Hit the Road this Fall for the Ultimate New England Road Trip

Sunrise at Hampton Inn by Hilton Bar Harbor
Hampton Inn by Hilton Bar Harbor

When it comes to seeking out ideal leaf-peeping spots this fall, you’re guaranteed to find enchanting scenery in New England. The area’s winding mountain roads, captivating coastal towns and bounty of natural wonders make it the perfect getaway locale for autumn road trippers.

So pack your cardigans and boots and chart a course for adventure as you journey along scenic streets on this ultimate New England itinerary.

Savor Seaside Charm in Newport, Rhode Island

Castle Hill Lighthouse Newport, Rhode Island Sunset New England Fall
Castle Hill Lighthouse Newport, Rhode Island - Photo Credit: P Meybruck/Shutterstock

When dreaming of autumn in New England you’re likely picturing colorful trees, ocean breezes and quaint downtown areas full of cafes and colorful storefronts. In Newport, you’ll find all this and more. Boasting everything from mansion tours and cultural museums to a coastal cliff walk and rail bike excursions, this effervescent enclave is overflowing with activities to enjoy. Take a trolley tour around town, cruise the 10-mile Ocean Drive and slip into an Adirondack chair as you sip your way through a tasting flight at a local winery before turning in at Homewood Suites by Hilton Newport Middletown, RI, situated on Aquidneck Island.

Walk Through History in Boston, Massachusetts

Boston, Massachusetts Skyline. New England Fall
Boston, Massachusetts - Photo Credit: Sean Pavone/Shutterstock

Next, hit the road and head east to take in the sights of one of America’s earliest settlements, Boston. Steeped in history, this bustling harbor town is the perfect setting for a fall stroll through charming parks and squares. Walk the legendary Freedom Trail, stopping to appreciate its many historic sites and museums, reflect on the past as you explore ancient cemeteries, take in the fresh autumn air in Boston Common and dine at America’s oldest restaurant. Shop for wares amongst the many stalls at Faneuil Hall then settle into a room at the centrally located Hilton Boston Downtown/Faneuil Hall.

Drive New Hampshire’s Scenic Kancamagus Highway

Kancamagus Highway, New Hampshire, New England Fall
Kancamagus Highway, New Hampshire – Photo Credit: YuziS/Shutterstock

Heading north into the White Mountains of New Hampshire, make your way to one of the region’s best spots for enjoying fall foliage as you enjoy a drive along the iconic Kancamagus Highway. This 34.5-mile stretch of road offers magnificent views without ever leaving your car, but you’ll also want to stop along the way to embark on stunning hikes to waterfalls, gorges, covered bridges, mountain overlooks and more. After a breathtaking drive or train ride up to Mount Washington, settle in for the night at Home2 Suites by Hilton North Conway, which is nestled beside many exciting attractions.

Enjoy National Park Adventures in Bar Harbor, Maine

Acadia National Park Maine Fall Foliage New England Fall
Acadia National Park - Photo Credit: Skyler Ewing/Shutterstock

As you steer eastward into Maine, be on the lookout for the many moose who call this state home. Make the charming town of Bar Harbor your next destination, where you can explore the many natural wonders of Acadia National Park. Take an easy stroll along coastal paths or set out for challenging hikes to mountain summits, then take off on a whale-watching expedition before enjoying an evening spent exploring the area’s many shops and restaurants. Hampton Inn by Hilton Bar Harbor is the ideal home base for your adventure, and you’ll want to stay for several nights to enjoy it all.

Taste Your Way Through Coastal Maine Cuisine

Portland Head Light Lighthouse Fall Foliage Maine New England Fall
Portland Head Light – Photo Credit: Danita Delimont/Shutterstock

Lobster rolls, chowder, clam bakes and oysters await as you snake your way along the Maine coastline. Allow plenty of time to enjoy the many idyllic seaside towns, local breweries, picture-perfect lighthouses and all the freshly caught seafood your heart desires as you make your way to Maine’s largest city, Portland. Continue your culinary pursuits by tasting other popular regional eats such as Duckfat frites and sweet treats from The Holy Donut before toasting farewell to your unforgettable adventure over craft cocktails and port views at the rooftop bar at the chic Canopy by Hilton Portland Waterfront.

Looking for more fall adventures? Get a true taste of fall at these foodie fests.