Vermont Fall Foliage Road Trip: Scenic Drives & Hidden Gems

Thinking about a Vermont fall foliage road trip? You should be. This is one of the most magical places in the U.S. to see Fall at its peak.

I spent several days driving through Vermont during peak foliage season, from the top of the state all the way to the bottom. It was part of my bigger New England fall road trip through all six states. But out of them all, Vermont was my favorite by far.

The covered bridges, rolling hills, farm stands, and back roads bursting with color completely blew me away. I found so many hidden spots and small towns that I never wanted to leave. And I’m here to help you do the same.

In this post, I’ll show you exactly how to plan your own 3-day Vermont fall road trip. You’ll get the best places to visit, where to stay, and what to pack. Plus all the little tips I learned from doing this road trip myself.

A charming covered bridge in Woodstock, Vermont sits beside a pale yellow house with black shutters and a blooming pink hydrangea tree, surrounded by early autumn foliage. — Vermont was my favorite state in New England in the Fall!

Use My favorite Resources to Help Plan Your Vermont Trip

Best For Flights: Expedia
Best For Accommodations: Hotels.com
Best For Rental Car: Discover Cars
Best For Experiences: Viator

A scenic view along Vermont’s Highway 100 shows a peaceful farmstead nestled among rolling green fields and forested hills bursting with vibrant fall foliage. — Beautiful farms along scenic Highway 100

Best Places to Visit in Vermont in Fall

Vermont is full of charming towns and stunning landscapes, but some places stand out more than others in the fall. Here are the spots you won’t want to miss on your road trip.

Green Mountains – This mountain range runs through the heart of Vermont and puts on an incredible fall color show. The scenic views along the ridges and valleys are unreal.

Montgomery – Known as the covered bridge capital of Vermont, this tiny town is full of charm. It’s also the starting point of the most scenic route in Vermont. (see next)

Scenic Highway 100 – This route is often called the most beautiful drive in the state. It stretches from north to south and is packed with the best foliage, small towns, and roadside gems.

Stowe – A classic New England village with white churches, mountain views, and fun things to do. It’s also one of the most popular fall destinations in Vermont.

Woodstock – This town looks like it was made for a fall postcard. Think red barns, rolling hills, covered bridges, and a super cute downtown.

Map of This Vermont Fall Road Trip

Your Perfect 3 Day Vermont Fall Foliage Road Trip

This Vermont fall foliage road trip was part of my two-week New England adventure through all six states. We drove into Vermont from New Hampshire after cruising the stunning Kancamagus Highway—another epic fall route you should definitely add to your list. From there, we picked up scenic Route 100 at the top of the state and followed it all the way down toward Connecticut.

Vermont completely stole the show. We spent three full days exploring and honestly, it wasn’t enough. We could’ve stayed for a week.

If you want the best of Vermont crammed in just a few days, this itinerary will help you make the most of your time.

Let’s hit the road!

Kate standing by the Longley Covered Bridge in Montgomery, Vermont, during peak fall foliage season. — Montgomery, Vermont – the covered bridge capital

Day 1: Montgomery, VT + Drive Highway 100

Today kicks off your road trip with one of the prettiest drives in all of New England.

Start in Montgomery, explore some iconic covered bridges, and then make your way south along scenic Highway 100 toward Stowe. Take your time and enjoy every stop—the journey is just as good as the destination.

Montgomery, VT

Why start in Montgomery?

Because it’s the covered bridge capital of Vermont! At one time, this little town had thirteen bridges. Today, seven still remain, and each one is more charming than the last.

As you drive through Montgomery and its backroads, you’ll pass through hills blanketed in red, gold, and orange leaves. It’s honestly some of the most beautiful countryside I’ve ever seen.

Plus, this town marks the start of Highway 100, a road that’s famous for its fall foliage and one of the most popular scenic drives in the state.

A rustic wooden covered bridge in Vermont is lit by golden late-afternoon sunlight, casting long shadows across the gravel path. — Exploring Vermonts backroads

Two beers from von Trapp Brewing—a golden lager and a dark stout—sit on a wooden bar, with their logos clearly visible in a cozy Vermont taproom. — Von Trapp Brewing Bierhall – a taste of Austria

Drive Highway 100 to Stowe, Vermont

After exploring Montgomery and her covered bridges, grab a coffee to go (and maybe a delicious slice of pizza from the pub) and head south along Highway 100. I highly recommend taking the backroads as often as possible. This is where the magic happens.

The drive to Stowe only takes 50 minutes without stops, but trust me, you’ll want to take your time.

