7 Islands in the Northeast That Are Worth a Visit
Islands are probably not what come to mind when you think of a trip to New England, but they should be. These spots are all accessible through ferries and tour operators and will show you a side of the Northeast that few think to explore.
Heading out the door? Read this article on the new Outside+ app available now on iOS devices for members! Download the app.
No yacht? No problem. Sure, the Maine coastline alone has some 3,000 islands you can’t set foot on without a watercraft and some navigation skills, but many of New England’s best offshore adventures are found on islands that you can buy a ticket to.
Word to the wise, though: New England’s islanders brook no foolishness. They welcome visitors into their communities but prefer outsiders stay off their lawns, thanks. Island towns aren’t theme parks, and this summer of all summers, island-hoppers would do well to respect the communities that host them. Follow distancing and face-mask guidelines. Don’t assume you can buy anything you need in an island town. Don’t take pictures of the locals, avoid mentioning Tom Brady, and learn the friggin’ ferry schedule, bub.
The hour-long ride on the Monhegan Boat Line from the fishing village of Port Clyde is itself worth the trip: you’ll see spruce-studded isles, seals lounging on ledges, porpoises playing in the boat’s wake, and the occasional prehistoric-looking sunfish hovering just beneath the surf. Other Monhegan ferries run out of New Harbor and Boothbay Harbor.
You can see a lot of Monhegan on a day trip, but the quiet rhythm of the island community, with its year-round population of about 70 and summer population of a couple hundred, is better appreciated with an overnight at one of a handful of inns and rentals. The Island Inn, which delayed its opening until June 22 this year, is the most quintessential, with its weathered-shingle exterior, airy rooms, and restaurant overlooking the harbor. Visit the Fish House for lobster rolls you can eat outside by the town’s pocket beach. A dozen miles of hiking trails wend through woods and over seaside cliffs; trails on the island’s east end, farthest from town, are the most magnificent, looking out from the headlands over endless ocean. Along the short Lobster Cove Trail, hikers pass the remains of the D.T. Sheridan, a coal-towing tug that ran against rocks in a dense fog in 1948. Not far from the wreck site, the Monhegan Brewing Company’s beer garden is delimited by stacks of old lobster traps, and after happy hour you can browse Monhegan’s dozen open art studios while you wait for the return boat.
Boston Harbor Islands, Massachusetts
While the preppy and deep-pocketed prefer to retreat to Martha’s Vineyard and Nantucket, Boston Harbor’s eight ferry-accessible isles are a wilder and less commercial summer-island alternative. Cooperatively managed by the state of Massachusetts, the National Park Service, and other agencies, Boston Harbor Islands National and State Park offers hiking trails over low drumlin hills, as on Spectacle and Long islands, mudflats and salt marshes that attract birders to Grape and Peddocks islands, and explorable remnants of old military forts on islands like Lovells and Georges. Ferries come and go from Boston (this summer’s schedule is still TBD) and, on the south side of the bay, Hingham. Dress code does not include popped collars or salmon-colored shorts.
Frenchboro Long Island, Maine
Maine’s largest and most visited island, Mount Desert Island, is home to the lion’s share of Acadia National Park and welcomes millions of summer visitors. But just south of MDI, Frenchboro Long Island offers similar scenery and comparative solitude. From Bass Harbor, on MDI’s southwestern edge, the state ferry reaches Frenchboro, with its one-room schoolhouse, cluster of homes around the harbor, and spectacular Frenchboro Preserve, protected and stewarded by the Maine Coast Heritage Trust. Fridays are the only time to visit this summer, on account of a reduced ferry schedule, but the draw is 14 miles of some of New England’s finest coastal trails, leading hikers to remote coves and oceanside bluffs where bald eagles circle overhead. Come prepared with food, water, and gear, as there’s no store on the island—just Lunt’s Dockside Deli, a must-stop for blueberry pie and lobster coming on or off the ferry.
