By Stephanie McKeon, COO, Joshua’s Worldwide
New England in the fall is nothing short of magical. From rolling mountain ranges to charming small towns and winding riverside roads, the region becomes a canvas of fiery reds, golden yellows, and deep oranges. It’s why leaf peeping has become one of the most popular seasonal activities in the Northeast. Visitors travel from all over the country to take in the sights and smells of autumn.
If you’ve ever tried to plan your own leaf-peeping adventure, you know the challenges: crowded roads, tricky parking, and trying to navigate while also hoping to catch every view. At Joshua’s Worldwide, we believe the journey should be just as enjoyable as the destination. That’s why we offer not just luxury transportation, but full travel concierge services. We handle every detail from the route, the stops, the reservations, and the rides, so you can relax and take in the view.
To help you plan your perfect fall getaway, here are four of the best fall foliage drives in New England, complete with travel tips, must-see stops, and ideas for making the most of your leaf-peeping adventure.
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The Kancamagus Highway (New Hampshire)
Often simply called “The Kanc,” the Kancamagus Scenic Byway is a legendary destination for leaf peepers. Officially a 34.5-mile segment of NH Route 112, this National Scenic Byway winds through the White Mountain National Forest, climbing nearly 3,000 feet to Kancamagus Pass. It’s one of the most celebrated fall foliage drives in New England — with endless forests, scenic overlooks, and rich history along the way.
What You’ll See
- Sabbaday Falls & Rocky Gorge – Popular short hikes leading to waterfalls and rushing river views.
- Russell-Colbath Historic Site – A preserved 19th-century homestead that tells the story of early settlers in the region.
- Swift River & Hancock Branch – Serene stretches of water that reflect the fiery autumn leaves.
Concierge Touch
Fall is the busiest season along the Kancamagus, and timing can make all the difference. While you could drive the route in just about an hour, most visitors prefer to spend half a day or more exploring its overlooks, trails, and historic sites.
With Joshua’s, the journey unfolds at your pace. Pause for photos at scenic pull-offs, enjoy a short hike to a waterfall or end the day with dinner in nearby North Conway. Rather than keeping your eyes on the road, you’ll be free to take in the White Mountains’ most brilliant autumn colors.
Route 100 (Vermont)
Often called “Vermont’s Main Street,” Route 100 is one of the most scenic drives in the state. Stretching nearly the length of Vermont, this winding byway takes you on a true journey. The valleys lined with sugar maples, rolling farmland, and mountain towns all come alive in the fall. The covered bridges and roadside farm stands add to the charm. All in all, Route 100 is a fan favorite for leaf peepers seeking both beauty and authenticity.
What You’ll See
- Waterbury – A hub for cideries, craft breweries, and even the famous Ben & Jerry’s.
- Waitsfield – Quintessential Vermont, complete with red barns, covered bridges, and open fields framed by mountains.
- Stowe – A postcard-perfect ski town known for its fall festivals, hiking trails, and farm-to-table dining.
Concierge Touch
Route 100 offers countless opportunities to linger, and the best trips take advantage of them. While the drive could be completed in a few hours, most travelers stretch it into a full day if you’re stopping for tastings, photos, and leisurely walks through the villages. With Joshua’s Worldwide, your itinerary can include many fun stops along the way. This includes a cider flight in Waterbury, cheese sampling in Waitsfield, and a dinner reservation in Stowe. All seamlessly timed with transportation so you never feel rushed. The focus stays on Vermont’s most brilliant fall scenery, not the logistics.
The Mohawk Trail (Massachusetts)
Dating back more than a century, the Mohawk Trail is one of America’s first designated scenic byways and remains one of the best for Massachusetts fall foliage drives. Stretching over 60 miles across the northern Berkshires, it combines winding mountain roads with rich history and sweeping valley views. The drive is especially beloved in October, when the hillsides erupt in color.
What You’ll See
- Hairpin Turn – A dramatic curve on Route 2 in North Adams, 1,700 feet above sea level, offering panoramic views of the Hoosac Valley, Mount Greylock, and surrounding peaks, especially stunning in prime foliage season!
- Shelburne Falls – A charming small town known for its famous Bridge of Flowers, artisan shops, and galleries, perfect for a leisurely stroll between scenic stops.
- Mount Greylock – At 3,491 feet, Massachusetts’ highest peak features an observation tower with sweeping vistas across several states, framed by vibrant fall colors.
Concierge Touch
The Mohawk Trail can be driven straight through in a couple of hours, but its charm lies in the stops along the way. Most travelers take half a day to enjoy the overlooks, browse the small towns, and maybe hike a short trail. With Joshua’s, the experience is as flexible as you’d like. Whether that means a photo stop at the Hairpin Turn, a stroll through Shelburne Falls, or ending with a quiet dinner overlooking the Berkshires, you’ll enjoy the views while we handle the winding roads.
The Connecticut River Valley (Connecticut)
A coastal-meets-country route, the Connecticut River Valley offers a more intimate leaf-peeping experience. The winding riverside roads, vineyard-dotted hills, and historic towns are idyllic. It’s the perfect ideal option for those who want fall colors with a side of New England charm. The foliage here glows against the water, making it one of the region’s most scenic drives.
What You’ll See
- Essex – Colonial architecture, boutique shops, and the iconic Essex Steam Train & Riverboat.
- Old Saybrook – A coastal town where the Connecticut River meets Long Island Sound.
- Chester – A creative village known for its art galleries, cafés, and welcoming Main Street.
- Haddam – Home to the storied Gillette Castle, with panoramic views over the river.
Concierge Touch
The valley can be explored in just a couple of hours. However, the best trips leave time for vineyard tastings, riverboat rides, and lingering in the town centers. With Joshua’s, your day might include a stop for wine in Essex, a gallery stroll in Chester, and dinner reservations overlooking the water. The drive flows seamlessly, allowing you to enjoy the quiet beauty of Connecticut’s countryside without the distractions of planning or navigating.
Ready to See New England in Full Color?
Fall in New England is short but spectacular. The best way to experience it is with a journey designed around you. If you’re dreaming of winding mountain roads, riverside towns, vineyard tastings, or cozy dinners after a day of leaf peeping, Joshua’s makes it seamless.
Let us curate your fall foliage escape so every detail is handled, leaving you free to simply enjoy the view.
👉 Plan Your Leaf-Peeping Experience
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