You’ll pass through quiet villages, open farmland, and those iconic sugar maples lining the road. This stretch is full of hidden gems, and it truly feels like you’re driving through a live postcard.

The white Hutchins Covered Bridge in Vermont stands framed by vibrant fall foliage in shades of yellow, orange, and red, capturing a classic New England autumn scene. — Hutchins Covered Bridge

Places to visit along the way to Stowe:

Covered Bridges – You’ll pass a few more as you go, including the Hutchins Covered Bridge in Montgomery and Grist Mill Covered Bridge in Jeffersonville.
Smugglers’ Notch State Park – This spot is worth a short detour for its dramatic cliffs, winding road, and colorful hiking trails.
Mount Mansfield Gondola – Take a ride to the top of Vermont’s tallest peak for a view you won’t forget.
Von Trapp Brewing Bierhall – Head up the mountain for craft beer, Austrian eats, and incredible views. We had schnitzel here for the first time—and wow. So good.

Kate stands by a crackling campfire in the woods, holding a bottle of beer and dressed warmly in overalls, boots, and a long cardigan on a crisp autumn evening. — We chose to camp just outside Stowe.

A quiet dirt path winds through a golden forest in Vermont, with fallen leaves blanketing the trail under a bright blue sky.

Where to Stay in Stowe

About 40 minutes outside of Stowe, we found a quiet stretch of national forest where we wild camped for the night. It was totally free, felt safe, and the setting was beautiful. We grabbed a bundle of firewood in Waitsfield, built a cozy fire, and watched the stars come out—pure fall magic.

But if camping isn’t your thing, I highly recommend checking out the Green Mountain Inn. It’s right in the heart of downtown Stowe and full of charm, with cozy rooms, fireplaces, and easy access to shops and restaurants. After a day of exploring, it’s the perfect place to relax and warm up.

An aerial view of Stowe, Vermont at sunset shows the town nestled among rolling hills and autumn foliage, with a white church steeple rising at the center and a winding river reflecting golden light. — Stowe, Vermont

Day 2: Explore Stowe & Woodstock, VT

Today is all about soaking up small-town charm, beautiful scenery, and yummy fall treats. All the Vermont goodness!

Start your morning exploring the picture-perfect village of Stowe, then continue your drive south on Highway 100 toward Woodstock.

Explore the Quaint Town of Stowe

Stowe literally feels like it’s straight out of a Hallmark movie.

Surrounded by glowing mountains and full of charm, it’s no wonder why it’s one of Vermont’s most popular fall destinations. With white steepled churches, sugar shaks, and friendly locals, it’s a great place to spend a crisp fall morning.

Kate poses smiling in front of a rustic “Stowe Maple Products” sign surrounded by pumpkins and hay bales, celebrating Vermont’s maple season. — Stop at roadside sugar shacks!

The entrance to Cold Hollow Cider Mill in Vermont is decorated with bright mums and pumpkins, welcoming visitors with signs for free samples and specialty foods. — Cold Hollow Cider Mill has the best cider donuts!

Best things to do in and around Stowe:

Wander the Main Street shops – Don’t miss Stowe Mercantile. It’s packed with old-school candy and local gifts.
Walk or bike the Recreation Path – This 5.3-mile path winds along the river and through open fields, starting behind the Stowe Community Church.
Snap a photo of the white church – It’s the most photographed church in the U.S. and a true New England icon.
Stop at roadside sugar shacks – Try maple syrup in every form: candy, butter, and warm right out of the tap.
Cold Hollow Cider Mill – Grab a hot cider, a fresh donut (or a dozen), and check out their seasonal hard cider bar. So good!
Ben & Jerry’s Factory – Head over to nearby Waterbury to tour the famous factory and try fun seasonal ice cream flavors you can’t find anywhere else.

The Woodstock Middle Bridge in Vermont stands wet from rain, framed by golden autumn leaves and a sign that reads “Slippery When Wet,” capturing the charm of a classic New England fall day. — The iconic Woodstock Middle Bridge

Drive to Woodstock

Next, hop back on scenic Highway 100 and make your way down to Woodstock. The drive takes about 1 hour and 20 minutes without stops, but we just know that it’s going to take longer, so give yourself plenty of time.

Along the way, you’ll pass pumpkin patches, more cute sugar shacks, roadside farm stands, and orchards framed by rolling hills covered in peak fall color. You’ll want to pull over every five minutes.

Kate pulls a red wagon through a sunny Vermont pumpkin patch, surrounded by neatly arranged rows of pumpkins and a hillside sign that reads “VERMONT.”

