21 Bucket List Things To Do In Vermont In The Fall

There are so many amazing things to do in Vermont in the fall—from scenic drives and covered bridges to cider donuts and small towns that are too cute to be real. 

I spent 3 unforgettable days road-tripping through Vermont during my two-week fall road trip across all six New England states, and Vermont ended up being my absolute favorite. 

During my trip, I explored picture-perfect towns, sipped fresh apple cider, and got lost on quiet back roads lined with fall colors.

I’ll be sharing the very best fall activities and hidden gems I found, from hiking in the Green Mountains to visiting cute farm stands and historic spots. If you’re hoping to experience the best of Vermont in the fall, you’re in the right place.

By the end of this post, you’ll fall head over heels in love with Vermont!

When To Visit Vermont For Peak Fall Foliage

The best time to visit for peak colors is usually anywhere within the last week of September through mid-October. This is when the trees have not shed their leaves and the colors are brightest, especially in the northern and higher elevation areas. 

Keep in mind that Vermont’s colors change a bit earlier than other parts of New England due to its mountains and cooler temperatures. If you arrive too early in September, the leaves might still be mostly green—especially in the southern parts of the state. And if you wait too long after mid-October, most of the trees will have already shed their leaves.

For the best leaf peeping experience, try to time your trip around the first or second week of October. That’s when I saw the most stunning colors on my road trip. And don’t forget that colors can vary from year to year, so it’s always good to check local foliage reports before you go.

21 Bucket List Things To Do In Vermont In The Fall

There’s so many unforgettable things to see and do in Vermont that belong on your fall bucket list. 

From scenic drives, crisp mountain air, delicious farm fresh food, and charming small towns, Vermont is everything you’d hope for—and more. 

Here are 21 must-do activities that will help you soak up every moment of this beautiful time of year.

Drive Route 100

Route 100 is one of the most scenic drives in Vermont, winding through the Green Mountains and showcasing spectacular Vermont fall foliage at every turn.

From farms to forests, the colorful display of reds, oranges, and yellows creates postcard-perfect stops.
We started our exploring early in the morning to catch the soft light on quiet country roads, avoiding crowds and getting unobstructed views of rolling hills. It’s totally worth the early wake up call – trust me!

Pro Tip! the drive is so much better with this self-guided audio Tour. We had it playing as we drove and it made the drive so much more interesting! Highly recommend it!

Tour As Many Covered Bridges As You Can

Vermont is dotted with over 100 of the most charming covered bridges that are picture perfect and worth every detour.

I’m a bit obsessed with covered bridges, not going to lie. These wooden beauties aren’t just pretty, they’re part of New England’s history and charm and I must have hunted down at least two dozen on my Vermont Fall Road Trip.

Pro Tip: Head to Montgomery which is known as the Covered Bridge Capital. Once home to 13 covered bridges, the town still has six within its borders and one more nearby. Mongomery is also the start of the famous scenic Highway 100.

Make Sure You See The World’s Largest Covered Bridge

Just on the border of Vermont and New Hampshire is the Cornish–Windsor Bridge. 

This spansive beauty is said to be the longest covered wooden bridge in the world and is over 158 years old. It crosses the Connecticut River between Cornish, New Hampshire and Windsor, Vermont. 

It’s a very pretty bridge with a small parking area so you can get out and snap some photos of her. Definitely add her to your list!

Take The Back Roads

Some of Vermont’s best scenes are found off the beaten path, on her winding back roads. Plus you’ll have the added bonus of not having to deal with the hassle of heavy traffic.

During my three-day trip, spontaneous turns led to some of my favorite finds.  Maple stands, small farms, and perfect roadside photo ops framed by towering mountains and fall colors. 

If there is only one piece of advice you take from this post, make it to get off the beaten path and take the back roads. Trust me!

Find The Perfect Pumpkin at a U-Pick Pumpkin Patch

Visiting a U‑pick pumpkin patch is such a classic and joyful autumn experience for all ages. I rolled through fields of orange searching for the perfect pumpkin and felt like a kid again. 

My favorite and the most picturesque Pumpkin farm was the Armstrong Farm in Bennington. It may be small, but it makes up for it in charm. Be sure you hit up this one!

Visit The Cute Self-Serve Farm Stands

Scattered along Vermont’s Route 100 you’ll find several self-serve farm stands that are super charming and convenient for fresh produce and local goods.

I filled my bag with crisp apples, bright squash, and jams—then paid with cash in the honor-system box. I find it so nostalgic that these honor systems still exist! 

Be sure to have cash and small bills on hand if you plan on stopping at a few.

