The Ultimate 7-Day New England Fall Road Trip Itinerary

Planning a 7 day New England fall road trip and want to see the region at its most colorful? Fall here means bright red, orange, and yellow leaves, winding scenic drives, and charming small towns worth stopping for.

This itinerary focuses on the best of Vermont and New Hampshire, two states known for their incredible foliage drives, quaint villages, and mountain views.

You’ll travel a loop starting and ending in Boston, with time to slow down and enjoy each stop.

Over the next week, you’ll wander through covered bridges, check out scenic overlooks, and drive some of the most famous foliage routes in the country.

I’ll guide you through the exact route, where to stay, and the top sights for each day so you can make the most of your fall road trip in New England.

Disclaimer: Some of the links in this post are affiliate links, which means I may earn a small commission if you make a purchase, at no extra cost to you.

Good to Know Before Your 7 Day New England Fall Road Trip

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

Peak foliage usually happens from late September to mid-October, but exact timing varies by region and weather. Northern Vermont and New Hampshire tend to change earlier, while southern areas peak a bit later. Check this peak fall foliage map before your trip to catch the colors at their best!

✈️ Where should you start your road trip?

This itinerary starts and ends in Boston, which has the biggest airport and plenty of rental car options. You could also start in Burlington, Vermont, if flights are cheaper or you want to cut out some driving, but Boston makes the most sense for this loop.

🚗 Do you need a car for this trip?

Yes 100%! Public transportation won’t get you to the scenic mountain roads, small towns, and covered bridges you’ll want to see. Renting a car also gives you the freedom to stop for photos whenever you spot an incredible view. Check Discover Cars for the best rates!

📍 How far apart are the stops on this itinerary?

Most drives are between 1 and 2 hours, with a few longer stretches. The scenery is a big part of the experience, so allow extra time for photo stops, short hikes, and exploring each town.

🏨 Where to stay along the route

You’ll spend two nights each in Stowe, Woodstock, and Lincoln, plus one night in Boston at the end of the trip. I’ve included hotel recommendations for each stop later in the itinerary, so you can easily find places that fit your style and budget!

📆 Should you book in advance or decide as you go?

Leaving accommodation to the last minute might give you more flexibility with the weather, but on the other hand, you risk not finding anything in popular foliage towns as places can sell out quickly. It’s a tough call, but I recommend booking everything in advance and choosing hotels with flexible cancellation policies so you can adjust if the forecast changes.

Day 1: Boston to Stowe

Kick off your 7 day New England fall road trip with a scenic drive from Boston up to the mountain town of Stowe, Vermont.

It’s about 3.5 to 4 hours without stops, but you’ll want to give yourself extra time for breaks and photo opportunities along the way.

If you have the time, a quick detour into Montpelier, the smallest state capital in the US, is worth it for a stroll past the gold-domed State House and the small cluster of local shops and cafés. From there, it’s a short scenic drive into Stowe.

Once you arrive, spend the afternoon exploring Stowe’s charming Main Street with its white church steeple, small boutiques, and cozy cafés.

Make sure to check out Emily’s Bridge (officially called Gold Brook Covered Bridge), a classic Vermont covered bridge that’s especially photogenic in the fall.

Settle in for the night at Green Mountain Inn, a historic property right in the heart of the village, or treat yourself to the mountain views and spa facilities at Topnotch Resort.

You’ll be staying in Stowe for two nights, so you have plenty of time to enjoy the area without rushing.

Day 2: Stowe and Smugglers’ Notch

Start the day with one of the most scenic fall drives in Vermont, Smugglers’ Notch. This narrow mountain pass twists between towering cliffs and dense forests, and in the fall, the whole route bursts with color.

The drive itself is not long, but you will want to allow plenty of time for photo stops at the scenic pull-offs. The road is usually open until late October, but it closes in winter, so check ahead if you are visiting toward the end of the season.

Before or after your drive, stop at the Stowe Community Church viewpoint. The white steeple with Mount Mansfield in the background is one of the most iconic shots of Stowe, especially when it’s surrounded by pretty fall colors!

