Everyone dreams of a bucket list New England fall foliage road trip — and last year, my friends and I finally took our group trip out of the group chat and made it happen.
There were five of us, all juggling full-time jobs and limited PTO, so we had to be strategic with our planning. The good news? This 4-day itinerary only requires 3 PTO days and still manages to pack in some of the best fall foliage spots in New England.
From scenic drives and cozy small towns to picture-perfect leaf-peeping stops, here’s exactly how we made the most of a long weekend in New England in the fall.
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Want a quick peek at what this PTO friendly 4-day New England fall foliage road trip looks like in action? This video will give you a taste of the views, vibes, and must-see stops you can expect on your own New England fall getaway.
The best month to see fall foliage in New England is generally October — especially the first two to three weeks. This is when you’ll find the most vibrant reds, oranges, and golds across much of the region.
That said, peak color depends on the state (and even the elevation). Northern areas like Vermont, New Hampshire, and Maine usually see peak foliage in late September to early October, while southern New England — including Massachusetts, Rhode Island, and Connecticut — tends to peak in mid to late October.
As for how long fall lasts in New England, you can usually enjoy colorful leaves for about 6–8 weeks in total, starting in mid-September in the north and wrapping up in late October in the south.
Tip: Check state foliage trackers when planning your trip — these are updated weekly during the season and can help you hit peak color during your visit.
For your New England fall foliage road trip, the best airport to fly into is Boston Logan International Airport (BOS). Boston is the ideal starting point with easy access to scenic drives and charming towns throughout New England.
Starting your road trip in Boston means you can explore the city’s fall charm after going on a scenic drive and exploring the quaint towns across Massachusetts, Vermont, and beyond.
To make the most of your New England fall foliage road trip, renting a car is essential. Many of the best fall foliage locations are spread out across rural and small-town New England, where public transportation options are limited.
Having a rental car gives you the flexibility to follow the most beautiful scenic routes at your own pace and truly experience all the iconic spots this road trip offers.
Tip: Book your rental car early, as demand is high during the peak foliage season.
If you’re planning a New England fall foliage road trip but don’t have endless vacation days, this 5-day itinerary is the perfect solution. My friends and I only used 3 PTO days to make it happen, and we still squeezed in some of the dreamiest leaf-peeping towns in Massachusetts and Vermont.
We took a red-eye flight into Boston and picked up our rental car as soon as we landed. From Boston Logan Airport, it’s only about a 40-minute drive to Salem—super easy to get to and the perfect first stop for a Halloween-inspired New England fall foliage road trip!
October is the month to visit Salem, thanks to its witchy history, cozy coffee shops, and festive Halloween vibes. We strolled through the historic downtown, stopped by the Salem Witch Museum, and grabbed cider donuts
Once in Salem, we had to book the best walking tour (highly recommend doing this in advance since spots fill up fast). The tour was the perfect mix of history and spooky vibes, and it felt like the whole town was alive with Halloween spirit.
The best part of this walking tour? Seeing real-life filming locations from one of the most beloved Halloween movies of all time—“Hocus Pocus.” It honestly felt like stepping right into the movie set!
After soaking up all the witchy history and festive vibes, we made the 3.5-hour drive to our cozy Airbnb in Stowe, Vermont, to kick off the next part of our fall getaway.
Stowe is the perfect home base to explore this part of New England for the weekend and a great landing spot for your New England fall foliage road trip.
We kicked off the morning at the iconic Cold Hollow Cider Mill, one of Vermont’s must-visit stops on any New England fall foliage road trip. This family-owned mill has been around since 1974, and it’s famous for its fresh cider and homemade treats.
We grabbed breakfast in their café, and the pancakes were out of this world—especially when topped with their local maple syrup. I couldn’t resist buying their pancake mix to bring a little taste of Vermont home with me!
After breakfast, we browsed their shop, which is filled with all things maple, apple, and cozy New England goods.
Next, we made our way to Percy Farm Corn Maze, a classic fall activity that’s perfect for this time of year. Wandering through the tall stalks while surrounded by colorful foliage was so much fun!
Definitely one of the best seasonal activities you can do in Vermont during fall!
We toured the Nebraska Knoll Sugar Farm, a small, rustic maple farm tucked away in the countryside. The owners walked us through the process of making maple syrup and explained the differences between golden, amber, and dark syrups.
The tour ended with a tasting (the dark syrup was our favorite), and of course, we had to buy some to take home.
In the afternoon, we headed into downtown Stowe, which is straight out of a Hallmark movie. The town is filled with charming boutiques, cafés, and postcard-worthy scenery. A few must-see spots include:
The iconic view of Stowe Community Church – the white steeple framed by vibrant fall foliage is one of the most photographed spots in Vermont.
