Vermont may not be the largest state in New England, but it has a lot to offer. Not only is Vermont a wonderful place to visit year-round, but it is most popular for the fall foliage. A great way to explore this state is to hit the road on one of the many scenic road trips in Vermont. This is especially the best way to experience the breathtaking beauty of Fall in Vermont.
Best Road Trips & Scenic Drives in Vermont
Connecticut River Byway
Traveling along Route 5, the Connecticut River Byway goes from southern Vermont to northern Vermont ending on another National Byway. It is a three-state, 500-mile byway. This byway spans from Massachusetts through both Vermont and New Hampshire all the way to the Canadian border.
Meandering through this byway promises historic river towns, acres of farmland, and beautiful river views. The most popular stretch would be the 128 miles on Route 5 from Brattleboro to St. Johnsbury, Vermont. Of course, you can drive all the way to Canada or make it a road trip to Canada.
Road Trip Stops Along Connecticut River Byway
Latchis Hotel & Theatre in Brattleboro: This hotel opened in 1938 in downtown Brattleboro. It is the only Art Deco hotel in Vermont. Coming from Miami, I do love exploring Art Deco hotels! Additionally, the Latchis Theatre is a fun spot to see movies. It is a member of the League of Historic American Theaters.
Westminster, Vermont: Chartered in 1735, enjoy Vermont’s oldest town. This tiny village is nearly entirely listed on the National Register of Historic Places.
Mount Ascutney State Park: Vermont is known for its incredible nature and outdoor spot. This spot has unique hiking trails and family-friendly campgrounds. It is truly the spot to be for nature lovers and outdoor adventurers.
King Arthur Baking Company: Started more than 200 years ago, this is America’s first flour company. The flagship store is located in Norwich. In store you can stock up on baking supplies, have a fresh lunch, or even sign up for a class at the King Arthur Baking School.
Dog Mountain in St. Johnbury: Dog Mountain is set on the top of a private mountain in St. Johnsbury. The grounds are always open to people and their dogs. Head over to the Dog Chapel to pay tribute to dogs loved and lost.
Covered Bridges of Bennington County
Fun Fact about Vermont is that this US State has the densest concentration of covered bridges. There are over 100 scattered throughout the state. These structures offer many opportunities for lovely pictures and road trip inspiration.
Bennington County in the southwestern part of the state is the best place to go drive through these scenic bridges. Starting in the town of Bennington you’ll immediately head north and come up to 5 classic, red-painting “kissing” bridges. Along this drive, you’ll go through the oldest covered bridges which dates back to 1852.
Bridges to See in Vermont
West Arlington Bridge: Built in 1852 and on the National Registry this bridge is the most photographed bridge in Vermont. It spans over the Battenkill River near the Chapel on the Green and down the street from Norman Rockwell’s old house.
Cornish-Windsor Covered Bridge: In 1886, this bridge was built to connect New Hampshire and Vermont. Until 2008, this bridge was the longest bridge at 449 feet.
Silk Road Covered Bridge: Built in 1840, this bridge spans the Walloomsac. There are a couple of trails both to the north and south to give you a better view of the bridge.
Paper Mill Covered Bridge: One of the newest bridges in Vermont. Built to replace the bridge in 1889. It spans 122 feet along Murphy Road. It is named after Vermont’s first paper mill in the area.
Chiselville Covered Bridge: Built in 1870, this bridge is notable for several reasons. It sits 40 feet over the Roaring Branch River. It spans 117 feet and had a brief moment of fame in the movie Baby Boom. Finally, this is a great bridge to walk across to get the full experience.
Crossroads of Vermont Byway
This 41-mile Vermont road trip goes from east to west right through the middle of the state. It crosses through the Green Mountains. It can be completed in a single day, or it can be made into a weekend trip.
Rutland can be a great place to start this trip. A premier destination for art lovers, this town is a great place to start moving east. Then, you’ll make it through many mountain towns, such as Mendon, Killington, and Bridgwater, before making it to Woodstock and Quechee.
If you decide only to make one day of this road trip, definitely stick in Woodstock for a while, as there is so much to do! Since you’ll be driving through the mountains, the relaxing drive will give way to so many changing leaves you’ll feel like you are in a whole different world. Another great way to see the leaves up close is in Quechee. Quechee Gorge Bridge on Route 4 carries vehicles and pedestrians over this splendid fall scene. Even better: Park and walk the Quechee Gorge Trail for an up-close look.
Stops Along the Crossroads of Vermont Byway:
Killington, Vermont: Killington is truly an outdoor paradise. There is hiking, swimming, and even skiing. It is one of the most popular places to ski in New England.
Long Trail Brewing Company: One of Vermont’s oldest breweries. Definitely a must-visit for all brewery enthusiasts.