Wooden crates display fresh Vermont apples—Galas, Honey Crisp, and Zestars—each labeled with handwritten pricing on chalkboard signs.

Places to stop along the way to Woodstock:

Farm stands – You’ll see little shacks selling fresh seasonal produce, maple products, and handmade jams. Most of them run on the honor system, which I just loved.
Pumpkin patches – Even if you can’t take one with you, it’s still fun to stop and walk through. So many perfect photo ops!
Apple orchards – Pick a few apples for the drive or grab a cider slushie if they have one.
Covered bridges – Because Vermont can’t stop, won’t stop with the covered bridge cuteness.

A stately red brick home in Woodstock, Vermont features black shutters, window boxes, and small pumpkins lining a white picket fence, all framed by autumn foliage and an American flag.

A large red maple leaf-shaped sign welcomes visitors to Sugarbush Farm in Vermont, with weathered wooden arrows pointing to the Maple Walk, Sugar House, and Maple Displays.

Explore The Charming Town of Woodstock

As soon as you pull into Woodstock, it feels like you’ve stepped onto the set of Gilmore Girls.

The town is full of old brick buildings, covered bridges, white churches, and family-run shops. It’s surrounded by farmland and trees that explode with color in the fall—it’s seriously picture-perfect.

The classic weathered barn of Sleepy Hollow Farm with a tin roof sits among vibrant fall foliage in rural Vermont, surrounded by rolling fields and a winding gravel path. — Sleepy Hollow Farm

Best things to do in Woodstock:

Snap a photo of Sleepy Hollow Farm – One of the most iconic fall views in all of Vermont.
Tour Sugarbush Farm – Sample every kind of cheese you can imagine and maple syrup, and soak in some pretty amazing foliage views while you’re there.
Take a scenic drive down Cloudland Road – It’s peaceful, scenic, and very Vermont.
Hike in Marsh-Billings-Rockefeller Park – There’s a trail that leads to a great overlook of Woodstock.
Stop by Billings Farm & Museum – It’s a working dairy farm where you can meet the cows and learn about local farm life.
Explore the historic covered bridges – Don’t miss Middle Bridge and Taftsville Covered Bridge.
Wander downtown – The boutiques, cafés, and local galleries are full of charm.
Eat at Worthy Kitchen – We had an incredible dinner here. Farm-to-table, fresh, and so good after a full day of exploring.
Visit Quechee Gorge – Called Vermont’s “Little Grand Canyon,” this dramatic river gorge is perfect for a quick walk and photo stop.
Pop into Quechee Village – Just down the road, it’s another cute stop with shops and views.

Where to Stay in Woodstock

We didn’t actually stay overnight in Woodstock. We drove a little farther to the town of Lebanon, right on the Vermont/New Hampshire border. After a couple of days camping, we were ready for a hot shower and a real bed!

Lebanon had more budget-friendly hotel options, plus a grocery store to restock supplies. It also put us super close to the Cornish-Windsor Covered Bridge, which was on our list for the next morning.

But if you do want to stay right in Woodstock (and honestly, it’s hard to resist), I highly recommend On The River Inn. It’s modern, cozy, and sits right along the river with beautiful views. The rooms are super comfy, and the outdoor fire pits and charming decor make it the perfect place to wind down after a day of exploring.

Day 3: Explore more of Woodstock + Windsor Bridge + Drive to The Berkshires

It’s the final day of your Vermont adventure!

Spend the morning soaking up more of Woodstock if you chose to spend the night here, then swing by one of the most famous covered bridges in the country before hitting the road. If you have time to keep going, the Berkshires make the perfect next stop for even more fall beauty.

Explore More of Woodstock

If there’s anything you didn’t get to see yesterday, this is your chance to check it off. Whether it’s another maple tasting, one last scenic hike, or just grabbing a slow breakfast at a local café, I recommend slow rolling out of Woodstock and soaking it in as much as you can.

The Cornish-Windsor Covered Bridge stretches across the Connecticut River under a bright blue sky, its weathered wooden exterior and white entrance blending into the fall landscape between Vermont and New Hampshire. — Cornish-Windsor Covered Bridge – longest covered bridge in the US

Windsor Bridge

Before leaving the area, make a short detour to see the Cornish-Windsor Covered Bridge. It connects Vermont to New Hampshire and is the longest covered wooden bridge in the U.S.—and the longest two-span covered bridge in the world. It’s a quick stop, but totally worth it for the photos and the fun history.