The Stowe mural – a colorful piece of street art that perfectly captures the spirit of the town.
Wandering Main Street – lined with shops and restaurants that feel cozy and quintessentially New England.
We wrapped up the day with dinner at the Trapp Family Lodge, a property founded by the von Trapp family (yes, from The Sound of Music). The Austrian-inspired lodge has sweeping mountain views and hearty meals that are the perfect ending to a crisp fall day.
Just be sure to make a reservation in advance, as this is one of the most popular dining spots in Stowe.
Between maple syrup tastings, corn mazes, and charming small-town vibes, day two of our New England fall foliage road trip felt like autumn at its very best.
We kicked off Day Three of our New England fall foliage road trip with one of the most breathtaking drives in Vermont — the famous Smugglers’ Notch mountain pass. This winding route cuts right through the mountains and is lined with towering cliffs, vibrant trees, and incredible viewpoints.
It felt like every bend in the road revealed another postcard-worthy scene, so of course, we made plenty of stops along the way to snap photos of the colorful fall foliage.
Next, we headed to Stowe Mountain Resort for the Gondola Skyride. Floating high above the treetops gave us a whole new perspective of Vermont’s autumn colors!
If you’re planning a fall trip to Vermont, this experience is an absolute must. And make sure to get there early, because the line to ride the gondola gets LONG!!!
In the afternoon, we took a short drive to Montpelier, the smallest state capital in the U.S., and explored its charming downtown. The local shops, cozy cafés, and historic architecture made it the perfect stop to slow down and enjoy small-town Vermont vibes.
After a full day of sightseeing and scenic drives, we returned to our Airbnb in Stowe for a relaxing night in — the perfect way to recharge before another day of adventures on our fall foliage road trip through New England.
We said goodbye to Stowe and continued with our fall foliage road trip. Our first stop of the day was the Ben & Jerry’s Factory in Waterbury (just a short drive from Stowe).
If you’re planning to go, definitely book your tour in advance — and if possible, grab the first time slot of the morning before it gets busy.
After indulging in some sweet treats, we continued our drive to South Royalton, Vermont. Fans of Gilmore Girls might recognize this spot — the white church from the opening credits can be found here!
It’s a tiny town, but surrounded by stunning Vermont fall foliage, which made the stop on our fall foliage road trip through New England extra special and a great addition to your fall foliage road trip.
From there, we made our way to Sugarbush Farm, where we were able to stroll the grounds, sample some local products, and take in more sweeping fall colors.
This is such a peaceful stop and really captures the essence of your fall foliage road trip through New England.
Our next highlight of the day was Woodstock, Vermont, and honestly, I wish we had carved out more time here! This charming town is filled with boutique shops, cafes, and some of the most photogenic covered bridges in New England.
If you’re looking for a postcard-worthy fall destination, Woodstock needs to be on your fall foliage road trip through New England.
After exploring Woodstock, we hit the road again and ended our day in Boston, Massachusetts. This gave us a perfect launch point for the next part of our fall foliage road trip through New England.
If you have more time, you could easily spend another night in Vermont to soak in even more of that fall beauty.
Our final day of this New England fall foliage road trip was spent in the city of Boston before catching our flight in the late afternoon.
After days of driving through colorful mountain passes, charming small towns, and scenic countryside, ending the trip in Boston felt like the perfect way to balance nature with a bit of city energy.
Even with only a few hours to spare, Boston is such a walkable city that you can cover a lot in a short amount of time. Here are some of the highlights you can do in Boston in one day (or even just a few hours):
Walk part of the Freedom Trail – This 2.5-mile trail connects 16 of Boston’s most historic landmarks, including Boston Common, the Massachusetts State House, and Faneuil Hall. Even if you don’t do the whole thing, picking a section gives you a great glimpse into the city’s history.
Explore Quincy Market & Faneuil Hall – A quick stop here lets you enjoy street performers, shops, and a wide variety of local eats.
Visit the Boston Public Garden – If you’re craving a bit more nature after your foliage-filled adventure, the gardens are especially lovely in the fall with colorful leaves and crisp air.
Stroll through the North End – Boston’s “Little Italy” is packed with charm, and if you have time, grab a cannoli from the famous Mike’s Pastry or Modern Pastry.
Check out the Boston Tea Party Ships & Museum – A fun, interactive stop that lets you learn about one of the most iconic moments in American history.
After a morning of sightseeing, we headed to the airport. From mountain passes in Vermont to coastal towns in Maine and the vibrant energy of Boston, this New England fall road trip itinerary was the perfect mix of nature, small towns, and city life.
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