Billings Farm & Museum: Located just outside of Woodstock is this farm & museum. Vermont is known for its cheeses, butters, and milks so this museum combines an award-winning Jersey dairy farm with the best outdoor history museum in the country.
Quechee Gorge: Nicknamed “Vermont’s Little Grand Canyon” at 165 feet deep. It is the deepest gorge/canyon in Vermont.
Green Mountain Byway: Loop
Part of the larger and more well-known Route 100 road trip, this scenic Vermont trip is 71 miles. It is one of the most scenic drives in all of New England. Truly the best place for leaf peeping in the fall!
Set against the dramatic landscape of the jagged peaks of the Northern Green Mountains contrasted with the open farmland, it makes for an exceptional view. Many historic towns dot the landscapes. They have worked together to create unique communities for locals and visitors alike.
This byway starts in Waterbury traveling south through Stowe, Morrisville, Johnson, and Cambridge. Along the way, you’ll drive through the famous Smuggler’s Notch, see gorgeous waterfalls, and obviously stop for some tasty Vermont snacks! This loop is by far the best, with a whole weekend ahead to really relax and enjoy the many stops and views.
Stops along the Green Mountain Loop:
Ben & Jerry’s Factory: A fun place to see how ice cream is made. Check out the flavor graveyard and grab a scoop of the most famous ice cream from Vermont.
Cabot Farmers’ Store: Head over here to get some Vermont cheese.
Cold Hollow Cider Mill: While still in Waterbury, head over to this cider mill to learn how cider is made. Definitely have a donut or while here.
Mount Mansfield: The tallest peak in Vermont! Drive to the top to see the views. Additionally, hike along the ridge.
Bingham Falls: A short hike leads to the beautiful Bingham Falls off Route 108 in Smuggler’s Notch. It is also a swimming hole!
Jericho to Stowe Through Smugglers’ Notch
Smugglers’ Notch is Vermont’s best-known mountain pass. Starting at the Old Red Mill in Jericho, then going east on Route 15. This mountain pass is definitely one of the best places to experience the Vermont Fall.
Passing through Underhill, which has Vermont’s highest peak, Mount Mansfield. Route 15 then heads north to Cambridge, following along the Lamoille River towards Jeffersonville. From here, merge onto Route 108 for another incredible road trip through Smuggler’s Notch.
This narrow passageway served as a smuggling route for illegal goods from Canada twice in its history. It is truly thrilling to drive through these mountains.
Pro-Tip: Route 108 is closed from mid-October through mid-May. Take this into consideration when you’re looking to go for a leaf-peeping adventure. Route 15 is an option to make your way back to Route 100.
Smugglers’ Notch Stops:
Old Red Mill: Found in Jericho and dating back to the 19th century, this mill has been a fixture on the Browns River. It is home to the Jericho Historical Society.
Barnes Camp: Located at the southern foot of Smugglers’ Notch is the first stop visitors can get to, providing all sorts of information on the best pullouts and picnic areas.
Cambridge, VT: There are three covered bridges in this area, which add to the magic of fall.
Lake Champlain Byway
This byway is longer, in its entirety it spans 185 miles going all the way to the Canadian Border. However, it is a very soothing 185 miles with farmland all around and the Adirondacks and Green Mountains making up the backdrop. This trip has something for everyone!
It’ll take you around Vermont’s largest lake, through Vermont’s biggest city, or allow you to get lost in the wild backroads. Starting in Vergennes, Vermont’s smallest city, drive north on Route 7 to Burlington.
As a longer byway, I recommend making it a several-day long road trip in Vermont. Burlington is a great city. Make the first stop, as there is so much to explore. Additionally, the road will allow you to spend time exploring Lake Champlain Islands, which include Vermont’s first commercial winery and an ancient coral reef. Below are some more options for stops along the way.
Stops for your 2-3 Day trip:
Lake Champlain Maritime Museum: Learn all about Lake Champlain’s fascinating maritime history with both indoor and outdoor exhibits.
Mount Philo State Park: Drive or climb to the top of Mount Philo in Vermont’s oldest state park.
Shelburne Museum: This giant museum includes multiple historic buildings, indoor and outdoor exhibits, and over 150,000 items in the art collection!
Church Street Marketplace: Found in Burlington, this pedestrian-only outdoor shopping and dining center is the place to be!
Snow Farm Vineyard: Vermont’s first commercial winery. They offer tastings as well.
Mad River Byway
Another short Vermont road trip that covers another section of Route 100 and 100B. If you’re not interested in doing the entire Route 100 trip but want to make this one a little longer, consider combining it with the Green Mountain Byway.
Mad River Byway is an ideal day trip! This one is definitely better to do in summer rather than fall, but don’t be confused, the leaf peeping here is also spectacular. The reason we recommend coming in the summer is that there are so many swimming holes and hikes to take advantage of while here.