If you have time, continue through the notch all the way to Jeffersonville for a short detour to see two beautiful covered bridges. The Historic Cambridge Junction Covered Bridge sits over the Lamoille River and is one of the most photographed in the area.

Just a few minutes away, the Historic Grist Mill Covered Bridge is smaller but equally charming, with a quiet setting that is perfect for a quick stop.

Back in Stowe, head up Mount Mansfield for panoramic views over the Green Mountains. You can take the gondola or drive the toll road to the summit for a fee. At the top, several short trails lead to even better viewpoints, so bring comfortable shoes if you want to explore.

In the afternoon, enjoy the Stowe Recreation Path on foot or by bike. The trail passes fields, rivers, and mountain views, and you can easily stop in town for coffee or a snack along the way.

End the day with dinner and drinks at one of Stowe’s local breweries, or make your way to the Trapp Family Lodge for Austrian-inspired food and a cozy atmosphere.

For more details, you might be interested in reading my ultimate 3-day Stowe itinerary or the best things to do in Stowe, Vermont!

Day 3: Stowe to Woodstock

On this part of your 7 day New England fall road trip, you’ll head south from Stowe to the postcard-perfect town of Woodstock. The drive isn’t long, which means plenty of time for a few classic Vermont stops along the way.

Start at Cold Hollow Cider Mill in Waterbury. The smell of fresh cider donuts hits you the moment you walk in, and it’s hard to leave without at least one! Pair it with a glass of hot or cold apple cider, then browse the shelves for maple syrup, jams, and other local treats.

A few minutes down the road, you’ll find the Ben & Jerry’s Factory. Take the short tour to see how the ice cream is made, sample a couple of flavors, and visit the quirky Flavor Graveyard out back. Even if you skip the tour, it’s worth stopping for a cone.

If you didn’t have time to visit Montpelier on Day 1, this is your second chance. Park near the gold-domed Vermont State House, take a quick stroll through the tiny downtown, and grab a coffee before continuing south.

Arrive in Woodstock in the afternoon and wander around The Green, cross the Middle Covered Bridge, and explore the small shops and cafés along Central Street.

This is one of the most charming towns on any New England fall foliage road trip, so take your time soaking in the atmosphere before dinner.

Settle in for two nights in Woodstock. The Woodstock Inn & Resort offers a beautiful central location, while The Shire Woodstock has comfortable rooms with peaceful river views just a short walk from the center.

Day 4: Woodstock and Quechee

Start your morning with breakfast at Mon Vert Café, a local favorite for fresh pastries, hearty breakfast plates, and great coffee.

From there, it’s a short walk to Billings Farm & Museum, where you can explore historic barns, meet the farm animals, and learn about Vermont’s agricultural history.

Next, make the short drive to Sugarbush Farm, known for its award-winning cheeses and pure Vermont maple syrup. You can sample different varieties, walk the maple trail to see how sap is collected, and browse the small farm store for gifts.

Continue to Quechee Gorge, one of Vermont’s most famous natural landmarks. Park by the bridge for an easy viewpoint, or take the trail down to the river for a different perspective.

A quick stop at the nearby Simon Pearce Glassblowing Studio is also worth it to watch artisans at work and enjoy the riverside setting.

On the way back toward Woodstock, stop at Taftsville Covered Bridge, one of Vermont’s oldest and most photogenic.

If you’ve seen photos from New England in the fall, chances are you’ve come across Sleepy Hollow Farm more than once. It’s one of the most scenic spots in the area, but access to the road has been limited to residents only in recent years, so it may not be possible to visit this year.

Wrap up the day with a relaxed evening in Woodstock. You can find more inspiration for your time here in my weekend in Woodstock itinerary and my guide to the best things to do in Woodstock in the fall!

Day 5: Woodstock to Lincoln and Franconia Notch

Leave Vermont behind this morning and cross into New Hampshire, trading rolling farmland for the dramatic peaks of the White Mountains. It’s about a 2-hour drive to Lincoln, your base for the next two nights, with plenty of fall color along the way.

