From Vermont’s golden lakeshores to New Hampshire’s mountaintop vistas, discover the ultimate New England fall foliage road trip across the USA’s most breathtaking autumn landscapes.
Autumn in New England isn’t just a season—it’s a performance, and every winding road is a front-row seat. Hillsides blaze with maple reds, birch golds, and oak ambers, while historic villages glow under canopies of late-afternoon light. This is where leaf-peeping meets indulgence: mornings start with warm cider and cranberry scones in a clapboard inn, afternoons linger in vineyard tastings or strolls through antique-lined main streets, and evenings end fireside with a glass of pinot as the wind rustles through the last of the season’s leaves. Along the way, detours tempt—oyster shacks on the coast, harvest suppers in candlelit barns, and art-filled towns that feel like they’ve been waiting just for you.
Stop 1: Lake Candlewood
Connecticut’s largest lake, Candlewood stretches across 8.4 square miles of shimmering blue, its shores wrapped in a quilt of autumn color. On the western edge, Squantz Pond State Park draws weekend wanderers who come for leisurely shoreline walks and panoramic leaf-peeping vistas. Further north, Brookfield and Sherman reveal a quieter charm—vineyards with timeworn grapevines spilling across sunlit hillsides. At White Silo Farm in Sherman, tastings lean toward the unexpected, with wines crafted from farm-grown raspberries, black currants, and rhubarb. Cross the water to Lover’s Leap State Park and you’ll find one of the area’s most romantic views—a short stroll over a storybook iron bridge delivers you to a lookout where the Housatonic River meanders below, framed in a blaze of fall foliage.
Where to Eat
American Pie Company tempts travelers with old-fashioned indulgence—twenty kinds of house-made pies (the pumpkin and blueberry crumb are local legends) plus hearty burgers, steaks, and fresh salads.
Stop 2: Kent
Tucked into the rolling Litchfield Hills along the Housatonic River, Kent has earned a reputation as one of the finest places in New England to witness autumn’s grand display. Dense woodlands wrap the town in a fiery embrace of reds, golds, and russets, best appreciated from the summit of Cobble Mountain in Macedonia Brook State Park. The climb is steep, but the payoff—panoramic views stretching to the Taconic and Catskill ranges—is worth every step. For something gentler, Kent Falls State Park offers a more leisurely path to spectacle. A short trail with multiple viewing platforms brings you up close to a 250-foot cascade, its whitewater framed by the season’s blazing palette. The famed Appalachian Trail also meanders through town; the Kent stretch delivers a tranquil, mostly flat five-mile ramble along the Housatonic, perfect for soaking in river views and the rustle of leaves underfoot.
Where to Stay
A short drive away in Falls Village, The Falls Village Inn blends small-town history with polished charm. Once a stopover for Housatonic Railroad travelers, its five guest rooms—styled by noted interior designer Bunny Williams—feel like a sophisticated retreat, wrapped in the quiet rhythm of countryside life.
Stop 3: Housatonic Meadows State Park
The Housatonic River is a study in transformation—wild and fast in spring, coaxing kayakers and canoeists into its rapids, then mellowing by summer into a glassy stretch beloved by fly-fishers. Come fall, it becomes something else entirely: a painter’s dream, its banks ablaze with the reds and golds of maples and oaks. In Housatonic Meadows State Park, campsites hug the water’s edge, while the Appalachian Trail slips quietly into the surrounding hills for those eager to wander under a canopy of color. For a truly local experience, Housatonic River Outfitters in Cornwall Bridge offers guided fly-fishing trips complete with gourmet picnics—equal parts sport and slow-living indulgence. Just upstream, West Cornwall’s historic covered bridge is a scene straight out of a New England postcard: weathered timbers arching over the broad river, framed by foliage so vivid it feels almost unreal.
Stop 4: The Berkshires
In the westernmost reaches of Massachusetts, the soft, rounded peaks of the Berkshires start their autumn transformation as early as mid-September—rolling waves of crimson, amber, and gold unfurling across the horizon. Great Barrington, the cultural heart of the region, blends small-town charm with cosmopolitan flair: its once-industrial streets now hum with art galleries, chic boutiques, and farm-to-table dining. It’s the perfect launch pad for an afternoon hike or a leisurely picnic in the nearby Beartown State Forest, where 12,000 acres of trails wind past quiet glades and the glassy expanse of Benedict Pond. Further north, October Mountain State Forest—Massachusetts’ largest protected green space—offers sweeping views and a name borrowed from Herman Melville himself, hinting at the time of year when its hillsides are at their most breathtaking.
Where to Eat
In Great Barrington, Prairie Whale serves modern American fare with a rustic, soulful touch. Housed in a converted family home, the space glows with dim light and a lived-in warmth, while the porch offers a breezy perch on golden autumn evenings. The menu changes with the seasons, and the owners’ commitment to local farms is evident in every inventive plate.
