The Perfect 5-Day Vermont Fall Road Trip Itinerary
A Vermont fall road trip is one of the best ways to experience New England during foliage season! The colorful mountain scenery is reason enough to visit, but the charming small towns, covered bridges, scenic drives, and cozy fall atmosphere make the trip even more special.
Five days gives you enough time to see several of Vermont’s most popular destinations without rushing or changing hotels every night. I recommend starting in northern Vermont and gradually moving south, following the general progression of the fall colors.
This guide covers everything you need to plan your Vermont fall vacation, including when to visit, where to stay, and a detailed 5-day Vermont fall road trip itinerary.
Disclosure: This post contains a few affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through my link.
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Good to Know Before a Vermont Fall Road Trip
Best time for a Vermont fall vacation
Let’s start with the bad news: it’s practically impossible to predict exactly when peak foliage will arrive. I know this is not what you want to hear, but unfortunately it’s the truth! The colors depend on temperatures, rainfall, elevation, and location, so the timing changes every year.
Peak foliage generally falls within the first ten days of October, but even that can vary. For this 5-day Vermont fall road trip, I would aim for sometime between October 5 and 15. Since the route travels from northern to southern Vermont, you have a better chance of finding good colors somewhere along the way.
I recommend checking the New England Fall Foliage Map for updates. However, foliage forecasts don’t become particularly useful until around mid-September, which creates a bit of a dilemma.
You can wait for a more reliable forecast and book at the last minute, but accommodation may be limited and expensive.
Alternatively, you can choose your dates well in advance for better availability and prices, accepting that peak foliage is never guaranteed. Unfortunately, there is no perfect solution when planning a Vermont fall vacation!
How to get to Vermont
Boston is the most convenient airport for this Vermont road trip as it usually has the best prices, and it’s the closest major international airport if you’re coming from overseas.
The drive from Boston to Stowe takes around 3.5 hours without stops. If your flight arrives around midday, picking up your luggage and rental car will likely take additional time, so you may not reach Stowe until the evening.
If you arrive later in the day, it’s better to spend the night near Boston and begin the drive the following morning.
Burlington Airport is much closer to Stowe and can work well for domestic travelers, although it offers fewer flights and often higher rental prices.
You’ll need a car for this Vermont fall foliage road trip, so I recommend picking it up straight at the airport. I recommend using Discover Cars to compare rental rates from different companies before booking!
How many days to spend in Vermont
As long as you can! Really, it’s such a magical place in the fall that you won’t want to leave. But I know that PTOs are limited, that’s why I put together this 5-day trip.
If you want to visit both northern and southern Vermont, including Stowe, Woodstock, and Manchester, I recommend spending at least five full days in the state.
It’s also best to allow an additional arrival day. Flying into Boston, collecting your rental car, and driving to Stowe can take most of the day, even if your flight arrives around midday.
If you have less time, I recommend choosing either northern or southern Vermont rather than trying to cover both. You can follow my 3-day Stowe itinerary for northern Vermont or my 3-day Woodstock itinerary for a shorter trip through southern Vermont.
Where to Stay on This Vermont Road Trip
I recommend choosing three bases for this itinerary:
- Stowe: 3 nights
- Woodstock: 1 night
- Manchester: 1 night
In Stowe, I recommend Green Mountain Inn if you want to stay directly in the village or Tälta Lodge for a modern lodge closer to the mountain.
For Woodstock, Woodstock Inn & Resort is the classic luxury choice in the center of town. On the River Inn is a more affordable alternative just a few minutes outside the village.
In Manchester, Kimpton Taconic Hotel is a beautiful Vermont-style hotel close to Hildene and the town center. Hampton Inn & Suites Manchester is a more practical option with breakfast included.
Fall is the busiest and most expensive season in Vermont, so book your hotels as early as possible, preferably with free cancellation!
If you can’t find accommodation in these towns, don’t worry. You’ll have a car, so you can also look for hotels within a 30-minute drive of Stowe, Woodstock, or Manchester.
Day 0: Arrival Day
Arriving in Boston
As I mentioned earlier, Boston usually offers the best selection of flights, especially if you’re traveling internationally, so I recommend starting your Vermont fall road trip here.
After landing at Boston Logan International Airport, collect your luggage and pick up your rental car. I recommend using Discover Cars to compare prices and find the best deal among the available rental companies!
If possible, book a flight that arrives by early afternoon. You’ll still need time to collect your luggage, and pick up your car before starting the drive to Stowe.