Once in Lincoln, drop your bags at your hotel and head straight for Franconia Notch State Park, a must on any New England fall foliage road trip.

The main highlight is Flume Gorge, a narrow granite chasm with waterfalls, covered bridges, and a wooden boardwalk that winds right through the rock walls.

Flume Gorge requires a timed reservation booked in advance, so it’s best to plan your day around whatever slot you can get. If your entry time is later in the afternoon, you can swap the order of the day’s stops to make the most of the light.

Other easy sights in Franconia Notch include The Basin, a quick walk to a natural granite pothole in the Pemigewasset River, and the Cannon Mountain Aerial Tramway, which offers sweeping views over the White Mountains.

Aim to finish the day with the short but steep Artists Bluff Trail. The viewpoint looks over Echo Lake and the surrounding peaks and is especially beautiful in the golden light before sunset!

If you need more ideas, check out my guide about the best things to do in the White Mountains.

Stay two nights in Lincoln so you can explore the Kancamagus Highway tomorrow without backtracking.

The RiverWalk Resort at Loon Mountain has spacious suites and mountain views right in the center of town, while the Holiday Inn Express & Suites offers cozy rooms with a great location.

Day 6: Kancamagus Highway and Crawford Notch

Today is all about one of the most famous drives on a fall road trip in New England, the Kancamagus Highway. This 34-mile stretch between Lincoln and Conway is packed with mountain views, waterfalls, and scenic overlooks, and in peak foliage season it draws huge crowds.

It’s important to start early, ideally before 8 am, because once the parking lots fill up and the traffic builds, it can move at a crawl. On busy weekends, it’s not unusual to get stuck in traffic for three or four hours just trying to make it across!

Heading east from Lincoln, some of the best stops include Hancock Overlook, Sabbaday Falls, Rocky Gorge, and Lower Falls. There are plenty of scenic pull-offs too, so take your time and enjoy the views.

Instead of turning around in Conway and driving the same road back, I recommend continuing north to Crawford Notch State Park.

This detour not only adds more scenery, like Jackson’s charming covered bridge and the mountain views around Bartlett, but it also helps you avoid the worst of the afternoon traffic on the Kancamagus.

From Crawford Notch, loop back toward Lincoln for your final night in the White Mountains. You can find even more tips, maps, and detailed stop descriptions in my full guide to driving the Kancamagus Highway in the fall.

Day 7: Salem and Boston

On the final day of your 7 day New England road trip, leave Lincoln early and head south toward the coast.

Your first stop is Salem, Massachusetts, famous for its 17th-century witch trials and spooky seasonal atmosphere in October. The drive takes about 2.5 to 3 hours, so plan to arrive mid-morning.

In Salem, stroll through the historic streets lined with colonial-era homes and browse the shops on Essex Street. Popular stops include the Salem Witch Trials Memorial, the Witch House, and the waterfront area around Derby Wharf.

If you’re visiting Salem in October, expect big crowds and book any timed tickets for museums or attractions in advance. It’s the most popular town for Halloween after all!

After lunch, continue into Boston, just 30 to 40 minutes away. Spend the afternoon walking part of the Freedom Trail to see historic sites like Boston Common, Quincy Market, Faneuil Hall, and the Old State House.

If time allows, wander through Beacon Hill for its narrow cobblestone streets and classic brick rowhouses, or relax in the Boston Public Garden.

If you have an evening flight, you may only have a couple of hours in Boston, so choose a few highlights that appeal most to you.

If you’re staying overnight, enjoy dinner in the North End, Boston’s Italian district, before wrapping up your trip.

For an overnight stay, The Godfrey Hotel offers a stylish base close to the Freedom Trail, while Boston Park Plaza is a classic choice within walking distance of Boston Common.

In case you have more time in my city, you can check out my guide to one day in Boston or my 2-day Boston itinerary for more ideas!