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The Most Beautiful Vermont Scenic Drives: 10 Designated Byways

Planning a New England vacation and looking for a few beautiful Vermont scenic drives? Want to fill your days with far-reaching vistas, pastoral landscapes, and opportunities for outdoor recreation?

Fill up your gas tank, charge your camera, and pack your sturdy footwear — it’s time for another incredible Vermont road trip!

A collage of photos featuring Vermont scenic byways.
Vermont’s back roads are hard to beat!

Whether you want to get away for a week or an afternoon, these 10 incredible byways are the most scenic drives in Vermont, encompassing everything you love about Vermont road trips, no matter what season you choose to take them.

Connecticut River Byway: Brattleboro to St. Johnsbury

2-3 days, 128 miles

The Cornish-Windsor Covered Bridge over the Connecticut River.
The Cornish-Windsor Covered Bridge across the Connecticut River

Travel 410 miles along the Connecticut River from one end of Vermont to the other on Vermont’s only designated National Byway.

The Connecticut River Byway is a three-state, 500-mile byway, spanning the west and east shores of the Connecticut River starting in Massachusetts and traveling north through Vermont and New Hampshire to the Canadian border.

A journey on this meandering stretch of pavement includes far-reaching river views, historic river towns and cities, and acres of fertile farmland. We recommend taking a weekend trip and driving 128 miles on Route 5 from Brattleboro to St. Johnsbury, Vermont, but of course, you can drive all the way to Canada if you have time.

The Connecticut River Byway is one of the most scenic drives in Vermont, with ample opportunities for extending your vacation.

The Latchis Hotel on a rainy evening.
The Latchis Hotel on a rainy evening

Here are some of the stops we’d recommend on this beautiful Vermont road trip:

  • Latchis Hotel and Theatre, Brattleboro: The Latchis Hotel opened in 1938 in downtown Brattleboro. It’s Vermont’s only Art Deco Hotel. The Latchis Theatre, right downstairs, is a member of the League of Historic Amerian Theatres and a fun spot to see Hollywood’s latest films.
  • Westminster, Vermont: Stop and enjoy Vermont’s oldest town, chartered in 1735. Most of the tiny Westminster Village (population 287) is listed on the National Register of Historic Places.
  • Mount Ascutney State Park, Windsor: Gorgeous mountain vistas, unique hiking trails, and a beautiful family-friendly campground – Mount Ascutney State Park is a playground for nature lovers, history buffs, and outdoor adventurers. You can hike one of four trails to the summit or drive to the summit and hike the network of trails at the top.
  • Path of Life Sculpture Garden, Windsor: This 14-acre sculpture park is located in Artisans Park in Windsor, Vermont. Meander the paths through the garden and then relax with a beer at Harpoon Brewery.
  • Cornish-Windsor Covered Bridge, Windsor: This is the longest wooden covered bridge in the United States and the longest two-span covered bridge in the world.
  • King Arthur Baking Company, Norwich: King Arthur Baking Company got its start more than 200 years ago as the first flour company in the United States. You can visit King Arthur’s flagship store in Norwich, Vermont. Stock up on baking supplies, have a fantastic lunch, and sign up for a class at the King Arthur Baking School.
  • Dog Mountain, St. Johnsbury: Dog Mountain is set on 150 acres on a private mountaintop in St. Johnsbury, Vermont. The grounds are always open to people and their dogs. Be sure to visit the Dog Chapel, where people from all over the world come to pay tribute to dogs they have loved and lost.

Where to Stay on the Connecticut River Scenic Byway

Read Next: Paddle the Connecticut River in Windsor, Vermont

Crossroads of Vermont Byway: Rutland to Quechee

1-2 days, 41 miles

The Middle Covered Bridge in Woodstock, Vermont.
A covered bridge in Woodstock, Vermont in the fall

This 41-mile Vermont road trip travels from east to west through the middle of the state, traversing the Green Mountains. It can be completed in a single day, or you can stretch it out and make a weekend of it.

Start your adventure in Rutland, which got its start as a working-class city and a leading producer of marble, but has quickly become a premier destination for art lovers.

As you head east, you’ll travel through the mountain towns of Mendon, Killington, and Bridgwater before descending into Woodstock and Quechee.

You can easily do this trip in a single day, spending the morning in Rutland and arriving in Woodstock in time for a late dinner. If you choose to spend the night in Woodstock, you should spend another full day there exploring and adventuring.

