Town of 200 Islands

Harpswell’s cribstone bridge spans the gap between Orr’s and Bailey Islands. Composed of stacked granite blocks that allow strong tides and currents to pass freely through, the bridge is reportedly the only one of its kind in the world.
The Aucocisco III pulls up at the dock at Cook’s Lobster and Ale House on Bailey Island. The Portland-based ferry offers seasonal cruises to Harpswell that leave the city at 10 a.m. and return at 3:45 p.m.
Yellow flowers festoon an old island home.
Morse’s Cribstone Grill on Bailey Island offers Maine classics like lobster (just about any way) and blueberry pie.
Harpswell is home to countless coves, where families carve out time to spend an afternoon by the water.
A classic cove view includes elements of work and play: lobster traps and pleasure craft.
Glen’s Lobsters, tucked inside Mackerel Cove on Bailey Island, sells lobster to the public.
The circa-1840 barn at Live Well Farm on Harpswell Neck makes a cozy wedding venue.
Guests can dock their boats at the Dolphin Marina and Restaurant while they have a meal.
A vintage car has a stunning parking spot.
Mackerel Cove has a narrow sandy beach and open grassy area at its head, known as Johnson Field Preserve.
Open ocean views are rare in Harpswell. More often, you will see land on the other side of an inlet.

With more shoreline than any other town in Maine, Harpswell lures visitors and inspires deep ties

Harpswell is Maine’s coast at its most ragged. The mainland, known as Harpswell Neck, is a 10-mile-long thread of a peninsula extending into Casco Bay. To the east of the Neck are a series of long, similarly narrow islands called Sebascodegan (known locally as “Great Island”), Orr’s, and Bailey Islands, linked by bridges and running more or less parallel to the mainland. Beyond these larger islands are nearly 200 others, some inhabited, others conserved and open to the public. The town has more coastline than any other in the state -216 miles -making the ocean inescapable. If you can’t see it, turn around. Take a deep breath of briny air and peer through the trees.

For centuries, fishermen have made their living on the ocean in Harpswell, and artists and craftsmen have been inspired to create here. Since the early twentieth century, people from East Coast cities have been summering here or staying for days or weeks at a time in waterside motels and inns. More recently, retirees and commuters have made their homes in Harpswell, which, despite its faraway feel, is only 20 minutes or so from Brunswick and less than an hour from Portland.

“For visitors to Maine, Harpswell is one of the first authentic working waterfront communities they encounter on their way up the East Coast,” says local real estate agent Kristina York, who grew up on Bailey Island. That word, ‘authentic,” has weakened by overuse, and yet it’s hard to talk about Harpswell without letting it slip. Like so many coastal Maine towns to the east, it is a study in opposites: simultaneously quaint and sophisticated, working-class and wealthy. At local restaurants, the bars are lined with people from every economic background, and moored in the harbors you’ll find an equally wide variety of boats. Brett Johnson of Maine Street Design Co. in Portland refers to his hometown as “homespun,” which also fits. Signs in front of white-steepled churches advertise events like ice cream socials and pancake breakfasts; kids ride their bikes to general stores for red hot dogs; the lobster traps stacked up in backyards aren’t for decoration.

Johnson is a 17th-generation Harpswell native. Although he grew up on Orr’s Island and now lives in Yarmouth, most of his extended family was—and still is—on Bailey, and he and his siblings own a home there. “For people who grew up here, Harpswell is made up of a collection of villages,” he says. On Harpswell Neck, the villages of Harpswell Center, West Harpswell, and South Harpswell are linked by winding rural roads. Despite the fact that “The Islands,” as Sebascodegan, Orr’s, and Bailey are called, have been connected by bridges for decades, they retain their own identities, and people make a point of telling you which one they’re from. Before the Ewing Narrows Bridge joined the mainland to the islands, those traveling by car had to drive through Brunswick to get from one part of Harpswell to the other, and there is a friendly rivalry between the two “sides,” each of which is home to a few beloved seafood restaurants, including Dolphin Marina and Restaurant on the southern tip of the Neck and Morse’s Cribstone Grill on Bailey Island.

For better and for worse, the Islands see more summertime tourists than the mainland. Travel guides lure visitors to cross the famous granite cribstone bridge (reportedly the only one in the world) between Orr’s and Bailey  and to shop at Land’s End, a picturesque Maine-themed gift emporium overlooking Casco Bay. Another Bailey Island landmark, Cook’s Lobster and Ale House, was in danger of closing before Jennifer and Nick Charboneau bought the restaurant in June of 2015. The day they reopened it, locals bombarded them with thank-you cards and gifts and offers to look after their children and dog. In preparation for the Fourth of July music and fireworks celebration held at Cook’s, a woman the couple hardly knew scribbled her phone number onto a piece of paper and pressed it into Jen’s hand, telling her to call if she got overwhelmed and needed someone to help wash dishes.

“People just like each other out here,” says Nick. Johnson—who has washed dishes at Cook’s himself to help the Charboneaus out—concurs, giving as examples the annual fundraiser held every winter to buy heating oil for low- income families and how many of the stalwart town leaders volunteer at the local fire department. “There’s a lot of quiet taking care of each other,” he says.

With so many islands and narrow, labyrinthine roads branching off Harpswell’s main drags, it is impossible to know every nook and cranny of its jagged coastline. Despite having grown up in Harpswell, Johnson is continually surprised at the miles of trail systems leading in and around fields, forests, marshes, and mud flats, and—because it’s worth saying twice—the 216 miles of shoreline. Johnson’s favorite place on Bailey Island is the Giant’s Stairs, an epic rock formation on the ocean’s edge. “I don’t think anyone should step foot in the town of Harpswell and not go there,” he says. “It’s one of my most sacred places.”

As the northernmost town in Cumberland County, Harpswell forms the end of Casco Bay and the start of the midcoast, making the town an island (or series of them) unto itself. “You get to Brunswick and you have a choice,” says Johnson. “You can keep going down Route 1 or you can make a turn toward Harpswell.” If you haven’t already, hit your blinker (or hop on the ferry) and explore the town for yourself.