Best Stops Along this Byway:
Mad River Taste Place: A specialty grocery store with incredible Vermont products. It’s a great place to stock up on supplies for a fun-filled day. Get some cheeses, meats, maple syrup,, and more.
Warren Falls: One of the best swimming holes in Vermont. It is located right off Route 100. It has shallow spots for kids, deep spots for cliff jumping, and, of course, beautiful waterfalls.
Mad River Path: There are numerous continuous public pathways and trails connecting Warren, Waitsfield, Fayston, and Moretown. They vary in levels of difficulty, but are a great way of exploring the area.
Molly Stark Byway
Another short road trip that can easily be a day trip or extended to a weekend getaway. Beginning at Bennington, Molly Stark Byway travels through the Green Mountains and on Route right through Woodford, Wilmington, and Brattleboro.
This area gives you the perfect mix of history, art, and outdoor activities. In order to explore all the sites, you’ll want three days.
Sites to see along the way:
Woodford State Park: rent a kayak, go for a swim, or go for a hike around the lake.
Wilmington: Explore the downtown area, get some food at the many different options, and explore Lake Whitingham.
Hogback Mountain: This mountain has an incredible 100-mile view that is absolutely worth the stop!
Northeast Kingdom Byway
For the Wildest places in Vermont, head over to the Northeast Kingdom byway. It has some of the most beautiful landscapes in the country. Featuring lush, impenetrable forests, lakes, and large farmsteads, it is truly a special place.
This piece of paradise is found in the 51 miles between St. Johnsbury and Newport. Through here, you’ll see the small towns of Lyndon, East Burke, West Burke, Westmore, Charleston, and Derby.
This is the road trip for all nature lovers! Be on the lookout for moose and deer. You’ll want at least two days to really enjoy this road trip in Northern Vermont.
IMPORTANT: There is lousy cell service and unpredictable weather. Make sure people know where you are in case you lose contact for extended periods of time.
All the Stops Along Northeast Kingdom Byway:
Kingdom Trails: 100+ miles of trails that have become the premier mountain biking destination. This trail is unique and gives the most spectacular fall foliage backdrop to all outdoor activities.
Lake Willoughby: Vermont’s deepest lake and one of the prettiest. The two mountains on either side give the feeling of a fjord. Additionally, climb to the top of Mt. Hor for some stunning views.
Route 100
By far the most popular road trip route in Vermont. It runs north to south down the center of the state, giving you the most complete view and experience of Vermont.
Starting in Wilmington north to Granville, this is the best route for fall foliage in New England. Two to three days should be more than enough to explore this road trip if you want more time to walk around and wander, stick to three days.
Route 100 starts near the Molly Stark Byway and connects with the Mad River Byway in Warren. There are historic inns, farms, picture-perfect towns, and eclectic shops along the way. It would truly be a disservice not to check out this road trip.
Spectacular stops along Route 100:
Mount Snow: A great place to go skiing in winter. Definitely one of the best ski spots in New England. In summer and fall, you can take the Bluebird Express to the top of the mountain to explore.
Jamaica State Park: For all your favorite outdoor activities. Swim in the river or ride a bike on the West River Rail Trail.
Vermont Country Store: The most iconic country store in Vermont! Come sample some Vermont cheeses or get yourself flannel.
President Calvin Coolidge Historic Site: Explore the birthplace and childhood home of this country’s 30th president. The whole town appears to have remained the way it was when Coolidge was a child.
Moss Glen Falls: One of Vermont’s prettiest waterfalls. It is right off Route 100 in Granville.
Mount Bromley Overlook: An incredible vista of the Green Mountains. It is particularly magical in the fall with all the best fall foliage.
Shires of Vermont Scenic Byway
Southwest Vermont boasts this scenic byway. It is a pastoral road trip through Vermont that winds through a narrow valley between the Taconic Mountains and the Green Mountains. Bennington is a great place to start, as it’s also the start of the Molly Stark Byway.
Driving north on Route 7A will take you through historic towns and farms. Additionally, be aware of the dirt and gravel side roads, which might tempt you with extra exploration. This 23-mile road trip will bring you through some gorgeous fall foliage.
Stops Along the Shires of Vermont Byway:
Old Bennington: If you choose to start in Bennington, spend a little time through a self-guided tour in Old Bennington. This will take you through the Bennington Monument, Old First Church, and the Bennington Museum.
Lake Shaftsbury State Park: In the summer, this park has a great lake for swimming as well as a one-mile trail around the lake.
Hildene, Manchester: The former summer estate of Robert Todd Lincoln, son of President Abraham Lincoln. The grounds are incredible and well worth a visit. You can take a tour of the house as well.
Southern Vermont Arts Center: Also in Manchester, it is home to the largest outdoor sculpture park in Vermont.