Stop 5: Mount Greylock State Reservation
At 3,491 feet, Mt. Greylock may not rival alpine giants in stature, but it more than makes up for it in drama. From the top of the 92-foot War Veterans Memorial Tower, the view spills out for nearly 100 miles—rolling across the Taconic, Housatonic, and Catskill ranges, brushing five states in a single sweep. On overcast days, the summit can feel like a secret above the clouds, its ridgelines bathed in unexpected light. The road to the top winds past scenic pull-offs—some leading to hidden waterfalls—making it easy to slip in a short hike before claiming the panoramic prize. In total, the reservation offers 45 miles of trails, including a storied stretch of the Appalachian Trail.
Where to Stay
Perched right at the summit, Bascom Lodge has been welcoming travelers since the 1930s, when it was built as a federal work project. Its stone-and-timber architecture blends perfectly with the mountain’s rugged profile, and the shared-bath rooms are simple but comfortable, with views that feel like they belong to the sky. Watching the sunset from here—surrounded by the quiet hum of wind through the peaks—is pure Berkshires magic.
Stop 6: Manchester
With its stately New England architecture and mountain backdrop, Manchester has a timeless elegance that only sharpens in autumn. For the region’s most commanding views, head south to the Mt. Equinox Skyline Drive—a winding 5.2-mile ascent to the 3,848-foot summit, the highest peak in the Taconic Range accessible by car. From the top, a 360-degree panorama sweeps across the Adirondacks, the Battenkill Valley’s patchwork fields, and, on clear days, all the way to Montreal’s Mt. Royal. Just outside town lies Hildene, the 412-acre Georgian Revival estate once home to Robert Todd Lincoln, the only surviving son of President Abraham Lincoln. Inside, rooms preserve presidential heirlooms and the quiet grandeur of another era, while outside, miles of wooded trails and manicured gardens melt into the Green Mountain horizon.
Where to Stay
For a refined yet intimate retreat, the Ash Street Inn B&B combines Victorian charm with modern comfort. Built in 1885 and lovingly restored, it offers plush robes, fine linens, and warm hospitality—just steps from the Currier Museum of Art.
Stop 7: Lake Champlain
Spanning 490 square miles across New York, Vermont, and Quebec, Lake Champlain is the kind of place where autumn feels infinite—its waters mirroring fiery hillsides and crisp blue skies. On the Vermont shore, Burlington makes an irresistible base. Stroll its lively downtown, then wander to the wooden lakefront promenade where four-person rocking benches invite you to slow down and watch the sailboats drift by. For a more active spin, rent a bike and follow the 7.5-mile lakeside path, where the scenery shifts from golden shoreline to wide-open water views. And for the most spectacular off-shore perspective, set sail aboard the Friend Ship with Whistling Man Schooner Company, gliding across the lake under a canopy of autumn color.
Where to Eat
Locals swear by City Market, Burlington’s vibrant gourmet co-op brimming with Vermont-made treasures. From farm-fresh produce to small-batch cheeses and craft beers, it’s a celebration of the state’s bounty. The sprawling deli and hot bar make it the perfect place to pack a picnic for your lakeside adventure.
Stop 8: Bretton Woods
Forget standing still—this is leaf-peeping in motion. At Bretton Woods, autumn isn’t just admired, it’s flown through. The year-round Bretton Woods Canopy Tour takes you deep into the forest on a guided adventure: a short hike, a walk across sky bridges, and a thrilling descent along 10 zip lines that whisk you from platform to platform, dropping as much as 1,000 feet at speeds up to 30 mph. If your appetite for altitude isn’t satisfied, cross US 302 and follow Base Road for six miles to one of New England’s most storied rides: the Mount Washington Cog Railway. Since 1869, this coal-fired, steam-powered marvel has been climbing to the 6,288-foot summit of Mt. Washington—the highest peak in the region. On a clear day, the views stretch across a tapestry of peaks and valleys, and in autumn, the mountainside looks like it’s been set ablaze by nature’s own hand.
Stop 9: North Conway
Framed by mountain ridges and laced with crisp alpine air, North Conway has a knack for pairing postcard views with cozy hospitality. Many of its best inns, pubs, and restaurants come with sweeping panoramas of the surrounding peaks—a backdrop that’s particularly spectacular in autumn. If you’re traveling with children, or if you missed the Cog Railway up Mt. Washington, the Conway Scenic Railroad offers a nostalgic alternative. Board the antique steam-powered Valley Train for a leisurely 11-mile round trip from North Conway to the village of Conway, with the Moat Mountains and the Saco River rolling by in a wash of seasonal color.
Where to Stay
Just a five-minute stroll from town, the Spruce Moose Lodge is all New England charm, housed in a spruce-green 1850s home. Choose from warmly decorated guest rooms, wood-floored cottages, or snug bungalows with Jacuzzis. For groups, there are even full houses available to rent—ideal for making this mountain town your autumn basecamp.
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