If your flight arrives later in the day, it’s better to stay near Boston Logan Airport and drive to Vermont the following morning. The journey is long enough that you don’t want to tackle it late at night after a full day of travel.
Drive to Stowe
The drive from Boston Logan Airport to Stowe takes around 3.5 hours without stops, although traffic around Boston can add extra time. Most of the journey follows I-93 and I-89, so it’s a straightforward drive.
If you arrive around midday, you’ll most likely reach Stowe in the early evening. Check into your hotel, have dinner, and get some rest before starting the itinerary the following morning.
You’ll spend three nights in Stowe, so there’s no need to squeeze any sightseeing into the arrival day. However, if you arrive earlier than expected, you can take a short walk around the village before dinner.
For where to stay, I recommend Green Mountain Inn if you want to stay in the heart of the village, or Tälta Lodge for a modern mountain lodge closer to the outdoor attractions.
Day 1: Stowe, Smugglers’ Notch & Mount Mansfield
Your first full day in Vermont combines the highlights of Stowe with two of the most scenic mountain areas in northern Vermont. Start early, as there’s quite a lot to fit in before finishing the day at Trapp Family Lodge.
Explore Stowe Village
Begin the morning in Stowe Village, where you’ll find the town’s famous white church, historic buildings, independent shops, and several cafés along Main Street.
Walk across the Giles W. Dewey Memorial Bridge for a lovely view of Stowe Community Church, then drive to the Stowe Community Church Viewpoint for the classic view of the church framed by the surrounding mountains and fall colors.
You can also stop at Café on Main for breakfast or coffee before continuing your day. Stowe Village is very small, so around one or two hours is plenty of time to walk around, browse the shops, and see the main sights.
Stowe also has a great craft beer and cider scene. Idletyme Brewing Company, The Alchemist Brewery, and Stowe Cider are all popular choices if you want to stop for lunch or pick up some local drinks. Just remember that you’ll still be driving for most of the day!
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Drive through Smugglers’ Notch
The drive through Smugglers’ Notch is short but incredibly beautiful, with a narrow, winding road surrounded by colorful forest and huge boulders. Route 108 runs through the mountain pass between Stowe and Jeffersonville, and there are several places where you can pull over to take photos or explore on foot.
Allow around one to two hours for the round trip from Stowe, depending on how often you stop. Parking is limited inside the notch, so only use the designated pull-offs.
The Sterling Pond Trail also begins at the top of the pass, but the hike takes around two hours. I would skip it on this itinerary so you still have enough time for Mount Mansfield and Trapp Family Lodge.
If you continue to Jeffersonville, you can also stop at the Historic Grist Mill Covered Bridge and Historic Cambridge Junction Covered Bridge before driving back through the notch. Both are really scenic!
Visit Mount Mansfield
At 4,395 feet, Mount Mansfield is the highest mountain in Vermont and one of the best places to see the fall colors from above! There are two main ways to reach the upper slopes: the Gondola SkyRide and the Auto Toll Road at Stowe Mountain Resort.
The gondola takes you to the Cliff House, while the 4.5-mile gravel toll road ends at a parking area on a different part of the summit ridge. Although they don’t arrive at exactly the same place, both offer panoramic mountain views, so simply choose the option you prefer.
Both experiences are quite expensive, though, especially if you’re traveling with several people. If you’re trying to keep your Vermont fall vacation affordable, you can skip Mount Mansfield and spend more time exploring the free viewpoints around Stowe and Smugglers’ Notch instead.
Allow around two hours for either option and check the opening hours and weather conditions before visiting. During peak foliage, it’s also a good idea to book gondola tickets in advance.
Stop at Trapp Family Lodge
Finish the day at the von Trapp Family Lodge & Resort, founded by the family whose story inspired The Sound of Music. The Austrian-style resort sits in the hills above Stowe and has beautiful views across the surrounding mountains.
Non-guests can visit the shops and restaurants without a property pass. For a relaxed late-afternoon stop, head to the von Trapp Bierhall for Austrian-inspired food and lager brewed on-site. Reservations are highly recommended during foliage season.
If you want to explore the resort grounds, you’ll need to purchase a day pass or book one of the guided experiences. The von Trapp History Tour is a good option for anyone interested in the family’s real story, but it takes around 90 minutes and should be reserved in advance.
Day 2: Waterbury & Burlington
Today’s route takes you south from Stowe for two classic Vermont food stops before continuing to Burlington for the afternoon. You’ll return to Stowe in the evening for your final night there.