Eric standing at the top of Bucklin Trail in Killington, Vermontl.
View from the top of Killington Peak in Vermont.

Recommended stops on this Vermont road trip:

Where to Stay in Woodstock

We just couldn’t narrow it down, so here are a few choices!

Read Next: 10 Perfect Things to do in Woodstock in the Fall

Green Mountain Byway: Waterbury to Cambridge (loop)

2-3 days, 71 miles

Bingham Falls Vermont.
Bingham Falls in Stowe

This 71-mile scenic Vermont road trip is part of the larger Route 100 corridor, which in my opinion is one of the most scenic drives in New England.

The Northern Green Mountains are home to both jagged peaks and open farmland. Vermont’s highest peak, Mount Mansfield, as well as the stately Worcester Range, make this a dramatic landscape to explore.

The many historic towns that dot the landscape may seem isolated, but they have worked together to create communities that are as unique as they are welcoming to visitors.

The Green Mountain Byway starts in Waterbury and travels north through Stowe, Morrisville, Johnson, and Cambridge. You’ll drive through the famous Smuggler’s Notch, visit gorgeous waterfalls, and stop for a sampling of Vermont’s best ice cream, beer, cheese, and donuts. It’s quintessential Vermont in a weekend-long adventure!

While the Green Mountain Byway is a short loop, we recommend giving yourself a full weekend (or longer) to check out these sites:

Where to Stay in Stowe/Waterbury

Read Next: The Best Places to Visit in Vermont in the Fall

Lake Champlain Byway: Addison to Alburgh

2-3 days, 67 miles

The view from the top of Mt. Philo in Mt. Philo State Park in Vermont.
A view of Lake Champlain from the top of Mount Philo

In its entirety, the Lake Champlain Byway totals 185 miles, hugging the length of Lake Champlain all the way to the Canadian Border.

Traveling through fertile farmland with both the Adirondacks and the Green Mountains as a distant backdrop, this scenic Vermont drive has something for everyone, whether you want to get out on Vermont’s biggest lake, explore Vermont’s biggest city, or get lost on a back road.

Start in Vergennes, Vermont’s smallest city (by area), and drive north on picturesque Route 7 into the relative metropolis of Burlington for a day of shopping and culture, and a night on the town.

Finally, spend some time exploring the Lake Champlain Islands, including Vermont’s first commercial winery and an ancient coral reef.

The Round Barn at the Shelburne Museum.
The Round Barn at the Shelburne Museum.

We recommend taking two to three days to see the following sites on this beautiful Vermont road trip:

Where to Stay on the Lake Champlain Byway

Read Next: The Best Things to do in Burlington, Vermont this Summer

Mad River Byway: Warren, Waitsfield, and Middlesex

1 day, 36 miles

Route 100 in Warren, Vermont
Driving the back roads

The Mad River Byway is another short Vermont road trip that covers a small section of Route 100 and 100B, from Warren to Middlesex. If you have a few extra days, you should add this section to the Green Mountain Byway or Scenic Route 100 Byway.

If you are looking for a fantastic day trip, the Mad River Byway is ideal. We recommend doing it in the summer, so you can take advantage of all the swimming holes and hiking in the area, but the leaf-peeping is spectacular here too.

Here are some of our favorite stops on this Vermont road trip:

  • Warren Falls, Warren: One of the best swimming holes in Vermont, Warren Falls is located right off Route 100. There are shallow spots for kiddos, deep spots for cliff jumping, and gorgeous waterfalls to check out when the water is too cold to swim.
  • Mad River Taste Place, Waitsfield: A specialty grocery store with delightful Vermont products, including cheese, meats, maple syrup, and gourmet foods. It’s a great stop for road trip picnic supplies and gifts!
  • Mad River Path: Mad River Path is an organization dedicated to creating a system of continuous public pathways and trails connecting Warren, Waitsfield, Fayston, and Moretown. Choose from numerous trails of varying levels of difficulty.
  • Red Hen Baking, Middlesex: This is our favorite bread in the state, and we have been known to embark on long car rides to get our hands on it. Since you’re in the area, you have to stop for lunch and an extra loaf for the journey!