Explore The Cute Town Of Stowe

Stowe is a storybook town, especially in fall when the streets are framed by vibrant orange maple trees.

When you visit, walk or bike the Stowe Recreation Path, snap pictures of the classic white church on main street, browse the general store, and take the Stowe Gondola ride up Mount Mansfield for panoramic mountain views.

During our visit we only spent a few hours here and I wish so much that we didn’t have to keep moving and could have spent the night. It’s such a gorgeous little town and deserves more time than we had to give.

Drive Through Smugglers Notch State Park

Smugglers Notch is a dramatic mountain pass carved through the green mountains, offering unbeatable fall scenery.

The winding road passes sheer rock walls and overlooks filled with vibrant fall colors that were both magical and jaw dropping at the same time.

And If you’ve got more time, some of the best hiking trails are in this state park!

Take A Fall Foliage Hike

Vermont’s Green Mountains have the best Hiking trails in the state. Especially during the fall season they are even more spectacular. 

If you’re looking for that one trail to do while you’re there hiking to the top of Mount Mansfield is a must. You’ll be rewarded with sweeping mountain views and the crisp scent of autumn.

Visit Cold Hollow Cider Mill

Cold Hollow Cider Mill is a fall favorite with freshly pressed apple cider and the most yummy cider donuts.

I grabbed a steaming cup by the window and soaked in the warm, cinnamon-kissed aroma while I devouerd not one but two apple cider donuts. 

And if hot cider isn’t your thing, sample their hard ciders. We got a flight of all their flavors. They were all so good it was hard to pick a favorite. 

Search For The Best Cider Donuts

Cider donuts are a fall staple in Vermont, and finding the best is a delicious quest.

I sampled warm, cake-style donuts from various orchards and farmers’ markets—each were delicious but I’ll still stick with the best being from Cold Hollow Cider Mill

Try All the Seasonal Brews And Hard Ciders

Fall brings a wave of pumpkin ales, spiced beers, and crisp hard ciders that Vermont breweries and cideries brew just for the season.

We hopped between local spots, sampling flights of autumn-inspired drinks. I do have to say that pumpkin beer is my favorite seasonal drink, and Von Trapp Brewing Bierhall was my favorite brewery!. 

Visit Sugar Shacks And Sample Maple Syrup Goodies

A visit to a sugar shack in Vermont is an absolute must. They are known for them, and you will find them all along the scenic Highway 100. Just stop at whichever one catches your eye because they are all so cute.

We enjoyed maple just about every way you can imagine. From glazed pastries, maple cream, candies, and even maple-flavored ice cream.

Explore Manchester

Manchester combines historic charm with autumn elegance, nestled in rolling, colorful hills.

I wandered its quaint downtown, peeked into boutique shops, and relaxed with a coffee at a café. Then, we headed to see the famous Lincoln Family Home, which is now a historical museum. 

Go Apple Picking

Apple picking season in Vermont coincides with the peak fall season, so it’s the perfect fall activity to add to your list. 

Vermont’s apple orchards are quite picturesque and colorful in the fall.

We spent a few hours wandering the orchards, picking crisp apples and trying homemade apple goodies. The two orchards we really enjoyed were Boyd Family Farm and Southern Vermont Orchards below Manchester VT. 

Find Your Way Through The Largest Corn Maze

You have to visit the largest corn maze in New England which just so happens to be in Danville, Vermont. 

With two mazes, over 24 acres of pathways, towering walls of corn, 100 feet of bridges, an underground tunnel, and panoramic views it’s no wonder it’s been voted in the top 10 mazes in America every year. 

It’s so much fun and quite the challenge! Expect that it’ll take you about 2-3 hours to find your way through. And if you’re worried about getting lost and panicking don’t worry there’s emergency exits.

Open August 1st through Mid October. 

Explore The Charming Town of Woodstock

Woodstock feels like stepping straight onto the set of Gilmore Girls. It’s full of historic brick buildings and timeless charm, especially in the glow of fall.

We spent our day visiting the two beautiful covered bridges, white steepled church and a few cozy cafes and boutique shops in the downtown area. 

Visit Sugarbush Farm

At Sugarbush Farm, you can enjoy artisanal cheeses paired with local maple syrup—an absolutely delicious fall duo.

I tasted several samples and the aged cheddar and creamy gouda, with just a drizzle of maple, was my favorite!

Be sure to wander through or take a tour of the maple trees and taste maple syrup straight from the tree. 

Photograph the Famous Sleepy Hollow Farm

Sleepy Hollow Farm is a photographer’s fall dream, This iconic red barn set against brilliant foliage is probably one of the most instagram worthy and photographed spots in all of Vermont.

Arrive early for the soft morning glow and no visitors for unforgettable shots. 