See Gold Brook Covered Bridge
Before leaving Stowe, make a quick detour to Gold Brook Covered Bridge, also known as Emily’s Bridge. Dating back to 1844, it’s the oldest surviving covered bridge in Stowe and one of the prettiest places to photograph in the fall.
The bridge is also famous for its local ghost story. According to legend, a young woman named Emily was supposed to meet her lover here so they could run away together. When he never arrived, she took her own life, and her ghost is said to haunt the bridge to this day. Whether you believe the story or not, it certainly makes this covered bridge more memorable than most!
You can still drive across the bridge, but it’s narrow and only accommodates one direction at a time. There is a small parking area nearby, although spaces are limited, so visiting early in the morning is ideal. You’ll only need around 20 minutes here before continuing to Cold Hollow Cider Mill.
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Visit Cold Hollow Cider Mill
Cold Hollow Cider Mill is one of those places that feels made for a Vermont fall trip. The smell of fresh cider donuts hits you as soon as you walk inside, and yes, they’re absolutely worth trying!
You can wander through the mill at your own pace, watch apple cider and donuts being made, and sample the fresh cider for free. Production schedules vary, so the press might not be running during your visit, but you can still see how the process works.
There’s also a large country store packed with maple syrup, jams, cider products, and other Vermont-made treats. Across the road, the café serves breakfast and lunch, along with hard cider tastings. You could even skip breakfast in Stowe and eat here after visiting the covered bridge.
It gets extremely busy during foliage season, so arriving early makes the experience much more enjoyable.
Tour the Ben & Jerry’s Factory
Just ten minutes down Route 100, you’ll find the Ben & Jerry’s Factory in Waterbury. This is the company’s only factory open to the public, and it’s a fun stop even if you wouldn’t normally get excited about a factory tour!
The guided experience lasts around 30 minutes and covers the story of Ben & Jerry’s, how the ice cream is made, and a look over the production floor. You’ll also get to sample some ice cream at the end.
Tickets are released 14 days in advance and frequently sell out during foliage season, so set a reminder and book as soon as your date becomes available.
Before leaving, walk up to the Flavor Graveyard, where discontinued flavors have their own headstones and funny epitaphs. You can also stop at the Scoop Shop if the sample on the tour wasn’t quite enough.
If tour tickets are sold out, you can still visit the Flavor Graveyard, gift shop, and Scoop Shop without joining a tour.
Explore Burlington
Burlington is around 35 minutes from the Ben & Jerry’s Factory, giving you most of the afternoon to explore Vermont’s largest city. It’s compact and easy to see on foot, so park near downtown and leave the car there until you’re ready to return to Stowe.
Spend some time walking along Church Street Marketplace, a pedestrian street lined with shops, cafés, restaurants, and colorful historic buildings. From there, it’s around a ten-minute walk downhill to the Lake Champlain waterfront.
The waterfront is my favorite part of Burlington! Walk through Waterfront Park, follow a section of the Burlington Greenway, or simply find a bench and enjoy the views across the lake toward the Adirondack Mountains.
If the schedule works, you can finish the day with a sunset sailing cruise on Lake Champlain. Otherwise, stay for sunset along the waterfront and have dinner downtown before driving back to Stowe.
If you want to add more stops or spend longer in the city, you can find plenty of additional ideas in my guide to the best things to do in Burlington.
Day 3: Drive from Stowe to Woodstock
Today you’ll leave northern Vermont and continue south to Woodstock, where you’ll spend the night. The direct drive takes around 1.5 hours, but you can break it up with a short detour to Montpelier along the way.
Optional stop in Montpelier
Montpelier sits conveniently along the route from Stowe to Woodstock, so it’s an easy place to stop without adding much extra driving. As the smallest state capital in the United States, it’s compact enough to explore in an hour or two.
The main landmark is the Vermont State House, an impressive Greek Revival building topped with a gold dome. Take a look from the lawn, then walk along State Street and through the small downtown area, where you’ll find independent shops and cafés.
If you have more time, you can also visit Hubbard Park and walk up to its stone observation tower. Otherwise, grab a coffee, stretch your legs, and continue to Woodstock. If you prefer a slower afternoon in Woodstock, you can simply drive past Montpelier and continue south.
Explore Woodstock Village
Woodstock is one of the prettiest towns in Vermont, with historic homes, white churches, and tree-lined streets that look especially beautiful in the fall. Check into your hotel first, then spend an hour or two exploring the compact village on foot.
I recommend staying in Woodstock for one night. Woodstock Inn & Resort is the classic luxury choice in the center of the village, while On the River Inn is a more affordable option just a few minutes away by car.