Where to Stay on the Mad River Byway

Moose Meadow Treehouse in Waterbury, Vermont.
Moose Meadow Treehouse

Seeing as this is a short road trip, you probably won’t require an overnight in the area. If you are planning for a special occasion, though, I do have to mention this luxurious treehouse rental near Waterbury at the northern end of the Mad River Byway and the southern end of the Green Mountain Byway.

We stayed at Moose Meadow Treehouse for our anniversary a few years ago and loved every minute of it. Moose Meadow Lodge also offers more traditional lodging. Visitors have access to a hot tub, a delightful breakfast, and hiking trails.

Molly Stark Byway: Bennington to Brattleboro

3 days, 48 miles

Dot's Diner in Wilmington, Vermont.

The Molly Stark Byway is another short road trip that you can easily do over a long weekend. It begins in Bennington and travels through the Green Mountains on Route 9 through Woodford (the highest village in Vermont at 2,215 feet), Wilmington, ending in Brattleboro.

In case you are curious about Molly Stark – she was the wife of General John Stark, who led a Colonial militia to victory at the Battle of Bennington in 1777.

The region provides the perfect mix of history, art, and outdoor recreation, and we recommend giving yourself three days to explore the following sites:

Where to Stay on the Molly Stark Byway

Northeast Kingdom Byway: St. Johnsbury to Newport

2 days, 51 miles

A view from the visitor center at Silvio O. Conte National Wildlife Refuge in Vermont.

The Northeast Kingdom is one of the wildest places in Vermont and has some of the most beautiful landscapes in the country.

Featuring lush, impenetrable forests, hidden lakes, and enduring farmsteads, the Northeast Kingdom is special. You do have to look beyond the lousy cell service and unpredictable weather, but what you’ll discover is a little piece of paradise.

The Northeast Kingdom Byway covers 51 miles between St. Johnsbury and Newport, as well as the small towns of Lyndon, East and West Burke, Westmore, Charleston, and Derby. This Vermont road trip is for nature lovers – be on the lookout for moose and deer as you drive – slowly.

Give yourself two days to explore the Northeast Kingdom.

Here are the must-visit sites and attractions on this special Vermont road trip:

Where to Stay on the Northeast Kingdom Byway

There are few hotels in the area, but plenty of campgrounds and cottages for rent. Check out Mountain Lake Cottages on the shore of Lake Willoughby to unplug and relax while exploring the Northeast Kingdom.

Scenic Route 100 Byway: Wilmington to Granville

2-3 days, 103 miles

Vermont Route 100 in the fall.
Scenic Route 100 in Vermont

If you can only choose one road trip through Vermont during your vacation, drive Route 100 from Wilmington north to Granville. Yankee Magazine called this route the best foliage drive in New England, and we couldn’t agree more.

Start in Wilmington (mentioned in the Molly Stark Byway) and head north on a leisurely journey through the mountains. Two days should be sufficient, but take three if you want to explore more of the trails and natural areas.

The northern end of the Scenic Route 100 Byway connects with the Mad River Byway in Warren.

Here are the stops you won’t want to miss on this spectacular Vermont road trip:

  • Mount Snow, West Dover: In the summer and fall, you can take the Bluebird Express gondola to the top of the mountain. In the winter, Mount Snow is a popular ski resort.
  • Jamaica State Park, Jamaica: Swim in the river, ride your bike on the West River Rail Trail, and hike to Hamilton Falls.
  • Vermont Country Store, Weston: Vermont’s most iconic country store. Come sample Vermont cheeses, buy some penny candy, and outfit yourself in Vermont flannel!
  • Buttermilk Falls, Ludlow: Located in Okemo State Forest, this lovely waterfall is also a popular spot for swimming in the summer.
  • President Calvin Coolidge Historic Site: Explore the birthplace and childhood home of our 30th president. The historic village appears much as it was during Coolidge’s lifetime.
  • Hike Killington: There are numerous trails in the Killington area. Here are our favorite day hikes, from easy to strenuous.
  • Moss Glen Falls, Granville: One of Vermont’s prettiest waterfalls is right off Route 100.

We cover the whole 217 miles of Route 100 in our 5-day fall-foliage itinerary.

Where to Stay on the Scenic Route 100 Byway

Read Next: The Best Things to Do in Wilmington, Vermont

Shires of Vermont Byway

2 days, 23 miles

two cows grazing in a field in Sunderland, Vermont.
Randall cattle enjoying fall foliage in Sunderland, Vermont

Welcome to my home turf! The Shires of Vermont Byway is named for the scenic region it passes through in southwestern Vermont.