The bright red Tannery Bridge in Vermont stands out against a backdrop of colorful fall foliage, with golden trees framing its rustic wooden structure under a clear blue sky. — The Tannery Bridge

Drive to the Berkshires or End Your Road Trip

If you’re continuing your New England journey, head south into The Berkshires in western Massachusetts. This area has some of the most stunning fall foliage in the entire state with rolling hills, fiery forests, rustic cabins, and artsy little towns.

From Woodstock, the drive takes about 2 hours without stops. But don’t miss a quick pit stop in Rockingham, VT to visit the Vermont Country Store (it’s like stepping back in time!) and snap a photo at the Kissing Covered Bridge before you cross the border.

Head Home

Congratulations—you made it all the way through my favorite New England state in the fall! I hope Vermont wowed you as much as it did me, with all its colorful roads, cozy towns, and unforgettable views.

If this is the end of your road trip, start making your way to the airport you’re flying out of. Whether that’s Boston, Albany, or Burlington, just be sure to leave yourself plenty of time for the drive (and maybe one last cider donut stop on the way!).

A vibrant maple tree glows with fiery red, orange, and yellow leaves as sunlight filters through its branches on a crisp Vermont autumn day.

A winding two-lane road curves through a vibrant autumn forest in Vermont, with golden, orange, and red foliage lining both sides under a soft blue sky.

Best Time to Visit Vermont For Fall Colors

Peak foliage usually happens between late September and mid-October, but it can shift depending on the weather that year. I always recommend checking a fall foliage tracker or “leaf forecaster” map before your trip so you can catch the colors at their best. Just keep in mind that Mother Nature has her own schedule, so flexibility is key!

If you want a deeper breakdown of the best dates, tips, and how to plan around the changing leaves, I’ve got a full post on the best time for fall colors in New England that’ll really help.

How to Get to Vermont

You’ve got a few good airport options when flying into Vermont. Burlington is the closest if you want to fly right into the state. But you can also fly into Boston, Albany, or even Hartford—they’re all just a few hours’ drive away and often have better flight deals.

We flew into Boston Logan Airport because it had nonstop flights, good prices, and easy access to the rest of New England. One of the best parts about this region is how compact it is. Once you land, it’s super easy to drive from state to state and make the most of your trip.

And while we were there, we spent a weekend exploring the city before hitting the road.

If Boston’s on your radar too, check out my post on whether it’s worth visiting and what not to miss.

How Best to Get Around Vermont to See The Colors

This gorgeous state is full of hidden gems and small towns that are best explored at your own pace. So you really need your own wheels.

If you want to see Vermont properly in the fall, renting a car is a must. Having your own vehicle gives you the flexibility to stop at every cute general store, covered bridge, or random roadside farm stand that pops up. Trust me, the ability to pull over when the light hits the trees just right is worth it.

Book with Discover Cars for the best rates!

Kate takes a cozy selfie in a rain jacket with a hood up, standing in front of a covered bridge surrounded by golden autumn trees in Vermont. — A raincoat is a must!

Kate smiles excitedly while holding a striped mini pumpkin at a roadside farm stand lined with colorful gourds and bright fall sunshine.

What to Pack For Your Vermont Fall Road Trip

Fall weather in Vermont can be unpredictable, so layering is key.

Pack a warm, waterproof coat, a cozy hat and gloves (especially if you’re heading into the mountains), and comfortable fall boots for exploring trails, farms, and scenic overlooks.

And if you want more packing tips, check out my full Fall Packing Guide here.

Also here a few things that almost no one tells you to bring:

Collapsible travel mug – Perfect for filling up on hot cider or coffee at roadside stops without wasting cups.
Rechargeable hand warmers – Total game-changer for chilly mornings and long photo stops.
Roll Top Dry Bag Backpack – It rains more than you’d think in the fall, and this keeps your gear totally dry on hikes.
Mini Tripod + Bluetooth Remote – For getting the perfect shot when no one else is around. I never travel without mine.
Blow Up Travel Lumbar Pillow – OMG, this is a lifesaver on long road trips. I can’t even explain how much it helps. Just trust me.

That’s a Wrap

I hope this guide helps you plan the Vermont Fall Foliage Road Trip of your dreams! From covered bridges to cider mills, It was my favorite stop on our New England adventure, and I know it’ll be one of yours too.

Before you go don’t forget to grab your free printable New England Fall Road Trip Itinerary that covers all six states—I’ve done the legwork so you don’t have to.

And If you’re looking to add more stops or squeeze in a few extra fall favorites, I rounded up 21 must-do things across New England to give you even more inspiration.

Catch ya on the next adventure!