Stone Valley Byway
Where the Shires of Vermont Scenic Byway leaves off, the Stone Valley byway picks up. Through here, you have the opportunity to learn about America’s most notable marble and slate quarries.
Some of the quarries are abandoned and are now used as popular swimming holes like Dorset Quarry. Others can only be accessed via hiking trails like Gettysburg Quarry.
As you make your way to Hubbarton on this trip, you can truly enjoy the changing leaves and the beautiful scenery of Vermont. This route winds along Route 30 for 43 miles. It is a perfect day trip.
Stops along the Stone Valley Byway:
Dorset Quarry: Driving along Route 30 in the summer, this is the perfect stop. Refresh yourself in the new swimming hole.
Gilbert’s Lookout Hike: If a swimming break isn’t your speed or it isn’t summer, do some leaf peeping in the Dorset Town Forest. The best hike is Gilbert’s Lookout, which has incredible views and several abandoned marble quarries.
Lake St. Catherine State Park: Another park to enjoy nature and lake activities. Rent a kayak or canoe or take a dip in the waters of Lake St. Catherine.
Hubbardton Battlefield State Historic Site: The only battle of the Revolutionary War fought in Vermont took place here. The Battle of Hubbardton on July 7th, 1777.
The Vermont Cheese Trail
Vermont is known not only for its world-class cheese producers like Cabot but also for many small artisan cheese-makers. A delicious road trip in Vermont is to use the Vermont Cheese Council’s Cheese Trail map. This will take you through all the many cheese farms and factories open to the public in Vermont.
With all the cheese tasting and purchasing on this trip, you may want to pack a cooler. This is a great day trip to make the most of Vermont’s cheeses.
For the ultimate cheese experience, check out the stops below:
Crowley Cheese: The oldest continuously operating cheese factory in the country! You can see how cheese is made using traditional methods and hand tools. Additionally, their hand made cheddar cheese is for sale along with many others in their shop. A must-stop for all cheese lovers.
Vermont Farmstead Cheese Company: Winners of the 2021 international cheese competition, you truly cannot get more farm-to-table than here. Sample and buy all your favorite cheeses.
Quechee General Store: A great place to go for Vermont favorites like local honey, maple syrup, Vermont coffee, and all sorts of artisanal cheeses. It is a great place to stock up on all sorts of local Vermont goodies for a road trip.
A Vermont Island Drive
Driving up Route 1 out of Burlington, you can take on an island adventure. Through the islands in Lake Champlain, this is a great addition to the Lake Champlain Byway drive. This road trip is particularly enjoyable in Vermont summers.
Lake Champlain is frequently considered the sixth great lake! It is truly a must-go lake in New England. While many of the stops for this road trip are similar to the ones in the Lake Champlain byway, such as the Snow Farm Vineyard or the Alburgh Dunes State Park. The different islands have many more things to offer.
Stops Along the Lake Champlain Islands
South Hero Islands, AKA Grand Isle: Along with Snow Farm Vineyard, there are many great places to dine on Hero Island. Hop over to its neighbor to North Hero Island for some more places to eat. Head over to Allenholm Farm for a petting zoo or apple picking in the fall.
Isle Lamotte: Vermont’s oldest settlement, Isle Lamotte, originally built to protect Montreal, now has the most popular shrine to St. Anne. Additionally, the Fisk Quarry Preserve and the Goodsell Ridge Preserve are incredible places to visit or hike due to the oldest known coral fossils. The limestone there is so dark in appearance that it was originally marketed as Black Marble.
Alburgh: The gateway from Vermont into Canada. Here is where you find the Dunes State Park for a refreshing beach to go for a swim in the lake.
White River Junction to Reading
This is the absolute best Vermont road trip for those who want the quintessential Vermont Fall pictures. It is a trip for all the photographers. Start in White River Junction and head west on Route 4.
There are many stops along the way that will make you want to pull over to get all the pictures of the leaves turning colors or glowing in their fiery oranges, reds, and yellows. Driving through Quechee Gorge, stopping at Taftsville Covered Bridge, and then rolling into Woodstock.
While Woodstock can be a trip on its own, if you are not planning an overnight trip, don’t be lured in by all the places to take pictures here. There are covered bridges, Jersey Cows, and beautiful gardens.
Now, the best part of the trip is going south to Reading on Route 6. Here, you’ll pass by the most photographed farm in New England. The trip continues through Route 106, then only Route 131, and onto Route 100 before getting back onto Route 4.
Photography Stops
The best way to show this is with a map of the stops, so here it is!
Final Thoughts About Road Trips in Vermont
Vermont is a truly magical place to visit in the fall. However, Vermont has so much to offer year-round. Between skiing, swimming, and leaf peeping, it is a must-visit state in New England. When we lived in Boston, we loved getting away to Vermont for slower, more relaxing weekends. Plus, there is nothing like seeing the leaves turn colors as seeing it on the mountain.
