10 New England Fall Road Trip Destinations

10 New England Fall Road Trip Destinations

There’s no wrong time or season for a New England road trip through its tiny towns and along its rocky and rugged coast, but the region sure does seem dressed up in its finest colors during the gorgeous foliage season.  So come along on a cool autumn cruise to one of these 10 New England Fall Road Trip Destinations!

Woodstock, VT
Vermont’s checkerboard of covered bridges come alive with autumnal flourishes like nothing else in New England. Two of Vermont’s 100 remaining covered bridges (down from it’s 19th century high of 600!) cross the Ottauquechee River in Woodstock.  Come for the picture-perfect views of iconic Vermont scenery—farmland, rushing rivers, bridges, and autumn colors all together—but be prepared to fall in love with Woodstock’s quaint, shop-lined downtown.  The perfect bag for this adventure?  Our stylish yet rugged Raymond White Tote Bag to carry all those local goods you stock up on— like fresh Maple Syrup!  

Camden, ME
An hour and a half up the mid-coast, Camden is an easy and low-key drive from Portland.  You’ll find a picturesque harbor lined with sail boats, a gorgeous colonial-style brick library, and classic New England church steeples rising above the low-lying Camden foothills. Take a quick drive up the Mount Battie auto road for a panoramic view of West Penobscot Bay awash in autumnal colors. Staying a night? You may just have time for a harbor cruise one of the cities famous schooners. 

Sugar Hill, NH
Tucked into the western reaches of Franconia Notch just beyond the White Mountain National Forest, Sugar Hill is a tiny village with a big pedigree: sweeping views of the Presidential, Kinsman, Franconia, and Dalton Ranges.  Though stunning year-round (lupine season is a must, as well!), the dramatic swaths of color over the mountains makes for a perfect drive through rural New Hampshire.  Be sure to check out the world-famous Polly’s Pancake Parlor, too.  

Rockport MA New England Wharf

Bradley Wharf in Rockport, MA. Photo by Cam Fattahi.

Portsmouth, NH
New Hampshire’s coastline is just over 18 miles long and Portsmouth shines bright as the state’s crown jewel of coastal culture and colonial-era bijou. Vibrant tones from its tree-lined streets meet federal-style brick manors and shops in Portsmouth’s growing downtown with an up-and-coming food scene.  Cruise the coast for iconic views, take a quick stop to tour a colonial farm-turned-hiking preserve, and hit the streets for oyster bars and cobblestone patio cocktails. 
Moosehead Lake, ME
Before a flourish of winter sports addicts crowd the region, take a peaceful and far-flung foliage drive along the shores of Moosehead Lake.  Mt. Kineo’s sheer cliffs dive right into the lake’s pristine waters, making for stunning fall photography.  Look for quiet cabin rentals and glamping experiences tucked into the lake’s many coves and bays for an overnight foliage getaway; there’s nothing quite like waking up to morning mist, loon calls, and moose sightings while Maine’s crisp autumn air fills your lungs. 
Burlington, VT
Along the bucolic shores of Lake Champlain, just across the New York border, Burlington’s gorgeous downtown is a fitting end point to the long quiet drive through Vermont’s autumnal farmscapes.  The state’s largest city and cultural hub, Burlington has something for everyone: the expansive and well-curated Shelbourne Museum, sidewalk-lined markets around Church Street, and a reputation for top notch outdoor activities.  Hike, bike, or canoe the region’s pristine trailways and waterways before a brewery tour and a bistro dinner overlooking the lake. 
Northampton, MA
A bustling center for collegiate studies with a vibrant arts and culture scene, Northampton somehow always feels like a small town waiting for you to explore.  With farm stands, horse barns, and miles of hiking trails dotting the landscape, campus buildings for the region’s consortium of five world-class colleges integrate amazingly well.  A natural stopping point between Boston and the Berkshires, Northampton is the perfect hub for a night away during a Massachusetts foliage cruise. Save room in the backseat for your haul from the region’s legendary antiquing shops, too. 

Camden, Maine
 The beautiful harbor of Camden, ME. Photo by Amy Bouchard @thetipsynewenglander

Newport, RI
There’s just no way around including Newport’s famous Ocean Drive on any New England road trip list; but we think it’s at its absolute best with fall hues edging the manicured gardens of these famous estates.  With no shortage of cafes, bistros, museums, galleries, and parks to break up your leaf peeping tour for a few hours, you may not want to leave Newport’s unique mix of historic charm and modern, urbane amenities.  Be sure to bring along our Red Coastal Clutch for a night out at Bowen's Wharf, and you'll fit right in with the nautical vibe!
Rockport, MA
A striking red building on Bradley Wharf in Rockport has been famously painted so many times that it’s now simply named Motif #1. The rest of Rockport feels just as much like a painting: a fleet of lobster boats, a long history of seamanship, fry shacks lining the streets, and classical New England views in every direction. Alongside Gloucester, the towns of Cape Ann peninsula are a scenic destination for coastal foliage perfection and bundled-up beach walks. 

Mystic Seaport, CT
Work your way south along Connecticut’s backroads towards the shoreline, taking in the wooded sights and autumn tones until that sea-spray air fills your lungs. At the mouth of the Mystic River, protected by a collection of islands and peninsulas, Mystic Seaport gives a glimpse into New England’s roots and a slower pace of life.  Those cool, crisp fall mornings sure help accentuate that sleepy sea-side vibe, too.  Despite the hustle and bustle of excellent restaurants and breweries, a walk along the waterfront and over the famous drawbridge offers a quiet retreat.  

Did we miss your favorite spot? Be sure to drop a comment below and let us know where you love to road trip in the fall!

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