Tour Billings Farm and Museum

You can’t really visit Woodstock and not visit the very popular Billings Farm and Museum just outside of town. 

It has a beautiful 1890 farmhouse and exhibits recreating 19th century farm life. You’ll also get to meet heritage breed cows, toured old barns, and watched farmers churn butter by hand.

Enjoy A hearty Meal at a Farm To Table Restaurant

One of the best ways to experience Vermont during the fall is through its food. And a farm-to-table meal is a must!

Vermont is quite known for its farm-to-table scene that uses only the best seasonal produce from local farms. Dining this way helps local growers. 

After a full day of leaf peeping and fun fall activities we cozied up with an incredible meal at Worthy Kitchen in Woodstock, where everything was fresh, local and so satisfying. 

Best Places to Visit In Vermont In The Fall

Vermont is full of breathtaking beauty, but a few places truly stood out as the best places to visit in the fall. These scenic spots showcase everything we love about a New England autumn.

If you’re short on time, these highlights are where you’ll want to focus your trip.

Green Mountains

The Green Mountains stretch the length of Vermont and are the heart of its fall magic.

In early to mid-October, the mountains light up with rich reds, oranges, and golds, especially at higher elevations.

I found some of the best hiking trails and overlooks here, with sweeping views of valleys blanketed in colors.

If you want the classic Vermont fall foliage experience, this region is a must.

Scenic Route 100

Route 100 is one of the most iconic drives in New England, and it’s easy to see why.

It winds through the center of Vermont, connecting charming towns, rolling hills, and dozens of leaf-filled photo ops.

I loved stopping at roadside farm stands and scenic overlooks along the way.

If you’re driving just one road in Vermont this fall, make it Route 100.

The Charming Towns of Stowe and Woodstock

Stowe and Woodstock are two of the most charming towns in all of Vermont and they shine brightest in the fall.

In Stowe, you can bike the recreation path, ride the gondola up Mount Mansfield, and wander through a town bursting with foliage.

Woodstock is known for its covered bridges, historic sites, and classic New England village green all surrounded by flaming trees.

Both towns are perfect if you want a mix of small-town charm and stunning fall views.

Smugglers Notch State Park

Smugglers Notch is one of the most dramatic and scenic spots in Vermont, especially during peak fall season.

Driving through the narrow mountain pass, you’re flanked by steep cliffs and bold color. It’s like driving through a canyon of leaves.

I stopped at several pull-offs to take in the views, hike short trails, and breathe in the crisp mountain air.

For nature lovers and photographers, Smugglers Notch is one of the best fall destinations in the state.

Best Places To Stay In Vermont In The Fall

Vermont has some of the coziest places to stay that feel like home. Plus, waking up in a historic town surrounded by rolling hills and fall colors right out your doorstep, it just can’t be beat. But the perfect stay can make it even more magical. 

So, here are the top spots in both Northern and Southern Vermont that I’d choose to stay in again. But book early and book fast because these spots fill up fast!

Northern Vermont

• Mad River Barn (Waitsfield) – This is such an adorable little Inn in the Mad River Valley. The property is gorgeous, and every room is super cozy. Perfect for a fall getaway.
• AWOL Stowe (Stowe) – A calm, adult-focused hotel dressed in Nordic-style design and in convenient proximity to Stowe’s village and recreation path. I’d choose one of the little cabins to stay in!
• On The River Inn (Woodstock) – This is such a cute and quaint little riverfront Inn with super comfy beds, a fantastic on-site restaurant, and a gorgeous bar and pool. And best of all, it’s in my favorite Town in Vermont. 

Southern Vermont

• The Manchester View (Manchester) – A charming, mountainside B&B offering fireplaces, spa tubs, and a heated outdoor pool—with sweeping valley views
• Reluctant Panther Inn & Restaurant (Manchester Village) – A boutique inn with museum-quality decor, fireplaces, and an award-winning restaurant—ideal for gourmet lovers and fall foodies
• Inn on Putney Road (Brattleboro) – A luxurious six-room estate with a romantic atmosphere, elegant gardens, and close proximity to artsy downtown Brattleboro

What To Wear In Vermont In the Fall

When you visit Vermont in the fall, layering is going to be key.

Mornings and evenings are often pretty chilly, while midday can be surprisingly warm. And I’d come prepared for rain also by throwing a packable umbrella and raincoat in your suitcase.

If you’re planning a fall getaway that includes outdoor adventures like hiking, bring a pair of sturdy shoes and accessories like a beanie and scarf. 

Must-Pack Items For Fall In Vermont

Here are the must-have essentials I think you’ll definitely want to pack with you!