Isles of Shoals, New Hampshire
In a normal summer, ferries serve a hotel on Star Island, on the New Hampshire side of this archipelago straddling the Granite State’s border with Maine. They’re canceled this year, as are boat trips run by the Shoals Marine Laboratory, a field station and education center on the Maine side that usually offers walking tours of Appledore Island’s gardens and gnarly rock formations. You can still explore the isles, though, on a guided kayak tour with Plum Island Kayak, in Newburyport, Massachusetts. The outfitter brings paddlers, boats, and gear out on a cabin cruiser for full-day paddles that take in seabird colonies, sunning seals, and a century-old lighthouse.
The Fox Islands, Maine
The populations of North Haven and Vinalhaven, in Penobscot Bay, swell in the summer. Both are accessed via ferry from Rockland, a onetime cannery town that’s now a food and art hot spot. North Haven has a pastoral appeal, with quiet pebbly beaches and a minimalist town center. The culinary scene is almost entirely contained in one building, Calderwood Hall, which has a pizza café upstairs and a brewery downstairs. The other dining option, at Nebo Lodge, is a tablecloths and reservations kind of place—Maine crab gazpacho, filet mignon—with a bar that’s a great spot to slurp bivalves from North Haven Oyster Company. Across the channel, called the Fox Islands Thoroughfare, Vinalhaven has a town center with a dozen or so spots to eat and drink: a seafood shack, a coffee shop, a bar, and fine dining. The best way to get around either island is on a bike—in the busy months, the ferries have limited room for cars, and the quiet island roads are a joy to pedal. No ferry connects the islands, but cyclists can cover the eight miles between downtown Vinalhaven and the thoroughfare, then use a dock phone to call Brown’s Boat Yard on the North Haven side for a shuttle across ($5 per person, $2 per bike). You can stay the night on either island, or catch the last ferry back to Rockland for a nightcap.
Cuttyhunk Island, Massachusetts
A slender island chain off Cape Cod separates Buzzards Bay from Vineyard Sound, and the last isle in the row is scrubby, windswept little Cuttyhunk, serviced by a ferry out of New Bedford, Massachusetts. A couple of B&Bs rent rooms: Avalon and Cuttyhunk Fishing Club, the latter nodding to Cuttyunk’s chief draw for many visitors—primo striped-bass fishing. The other big draw is peace and quiet, with visitors strolling the rutted dirt roads (there are next to no cars) and lounging on beaches. Eats are mostly al fresco: there’s Isla Tacos, a dockside taco and churro stand, and Soprano’s, where pizzas are cooked in a garage and served at picnic tables in the driveway. But the most particular attractions are the oysters raised offshore. Cuttyhunk Shellfish Farms’ floating raw bar makes briny deliveries to boats in the harbor, while its shack on the wharf serves oysters shucked to order, optionally accompanied by a cup of hot chowder.
The Casco Bay Islands, Maine
Most travelers visit Portland for its deservedly buzzy food and drink scene and its cobblestone Victorian vibe, but the city is also a jumping-off point for the more bucolic charms of the Casco Bay islands, six of which are serviced year-round via short ferry rides from Portland’s Old Port District. Highlights include Peaks Island, essentially a Portland bedroom community (you’ll share the 20-minute ferry ride with commuters) that has rocky beaches, beaver ponds, and a few miles of wooded trails on its western side, away from the ferry dock. Also on Peaks’s “backshore” is Battery Steele, a catacomb-like World War II military fort full of murals and graffiti and open for exploring. Chebeague Island has sandy beaches and an elegant Gatsby-era inn with an inviting porch for cocktail hour. At low tide, the adventurous can cross a sandbar to find a mile or so of wooded trails and some beachside campsites on uninhabited Little Chebeague. Great Diamond Island is a bit of a culinary destination: old-school Diamond’s Edge Restaurant serves steamed lobster and roasted halibut, while new-school Crown Jewel has crab corn fritters with gorgonzola mousse and baked oysters with yuzu pearls and pickled mustard seed (with a side of ironic Jimmy Buffet decor). Only Peaks has a regularly scheduled car ferry, but bring a bike on any passenger ferry for an extra $6.50—it’s the best way to get around any Casco Bay island.
This story was produced in partnership with Down East magazine.