable spot in Vermont! The Sleepy Hollow Farm located in Pomfret is one of the most scenic spots in the region. Although it is beautiful year round, autumn is the best time to visit the property. It is a scenic drive to the farm with views of farm animals and a lovely pond.

Cedar Circle Farm – Lastly, we made a stop at the Cedar Circle Farm. We clicked some pictures at the pumpkin patch and picked one up for carving back home!

Day 3 – Saint Johnsbury

Day 3 is all about staying at this beautiful tree house property in Saint Johnsbury. You can book it on AirBnB using the highlighted link and spend a magical night in this epic luxury treehouse. The Outpost Treehouse is a beautifully handcrafted retreat, nestled amongst the evergreens atop Spaulding Mountain and adjacent to the nationally renowned Alerin Barn event venue. It is located 0.5 mile from Stephen Huneck Gallery/Dog Mountain, 3 miles from the historic Town of St. Johnsbury, in the heart of Vermont’s North East Kingdom. Mountain Bikers are just over 10 miles to The Hub at Kingdom trails, 15 miles to Burke Mountain ski and bike park, and you are 2 exits north from Littleton & White Mountains in New Hampshire. We were surrounded by the woods on all sides and spent most of our time enjoying this splendid and creative property with a glass of wine by the fireplace.

Days 4 & 5 – Stowe

I have visited Stowe in both Summer & Fall and it has by far been my favorite town in Vermont. Overlooked by Mount Mansfield and home to the Smugglers’ Notch State Park, Stowe is an year-round destination for all visitors. Whether you want to go hiking and swimming in Summer, or leaf peeping during Fall or skiing during Winters, Stowe is the ideal Vermont town!

Bingham Falls – Take a short hike down to this lovely waterfall and take a dip in the crystal cool waters of this natural swimming hole!

Stowe Pinnacle Hike – A moderate 3.6 miles hike at an elevation of 1520′ leads to one of the most spectacular views in the town. At the summit, you will be surrounded by majestic views of the Camel’s Hump, Mount Mansfield, the Worcester Range and the Sterling Range. I came across a tepee on my way up and loved taking pictures around it.

Bike the Stowe Recreation Path – A paved greenway stretching from Stowe Village to Top Notch Resort on the Mountain Road. This 5.5 miles paved public path is free to use and offers some gorgeous views along the way. People use it for hiking, biking, running and even for skiing during winters. We crossed a corn maze, a garden, some bridges (spanning a river), picnic tables and mountain views from various stops.

Mount Mansfield – Mount Mansfield, located in Chittenden County within the Green Mountains is the highest mountain in Vermont with a summit that peaks at 4,395 feet above sea level. On a clear day, the summit offers beautiful views of Lake Champlain and the Adirondack Mountains. You can drive to the summit using the historic auto toll road or hike the 7.3 miles Mount Mansfield Loop Trail open year round. Fun Fact: There is also a 108 mile hiking trail leading in to Canada from the summit.

Trapp Family Lodge – A luxury resort with Austrian inspired architecture, it’s a vast property spread out at a prime location in the town. Trapp Family Lodge is owned and operated by the family behind the movie ‘The Sound of Music’. We bought a day pass to explore the property and have some breakfast. The Austrian bakery ‘Kaffeehaus‘ had some beautiful views and limited but good breakfast . We even spotted some farm animals on the way to the bakery. We came back to the ‘Bierhall‘ (brewery) later in the evening and enjoyed good beer with delicious sausages and schnitzels. Another notable brewery to visit would be the Idletyme Brewing Company.

Nebraska Knoll Sugar Farm – Nebraska Knoll Sugar Farm is family owned and operated by the Coty family. Each spring since 1980, the Coty family, have tapped 9000 sugar maples in the foothills of Mt. Mansfield. You can tour the farm, sample and buy maple products from their lovely store.

Some fun things to do in the neighboring town of Waterbury:

Cold Hollow Cider – Try the cider donughts.

Vermont Artisan Coffee & Tea – Try the maple flavored coffee and buy some for home.

Ben & Jerry’s factory – Tour the factory and try some fresh ice cream made on the spot.

Recommended AirBnBs I have stayed in:

Waterbury: https://www.airbnb.com/rooms/44946133?source_impression_id=p3_1649438890_DXNHwc5IErD6LTzI

Morristown: https://www.airbnb.com/rooms/40815511?source_impression_id=p3_1649438837_GWJBdKASSp49VIt7

Fun Fact: The VT 100 route (scenic route 100 byway) which you will be taking a couple of times during your stay in Stowe is gorgeous, surrounded by rolling greens, barns and if you get lucky, plenty of farm animals and wildlife!

Days 6 & 7 – Burlington

The most-populous city in Vermont, Burlington is located in northwestern Vermont, on the east shore of Lake Champlain, south of the Canadian border. The vibrant downtown has plenty of restaurants, a thriving art scene and quite a few live performances.

Church Street Marketplace – Lovely outdoor cafes, street vendors and entertainers. Quite lively and fun! Do enjoy the maple creemee from any of the vendors and you will thank me later!

Red Square Burlington – Late-night hot spot for DJs, drinks, dancing & an eclectic lineup of live bands.

Burlington Greenway Bike Path – Situated on the Lake Champlain shoreline, it is 8 miles of paved path which is part of the longer Island Line Trail. Linking 6 major waterfront parks, Burlington Bike Path offers beautiful views of the lake and the Adirondack mountains.

Light Club Lamp Shop – Vintage Lamps, live music, theatre, community events, food and drink, puppetry and poetry, lamps, plants and dance floors, Bean and Lamp Shop classics.

Lincolns Burlington – First speakeasy experience of my life. Let’s just say it wasn’t easy finding this one. However after we got in, hello super affordable cocktails and good food!

Waterfront Park – Enjoy the sunset at harbor front. Apart from offering magnificent views, this park also hosts music festivals and other community events.

I hope you enjoy this road trip as much as we did and make the most of your time in the lovely state of Vermont!