Collapsible Travel Thermos

This collapsible travel thermos was perfect for keeping my hot cider or coffee warm while I was on the go. I’m so glad I brought it!

Cute & Comfy Waterproof Boots

Waterproof Boots are essential for muddy trails, rainy days, and farm visits. But I also understand the importance of them being cute, too. These Columbia boots are perfect! I love mine and have worn them on many off-season trips.

Wind Resistant Umbrella

A compact, wind-resistant umbrella is a must for those surprise fall showers and strong gusts. I had a cheap umbrella and it got demolished by the wind. So save yourself now and just get this super wind-resistant umbrella. 

Rain Jacket

A lightweight, waterproof jacket is key for unpredictable Vermont weather. Go for this one with a hood and soft liner to stay warm and dry on hikes or in town.

Travel Camera

With the fall colors at their peak, you’ll want to capture every golden hillside and covered bridge. Bring your best camera. 

This compact Fuji camera is my favorite travel camera! 

Insider Tips For Visiting Vermont In The Fall

Fall in Vermont is one of the busiest and most beautiful times of the year, and knowing a few key tips can definitely help you enjoy the experience without any stress.

Here’s what I learned from my own leaf-peeping adventure through the Green Mountain State.

Best Way To Get Around Vermont

To truly experience fall in Vermont, you’re going to need a car, no question.

Having a car gives you the freedom to pull over for photos, take back roads, and stop at small farm stands or maple syrup shacks. I found some of the most breathtaking views by following signs off the main highways that I wouldn’t have been able to reach without a car. 

PS. I always book my rental car with Discover Cars. I haven’t found a site I like better! They give you the exact price right up front with no hidden fees, and they have a great free cancellation policy, which we all know can be a lifesaver. 

How to Avoid The Crowds

If you want to skip most of the crowds, plan your trip for midweek rather than the weekend. 

Popular towns like Stowe and Woodstock can get very busy during peak foliage weekends, especially in early October. By arriving on a Tuesday or Wednesday, I found quieter trails, easier parking, and more relaxed visits to local attractions.

Plan Ahead

Fall is Vermont’s peak travel season, and things book up fast. I recommend reserving hotels, tours, and even gondola rides months and months in advance to avoid missing out. So, as soon as you know your dates, lock everything in ASAP! You might also get better rates. 

Take The Back Roads

One of the best ways to see Vermont’s fall colors is by taking the back roads. 

During our road trip, we stumbled across some of the most stunning covered bridges and peaceful valleys just by venturing off the main roads. The slower pace let us stop for photos whenever we wanted—and we often had the view all to ourselves. It was truly some of our most favorite memories of the whole trip

Be Respectful Of Private Property

When you’re chasing the perfect fall shot, it’s tempting to wander off the road or onto a pretty-looking property, but always respect signs and fences. 

Many farms and homes in Vermont are private, and walking onto someone’s land without permission isn’t just rude—it can be dangerous. Stick to public areas and scenic pull-offs for your photos.

FAQ’s About Visiting Vermont In The Fall

Here are some of the most common questions and answers, and just some quick tips I think will help you make the most of your visit.

Where is the best place in Vermont to visit in the fall?

Stowe, Woodstock, and Highway 100 are some of the best places to visit in Vermont in the fall. These areas offer the perfect mix of colorful foliage, scenic drives, charming small towns, and cozy spots to stay.

How long does peak foliage last in Vermont?

Peak foliage in Vermont typically lasts about two to three weeks, from the last week of September through mid-October. Timing can vary slightly depending on elevation and weather, so check local foliage reports before you go.

How many days are needed in Vermont?

I recommend spending at least 3 to 4 days in Vermont to get a good taste of the region. This gives you enough time to enjoy scenic drives, visit a few towns, and take in the fall colors at a relaxed pace.

What is the most scenic route in Vermont?

Route 100 is considered the most scenic route in Vermont, especially during fall. It winds through valleys and mountains, passing through charming towns, covered bridges, and plenty of photo-worthy stops.

Is Vermont or New Hampshire better for fall foliage?

Both states are stunning in the fall, but Vermont has more open farmland, charming villages, and iconic covered bridges. If you’re looking for classic New England charm with rolling hills and postcard-perfect scenery, Vermont is hard to beat.

That’s a Wrap on The Best Things To Do In Vermont In The Fall

That’s a wrap on the best things to do in Vermont in the fall—from scenic drives and hikes to cider donuts and charming towns.

If you’re planning a New England fall getaway, go ahead and steal my exact Itinerary or use it to help you plan yours! 

And before you go, download and print my free Fall New England Road Trip Itinerary, which covers all six states.