The Perfect 7-Day Vermont Fall Road Trip Itinerary

A Vermont fall road trip is hands down one of the best ways to experience New England’s foliage season! With its winding scenic roads, charming small towns, and fiery maple trees at every turn, Vermont in the fall feels like it was made for road tripping.

This 7-day Vermont fall road trip itinerary starts in Boston and ends in Stowe, taking you through some of the most beautiful spots in the state. You’ll explore covered bridges, hike to breathtaking viewpoints, sample fresh cider and maple syrup, and spend time in the kind of postcard-perfect villages that make Vermont famous.

It’s the perfect way to soak up Vermont’s fall colors at a relaxed pace, with plenty of time for scenic detours, cozy cafés, and spontaneous photo stops along the way.

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Good to Know Before Your Vermont Fall Road Trip

🍁 When is the best time for a Vermont fall road trip?

The foliage in Vermont usually peaks between late September and mid-October, but exact timing varies by region and elevation. Northern Vermont and higher elevations (like Stowe and Smugglers’ Notch) change first, while southern areas hold onto their colors a little longer. You can check this Vermont fall foliage map for up-to-date info.

🚗 How long does a road trip from Boston to Vermont take?

Driving from Boston to southern Vermont (Manchester area) takes about 3.5 hours. If you’re heading all the way to Stowe at the end of the trip, the drive back to Boston is roughly 3.5 to 4 hours, depending on traffic.

🗺 Is this Vermont fall road trip itinerary flexible?

Absolutely. You can shorten it into a 5-day trip if you’re short on time or stretch it out over 10 days to really slow down.

📸 Tips for leaf-peeping in Vermont

• Start your days early to avoid crowds at popular viewpoints.
• Always bring layers as it can be warm in the valleys and chilly in the mountains.
• Book hotels well in advance! Vermont’s fall foliage season is busy, and small-town accommodations fill up fast. For more info, check out my in-depth article on where to stay in Vermont in the fall.

Day 1: Boston to Manchester, Vermont

Your Vermont fall road trip kicks off in Boston, which is perfect if you’re flying into Logan Airport. You’ll want to rent a car right away so you can hit the road with ease.

I like using Discover Cars because it makes comparing rates and finding the right vehicle for a road trip from Boston to Vermont super simple.

Before heading out, grab a strong coffee and some snacks for the roughly 3.5-hour drive to southern Vermont.

If you’d like to break up the journey, stop in Brattleboro. This artsy town just over the border has a charming Main Street, local galleries, and cozy cafés. Perfect for stretching your legs and fueling up!

Once you arrive in Manchester, check into The Equinox Golf Resort & Spa for a touch of luxury or go for a cozy, historic vibe at Hampton Inn & Suites Manchester. Both make a great base for exploring the area.

Spend your afternoon at Hildene, The Lincoln Family Home. The mansion and surrounding trails are gorgeous with fall foliage and make a peaceful, scenic welcome to Vermont.

For dinner, try The Silver Fork, a warm spot known for its locally inspired dishes and craft cocktails. Afterwards, if you still have energy, drive up Skyline Drive on Mount Equinox for a sunset view over the rolling hills.

Day 2: Manchester to Woodstock

After breakfast in Manchester, hit the road for the next leg of your Vermont fall road trip. The drive to Woodstock takes about 2.5 hours, but it’s worth taking your time along the way.

Route 100 is one of the most scenic drives in Vermont, especially in the fall. Expect plenty of chances to pull over for photos of rolling hills, covered bridges, and colorful forests.

A great place to stop en route is Weston. This tiny village is home to the Vermont Country Store, a fun spot to browse for local snacks, maple products, and nostalgic New England goods.

Once you arrive in Woodstock, check into one of the charming inns in town (you’re going to have to book two nights here). Woodstock Inn & Resort is a classic choice if you’re looking for something upscale, while The Village Inn of Woodstock offers a cozier, more intimate feel.

Spend your afternoon exploring Woodstock’s picturesque center. Some of the best things to do in Woodstock are walking across the Middle Covered Bridge, wandering through boutique shops and art galleries, and stopping for a coffee at Mon Vert Café.

If there’s time before dinner, visit Billings Farm & Museum to see the historic barns and learn about Vermont’s farming traditions.

For dinner, head to The Prince & The Pauper, a long-time favorite in Woodstock with a seasonal menu that highlights local ingredients.

Day 3: Explore Woodstock and Quechee

Day 3 is all about slowing down and soaking up the charm of Woodstock and its surroundings.

Start your morning with a short hike up Mount Tom. The trail isn’t too long, and the views from the top are worth it, especially with the colorful fall foliage spread out below!

Next, drive a few minutes out of town to Sugarbush Farm. This family-run spot is a great place to sample award-winning cheeses and taste different grades of maple syrup. It’s a simple, authentic Vermont experience that always feels like a highlight.

In the afternoon, head over to Quechee Gorge, Vermont’s so-called “Little Grand Canyon.” Take in the view from the bridge or walk down the trail to the bottom for a different perspective.