This pastoral road trip takes through a narrow valley between the Taconic Mountains to the west and the Green Mountains to the east.

Start your journey in Bennington, which is also the start of the Molly Stark Bway mentioned above. Drive north on Route 7A through historic towns and farms. Dirt and gravel side roads will undoubtedly tempt you, so be sure to give in a few times.

You never know what you’ll see on the back roads of southwestern Vermont!

Spend a night in Bennington and a night in Manchester to discover this 23-mile road trip.

Here are a few spots you won’t want to miss on the Shires of Vermont Byway:

  • Old Bennington: Take a self-guided walking tour to explore the Bennington Monument, Old First Church, and the Bennington Museum, as well as numerous historic homes.
  • Covered Bridges of Bennington County: Before leaving Bennington, check out three covered bridges. Two more can be seen in Arlington, farther north.
  • Lake Shaftsbury State Park, Shaftsbury: This is a small park with a lake for swimming and a one-mile trail around the lake.
  • Hildene, Manchester: This was the former summer estate of Robert Todd Lincoln, son of President Abraham Lincoln. The grounds of Hildene are worth a visit, and you can also take a tour of the house, visit a restored Pullman Car, walk the trails, and tour the working farm.
  • Southern Vermont Arts Center, Manchester: Home of the largest outdoor sculpture park in Vermont, as well as large indoor galleries with rotating exhibits.

Where to Stay on the Shires of Vermont Byway

  • The Harwood Hill, Bennington: An eclectic, artsy motel next door to a restaurant.
  • The Barnstead Inn, Manchester: Modern rooms and suites on beautiful grounds within walking distance to the downtown area.

Stone Valley Byway: Manchester to Hubbardton

2 days, 43 miles

The Gettysburg Quarry in Dorset, Vermont.
The Gettysburg Quarry in Dorset, Vermont

Starting in Manchester, where the Shires of Vermont Scenic Byway leaves off, hop on the Stone Valley Byway, where you will learn about America’s most noted marble and slate quarries on your way to the historic town of Hubbardton.

Some of the abandoned quarries, like the Dorset Quarry, have been repurposed into popular swimming holes. Others, like the Gettysburg Quarry (pictured above), are abandoned and can be accessed via hiking trails.

Winding through fertile farmland along Route 30 for 43 miles, this is one of the loveliest Vermont scenic drives, and it makes a perfect weekend adventure. This is also a spectacular bicycle route for those of you who enjoy traveling best on two wheels.

Here are the sites you won’t want to miss on the Stone Valley Byway:

  • American Museum of Fly Fishing, Manchester: The Battenkill River, which flows through this region, is a world-class fly-fishing river, so it’s only fitting that Manchester is the home to the American Museum of Fly Fishing.
  • Dorset Quarry, Dorset: If you’re driving Route 30 in the summer, you’ll find the Dorset Quarry hard to resist. Stop for a dip before continuing on your journey.
  • Gilbert’s Lookout Hike, Dorset: The Town of Dorset maintains a fabulous network of hikes in the Dorset Town Forest. Our favorite is the hike to Gilbert’s Lookout, which features far-reaching views and several abandoned marble quarries.
  • Lake St. Catherine State Park, Poultney: Rent a kayak or canoe, hike the short nature trail, or take a dip in the beautiful waters of Lake St. Catherine.
  • Hubbardton Battlefield State Historic Site, Hubbardton: Site of the only Revolutionary War battle fought on Vermont soil. The Battle of Hubbardton took place on July 7, 1777.
  • Taconic Mountains Ramble State Park, Hubbardton: This day-use park features hiking trails through meadows and forests, a Japanese Garden for your road trip picnic, and lots of songbirds. The mountain views are stunning!

Where to Stay on the Stone Valley Byway

For more information about these Vermont scenic drives, as well as a downloadable map and brochure, visit Vermont Vacation.

Which one of these incredible Vermont scenic drives do you want to explore first? Leave a comment and let us know!

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A collage of photos featuring Vermont scenic byways. Text overlay: 10 Scenic Byways in Vermont for your Next Road Trip.

Tara Schatz is a freelance writer and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers, an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, released in May 2023, and the author of 100+ Wonderful Ways to Experience Vermont.