Before walking around the village, visit Billings Farm & Museum, a working dairy farm and outdoor history museum just outside the center. You can meet the Jersey cows, sheep, goats, and draft horses, explore the restored 1890 Farm Manager’s House, and learn about Vermont’s farming history.
Back in the village, start around the Village Green and follow Central Street past the small shops, galleries, cafés, and historic buildings. Don’t miss Middle Covered Bridge, which sits right in the center of town and is open to both cars and pedestrians.
You can also walk past the Norman Williams Public Library and admire the beautiful homes along The Green and Elm Street. Woodstock is small, so you don’t need a strict route or more than a few hours to see the center before driving out to Taftsville and Quechee.
See Taftsville Covered Bridge
Taftsville Covered Bridge is less than ten minutes from Woodstock and sits directly along the route to Quechee. Built in 1836, it’s one of the oldest covered bridges in Vermont and easily recognizable by its bright red exterior.
You can drive through the bridge before pulling over nearby to take a closer look. The surrounding river, historic buildings, and colorful trees make this a lovely photo stop during a fall Vermont trip.
There isn’t much else to do here, so around 15 to 20 minutes is plenty before continuing to Quechee Gorge. If you want a quick snack or drink, you can also stop at the Taftsville Country Store nearby.
Visit Quechee Gorge
Quechee Gorge is one of those stops that can be as quick or as long as you want it to be! If you’re short on time, simply walk onto the Route 4 bridge and look down at the Ottauquechee River, which flows 165 feet below. The surrounding forest makes the view even better during fall foliage season.
You can park for free at the Quechee Gorge Visitor Center, right next to the bridge. There are sidewalks on both sides, so make sure to check the view in each direction.
For a closer look, follow the Quechee Gorge Trail down toward the river. The full trail is around 1.3 miles, but you don’t have to walk the entire thing. You can explore a short section and turn back whenever you’re ready.
Allow around 30 minutes for the bridge and viewpoints, or closer to an hour if you include part of the trail. Afterward, drive back to Woodstock for dinner and your overnight stay.
Day 4: Drive from Woodstock to Manchester
Today you’ll continue south from Woodstock to Manchester, stopping at a maple farm and one of Vermont’s best-known country stores along the way. You’ll then spend the afternoon exploring Manchester and visiting Hildene before staying overnight in town.
Visit Sugarbush Farm
Sugarbush Farm is a family-run maple and cheese farm hidden along the country roads outside Woodstock. The drive from the village takes around 15 minutes and is especially beautiful in the fall.
Admission is free, and you can sample several grades of maple syrup and different varieties of cheese before browsing the farmhouse shop. It’s a great place to pick up maple syrup, preserves, mustard, or other Vermont-made products to take home.
Maple syrup is produced in spring rather than fall, but the sugarhouse remains open for self-guided visits. You can learn how the trees are tapped, watch a short video about the process, and walk the easy 15-minute maple trail through the woods. There’s also a longer trail if you have more time.
Stop at The Vermont Country Store
The drive from Sugarbush Farm to Weston takes around an hour, following scenic roads through central Vermont. Once you arrive, head straight to the original Vermont Country Store, which has been welcoming shoppers here since 1946.
This isn’t just a regular souvenir shop. The shelves are filled with old-fashioned sweets, local cheeses, maple products, home goods, clothing, toys, and all kinds of nostalgic items you probably haven’t seen in years. It’s easy to lose track of time while browsing!
Weston itself is also lovely, with a small village green, white church, and historic buildings clustered around the store. Take a quick walk around before continuing south to Manchester. If you’re ready for lunch, you’ll also find food options next to the store.
Tour Hildene
Hildene is one of the most interesting historic attractions in southern Vermont. Built in 1905, the Georgian Revival mansion served as the summer home of Robert Todd Lincoln, the only one of Abraham and Mary Todd Lincoln’s four sons to survive into adulthood.
General admission includes a self-guided tour of the house, where many of the original furnishings are still on display. Beyond the mansion, you can walk through the formal gardens, visit the restored Pullman train car, and explore the working farm with its herd of Nubian goats.
The estate is much larger than it first appears, so allow at least two hours or closer to three if you want to see everything. The views across the Battenkill Valley are also beautiful during fall foliage season.
Hildene closes at 4:30 pm during October, so aim to arrive by early afternoon. Guided house tours are available at selected times, but the self-guided option gives you more flexibility on a road trip day.
Explore Manchester
Manchester makes a great final overnight stop on this Vermont road trip. Check into your hotel after visiting Hildene, then spend the rest of the afternoon and evening exploring the town.
