New England is dotted with picturesque sites that look like they’ve been plucked straight out of a Hallmark movie—and a road trip through the region is arguably the best way to experience them. Whether you want to hop around the beaches of southern Maine or go leaf peeping in the mountains of Vermont, these charming small towns in New England will make you want to add a few more overnight stops to that road trip itinerary.
Bonus: Most (if not all) of these picks are year-round destinations, which means there’s really no “wrong” time to visit. What are you waiting for?
Concord is just one hour from Boston, making for a fun-filled day trip—and a history-filled one, as well. Not only did the first battle of the American Revolution take place here, but it’s also the former home of literary greats like Henry David Thoreau, Ralph Waldo Emerson, Louisa May Alcott, and Nathaniel Hawthorne.
Take a step back in time with a guided tour of Alcott’s Orchard House and a visit to famous Revolutionary War sites. Prefer to stay in the present? Walden Pond (which inspired Thoreau’s Walden) and downtown Concord (where shopping and dining options abound) are both worth a detour.
Middletown is an easy 10-minute drive from bustling Newport. Its most notable attractions include the 242-acre (98-hectare) Sachuest Point National Wildlife Refuge and the Norman Bird Sanctuary, which are popular spots for wildlife spotting and birding—book a guided hiking tour of both sites to learn more about the area’s native flora and fauna. Be sure to also carve out some time to visit one of Middletown’s beaches before feasting on fresh seafood—you are in the Ocean State, after all.
This vibrant riverfront destination is actually a former mill town, as evidenced by the abundance of old brick buildings that have been lovingly restored. Explore even more of Manchester’s hidden gems with family and friends via a fun-filled, self-guided scavenger hunt followed by a bite at a local eatery (its lively downtown area boasts 100-plus boutiques and restaurants).
Art and architecture enthusiasts also shouldn’t miss the Currier Museum of Art, which includes a collection of centuries-old European and American works, plus two Frank Lloyd Wright homes on the grounds.
Known as the gateway to Acadia National Park, beautiful Bar Harbor is best explored on foot. Gourmands can sign up for a culinary-themed walking tour or embark on a guided foraging excursion. Alternatively, history buffs can trek through town and marvel at old churches and theaters along the way.
Should you need a break from strolling, hop aboard a sailboat for a romantic sunset cruise. And don’t you dare skip town without popping into one of downtown’s colorful storefronts or indulging in some boat-to-table cuisine (fresh lobster, anyone?).
The tiny town of Mystic (population: 4,776) is the epitome of quintessential New England charm. Its downtown district is home to colonial-era homes, church steeples, and waterfront inns—not to mention a slew of shops and restaurants. Mystic Seaport, the largest maritime museum in the country, is arguably the destination’s most renowned attraction. But the Mystic Aquarium, where you’ll find the only beluga whales in New England, is a close second.
Stowe is best known for its top-rated skiing and snowboarding runs—but this town in northern Vermont is far from a one-season wonder. Whether you’re going for a day in the summer or a long fall weekend, expect plenty to see and do, be it hiking, mountain biking, or brewery hopping.
There’s also nothing wrong with strolling idly down Main Street, where charming buildings house mom-and-pop shops and cafés. This is where you’ll also find the famous 19th-century Stowe Community Church (and its equally famous steeple), often considered to be one of New England’s most photographed churches.
With its picturesque beaches and historic lighthouses, the coastal town of Kennebunkport is a must-visit—especially during the summertime. On sunny days, locals and travelers can be found relaxing at one of the nearby beaches or enjoying some kayaking excursions, catamaran cruises, and lobster tours.
Alternatively, if the weather’s not cooperating—or you simply need a break from the sun and the sand—you can visit famous sites such as the Seashore Trolley Museum, Goat Island Lighthouse, and Kennebunkport Historic District.