Before leaving Quechee, stop by Simon Pearce. You can watch glassblowers at work in the workshop and grab a late lunch or snack at the riverside restaurant.

Return to Woodstock for a relaxed evening. Grab dinner at Worthy Kitchen, a casual spot with great comfort food and local craft beers.

Day 4: Woodstock to Burlington

Today, you’ll continue your Vermont fall road trip itinerary with one of the most scenic drives in the state. The route from Woodstock to Burlington takes about 3 hours, but you’ll want to allow extra time for stops along the way.

Make sure to stop at Cold Hollow Cider Mill in Waterbury. It’s one of the most popular roadside stops in Vermont, famous for its fresh apple cider and warm cider donuts. Grab a dozen for the car, you won’t regret it!

As you get closer to Burlington, the scenery shifts from rolling hills to lake views. Once in town, check into Hotel Vermont for a stylish stay near the waterfront or opt for something cozier like Hilton Garden Inn Burlington Downtown.

Spend the afternoon exploring Church Street Marketplace. This pedestrian-only street is lined with shops, restaurants, and street performers, giving the whole area a lively but laid-back vibe.

If the weather’s nice, taking a walk or renting bikes along the Lake Champlain waterfront for a perfect sunset view is hands down one of the best things to do in Burlington.

For dinner, try Hen of the Wood, one of Burlington’s most loved restaurants with a menu that celebrates Vermont’s seasonal ingredients.

Day 5: Burlington to Stowe via Smugglers’ Notch

On Day 5, it’s time to leave Burlington and head toward Stowe, one of the most iconic stops on any Vermont fall foliage road trip.

The drive only takes about 45 minutes if you go directly, but I’d recommend a slight detour.

Instead of heading straight to Stowe, drive north to Cambridge and Jeffersonville, then loop back down through Smugglers’ Notch Pass. This route adds a little time but rewards you with one of the most dramatic drives in Vermont!

The narrow, winding road through Smugglers’ Notch cuts between towering cliffs and dense forests that explode with color in the fall. It’s one of those stretches where you’ll want to pull over often for photos, so plan a bit of extra time.

Stowe is one of those charming small towns in Vermont that feels straight out of a movie. Check into a cozy base for the next two nights. Topnotch Resort is perfect if you’re after a little luxury, while Green Mountain Inn offers a historic vibe right in the heart of town.

Spend the afternoon exploring Stowe’s village center. Wander along Main Street, snap photos of the iconic Stowe Community Church, and grab a coffee at Black Cap Coffee Roasters. If there’s time, take a bike ride on the Stowe Recreation Path to enjoy the foliage from a different perspective.

For dinner, book a table at Harrison’s, a local favorite with a warm and welcoming vibe.

With 3 days in Stowe, you’ll have plenty of time to enjoy everything this area has to offer without feeling rushed.

Day 6: Exploring Stowe and Mount Mansfield

Now that you’ve made it from Boston to Stowe VT, it’s time to slow down and enjoy one of the most beautiful places to visit in Vermont in the fall.

Start your morning with a ride on the Stowe Gondola SkyRide, which takes you straight up Mount Mansfield, Vermont’s highest peak. The views from the top are incredible on a clear fall day, with rolling hills and fiery foliage stretching out in every direction.

If you prefer to drive, you can also take the Auto Toll Road up to the summit for a similar experience.

After soaking in the views, grab lunch back in town or stop at Idletyme Brewing for casual food and local beer.

Then spend your afternoon checking off more classic things to do in Stowe: walk or bike the Stowe Recreation Path, browse local shops and galleries, and make a quick stop at Gold Brook Covered Bridge. Known locally as Emily’s Bridge, it’s one of Vermont’s most photographed covered bridges and a fun little detour!

For dinner, head to the Trapp Family Lodge Bierhall. Their Austrian-inspired menu and cozy mountain setting make it the perfect spot to end a fall day in Stowe.

Day 7: Stowe to Boston with Scenic Stops

Your final day in Stowe is all about enjoying those last bits of Vermont charm before the drive back to Boston. Start your morning with a relaxed breakfast in town, then take a little time to wander the shops and pick up any last-minute souvenirs.

After breakfast in Stowe, it’s time to begin the drive back to Boston. But instead of rushing, make the most of your final day on this Vermont fall road trip by stopping at a few highlights along the way!

Your first stop can be the Ben & Jerry’s Factory in Waterbury. Even if you’re not up for a full tour, the scoop shop is worth it for a quick ice cream break – yes, even in the fall!

From there, continue on to Montpelier. This charming little capital is a great place to stretch your legs, grab a coffee, and snap a photo of the gold-domed State House framed by colorful foliage.

The total drive from Stowe to Boston takes around 4 hours, so plan to arrive back in the city by late afternoon or early evening.

If your schedule allows, I’d recommend spending a little time exploring Boston, too. It’s the perfect way to round out your New England adventure!