I recommend staying in Manchester for one night. Kimpton Taconic Hotel is a beautiful boutique option in historic Manchester Village, while Hampton Inn & Suites Manchester is a more practical choice close to the shops and restaurants.
Manchester is divided between the quieter historic village and the busier town center. Walk along Main Street to see the white church, elegant homes, and classic New England buildings before heading into Manchester Center.
The town center has plenty of shops, cafés, and restaurants, along with several designer outlets. Northshire Bookstore is also worth visiting and is one of the best independent bookstores in Vermont.
Finish the day with dinner in Manchester and get an early night, as tomorrow’s route through southern Vermont is the longest day of the trip!
Day 5: Southern Vermont & Return to Boston
The final day follows a scenic route through southern Vermont before returning to Boston. It’s the longest day of the trip, so leave Manchester early and plan to reach Mount Equinox when the Skyline Drive opens.
Drive the Mount Equinox Skyline Drive
The Mount Equinox Skyline Drive is a 5.2-mile toll road that climbs more than 3,000 feet to the highest summit in the Taconic Range. The entrance is only around ten minutes from Manchester, making it an easy first stop of the day.
The road is paved but very steep and winding, with several viewpoints along the way. At the 3,848-foot summit, you’ll find the Saint Bruno Scenic Viewing Center and panoramic views across Vermont, New York, New Hampshire, and Massachusetts on a clear day.
Allow around 1.5 to 2 hours for the return drive, including time at the viewpoints and summit.
The Skyline Drive opens at 9 am and operates weather permitting. Since it’s fairly expensive and the views are the main reason to visit, I would skip it if the summit is covered in clouds or fog. Check the current conditions before leaving Manchester!
Explore Bennington
Instead of driving straight back to Boston after Mount Equinox, I recommend taking a small detour south to Bennington and then following Route 9 across southern Vermont. It adds some time to the journey, but the route is far more interesting than simply heading for the highway.
Bennington is around 35 minutes from the Mount Equinox Skyline Drive. Its most famous landmark is the 306-foot Bennington Battle Monument, which commemorates an important American Revolutionary War victory. You can see the monument from across town, and there’s an elevator to the observation level if you want another panoramic view.
Nearby, stop at the Old First Church and walk through the cemetery behind it, where poet Robert Frost is buried. The historic homes and tree-lined streets around Old Bennington are also lovely in the fall.
Bennington has three covered bridges within a few miles of one another: Silk Road Covered Bridge, Paper Mill Village Bridge, and Henry Covered Bridge. You probably won’t need to visit all three, but it’s easy to add one or two before continuing east toward Brattleboro.
Follow Route 9 Through Southern Vermont
Route 9 between Bennington and Brattleboro is also known as the Molly Stark Scenic Byway. The 48-mile road crosses the Green Mountains and is one of the prettiest ways to finish a Vermont fall road trip.
The first part of the drive climbs through the Green Mountain National Forest before reaching Wilmington, a small town with colorful historic buildings, independent shops, and cafés. Park near the center and take a quick walk around before continuing east.
Harriman Reservoir is another possible detour near Wilmington if you want to see the fall colors reflected on the water. A little farther along Route 9, stop at the Hogback Mountain Scenic Overlook for the famous “100-mile view” across Vermont, Massachusetts, and New Hampshire.
You don’t need to stop everywhere along the byway. Pick the places that interest you most and leave enough time to explore Brattleboro before continuing to Boston.
Stop in Brattleboro
Brattleboro is the last Vermont stop before you join the interstate for the drive back to Boston. It has a completely different feel from Stowe or Woodstock, with a more lively downtown known for its independent shops, galleries, bookstores, and cafés.
On the way into town, stop briefly at Creamery Covered Bridge. Built in 1879, it’s now closed to vehicles but remains open to pedestrians, making it easy to walk through and photograph.
Continue into downtown and take a stroll along Main Street, where colorful historic buildings overlook the Connecticut River. If you arrive before closing, you can also visit the Brattleboro Museum & Art Center inside the former train station.
Drive Back to Boston
From Brattleboro, join I-91 south before connecting with the Massachusetts Turnpike toward Boston. The drive takes around two hours without traffic, although delays are common as you approach the city.
If you’re flying home the following morning, stay near Boston Logan Airport and return your rental car either that evening or before your flight.
You can also add a few days in Boston after your Vermont fall road trip if you haven’t explored the city yet! You can check out my guide to the best things to do in Boston or if your schedule is tighter, follow my one-day Boston itinerary instead.
