Pumpkin spice and covered bridges: 9 stops on a family-friendly fall road trip in New England

Travel from Boston to Bar Harbor and beyond on this scenic, family-friendly adventure

Freedom Trail graveyard. | Photo: Amanda Adler

Leaf peepers flock to New England each fall to take in the region’s stunning foliage, pleasingly cool temps, and fresh-from-harvest cuisine. While young couples and retirees check into quaint bed-and-breakfasts, settle down to savor fresh seafood, and sip on locally crafted beers and wine, fall marks an equally compelling time to take the entire family on a road trip through this area, which is bursting with active adventures for all ages.

Related Everything you need to know about fall road trips

a metal marker on the ground for boston's freedom trail
Freedom Trail. | Photo: Amanda Adler

1. Freedom Trail

There’s no better place to kick off a journey through New England than at one of the most storied cities in the U.S.—Boston, Massachusetts. Bring the classroom to life as you explore the area’s many historic landmarks on foot by following the 2.5-mile Freedom Trail

This red-brick journey meanders past 17 significant sites, many of which are free to enter, as you walk in the footsteps of the nation’s forefathers. Discover graveyards, see Paul Revere’s house, lounge in Boston Common, and grab a tasty bite to eat at Faneuil Hall before hitting the road for even more adventures.

a wand shop with stacks of thin cardboard boxes on shelves and a clock
Wynotts Wands. | Photo: Amanda Adler

2. Wynott’s Wands

Next, head for Salem, Massachusetts, a town with an infamously eerie backstory. Spooky season is the prime time to visit this legendary locale, as you step into one of the many museums that explore the town’s witchy past, and indulge in a ghost tour to learn about the lore that surrounds many of the buildings still standing today. 

Related Real-life locations where you can live out your Wizarding World fantasies

Your young readers will no doubt want to head to Wynott’s Wands, where they can gear up with their very own magical accessories. Here you’ll find floor-to-ceiling shelves stocked with wands of every shape and size, along with other playful Wizarding World-themed gifts, and more than a few nods to famous witches and wizards from the Harry Potter franchise. 

a sea port in new england with boats and waterfront structures
Kennebunkport. | Photo: Amanda Adler

3. Kennebunkport, Maine

Head up the Atlantic seaboard, making time to stroll through the picturesque waterfront towns, before stopping to enjoy a few nights in the quintessential New England hamlet of Kennebunkport, Maine. 

Related Top 10 things to do in Maine

Here you can hop aboard a trolley, browse shops that look like they’re straight out of a Hallmark movie, and catch a glimpse of whales heading south for winter. In early fall, you can camp or glamp at a secluded beach forest at Sandy Pines Campground, which offers unique family-friendly accommodations and amenities.

a white lighthouse on a rocky outcropping over blue water under blue skies
Portland Head Lighthouse. | Photo: Amanda Adler

4. Portland Head Lighthouse

Heading farther up the Maine coast you’ll find lots of lookouts begging to be explored. While there’s no shortage of landmarks along your route, the Portland Head Lighthouse is a scenic stop the whole family will enjoy. 

Little legs will find plenty of room to roam here alongside crashing waves and the oldest lighthouse in Maine. It’s an iconic scene, and as you investigate, you’ll uncover unique rock formations that resemble petrified wood. Stroll along the area’s walking trails and pack a picnic to take in the surrounding beauty.

rows of colorful donuts in a bakery case
Holy Donut. | Photo: Amanda Adler

5. The Holy Donut

Portland, Maine, is a foodie wonderland, with menu items like iconic lobster rolls and decadent duck fat fries offering satisfaction for your tastebuds. But the city’s longest lines are often found at a donut shop. 

The Holy Donut has three locations boasting gourmet pastries that come in flavors ranging from cinnamon sugar and pumpkin spice to chocolate coconut, honey lavender, and sweet potato ginger. But what really makes these confections unique is their recipe, which uses riced potatoes to give the donuts a flavor, texture, and consistency that’s unlike anything you’ll find at your local bakery. 

a boy sits on a rock and looks out at a scenic overlook of greenery
Acadia National Park. | Photo: Amanda Adler

6. Acadia National Park

Acadia National Park is brimming with mountains, beaches, wetlands, forests, lakes, and other natural wonders unique to this outdoorsy paradise. Epic sunrise views—and magnificent leaf peeping—can be found atop Cadillac Mountain; the park’s tide pools offer the chance to explore an ecosystem that’s often underwater; and the coastal downtown of Bar Harbor, Maine, provides endless opportunities to sample the region’s bountiful seafood, along with other tasty treats. Head for Jordan Pond to grab a popover, a soufflé-like roll that’s sure to keep everyone’s hunger at bay.

a blue and yellow train on a mountaintop under heavy gray clouds
Mount Washington Cog Train. | Photo: Amanda Adler

7. Mount Washington Cog Railway

Heading east into the colorful White Mountains of New Hampshire you’ll spy Mount Washington, the highest peak in the Northeastern U.S. The drive up the mountain is a harrowing experience, full of steep drops and nail-biting blind turns. 

Related Searching for New Hampshire’s most weatherproof cat at the Mount Washington Observatory

A more peaceful journey upwards can be found aboard the Mount Washington Cog Railway. It’s the world’s first mountain-climbing cog railway, where visitors choose between a steam or biodiesel-powered locomotive. Upon summiting you’ll be treated to impressive views, and likely strong winds. Be sure to pack layers and plan for chilly weather.

a waterfall cuts through a rocky gorge with wooden walkways surrounded by greenery
Kancamagus Highway. | Photo: Amanda Adler

8. Kancamagus Highway

Though there are many breathtaking roadways to enjoy throughout fall in New England, the 34.5-mile drive along the Kancamagus Highway is one of the most spectacular. You’ll want to allocate a full day to this deceptively short stretch of your road trip, leaving ample time to wander along the many hiking trails. Take in waterfalls, covered bridges, and mountain overlooks offering panoramic views of leaves ablaze with red, orange, and yellow shades. Pack your fishing poles and hunt for trout in the Swift River or in the ponds and streams along the route.

a waterfall cuts through a gorge with a wooden walkway surrounded by green rocks
Flume Gorge. | Photo: Amanda Adler

9. Flume Gorge

When it comes to epic outdoor adventures, the Flume Gorge in Franconia Notch State Park makes the perfect pit stop to close out your fall family getaway. Explore this natural chasm by following a self-guided 2-mile trail. You’ll trek uphill (and up a fair number of stairs) for some of the path, so you’ll want to come prepared. Gear up in suitable footwear before embarking on this rewarding journey that offers a doable challenge for the novice hikers in your group. Look out for the Wolf’s Den cave, which is the perfect size for kids to crawl through. The attraction closes for the winter, but the state park is open year-round.