An Under-the-Radar Island with Seafood and Solitude Lies Between the Mainland and Martha’s Vineyard

The beautiful Elizabeth Islands stretch along the southern side of Buzzards Bay like a string of pearls. The first European visitor, Englishman Bartholomew Gosnold, arrived way back in 1602, 18 years before the Mayflower landed in Plymouth. Today, the township area encompassing these islands bears his name, but most of the Elizabeth Islands are private quiet summer getaways. 

The only community where you can visit and stay is Cuttyhunk Island, situated about 14 miles south of New Bedford and 6 miles north of Martha’s Vineyard’s iconic island charm. But there’s a catch, as there are no roads to take you there; you can only arrive by boat, either your own or via the hour-long ferry ride from the mainland. The island sits at the confluence of three bodies of water: Rhode Island Sound, Vineyard Sound, and Buzzards Bay.

Fringed with gorgeous beaches facing Martha’s Vineyard and the surrounding waters, Cuttyhunk is a little slice of New England island life that feels secret and undiscovered. It’s not a place to visit if you’re looking for nightlife, varied shopping, or a wide selection of restaurant choices — although there are enough eatery options to keep you happy. Instead, it’s a tranquil getaway that few people know about and even fewer have explored, one of those exceptional experiences you can only have in Cape Cod.

Finding your way around the island is easy, not for a lack of things to do but because it’s a compact community built around the harbor. In total, the island measures about a mile and a half long and three-quarters of a mile wide. The island’s west side is a nature preserve with trails for hiking or bicycling. You can also find some hidden beaches and World War II bunkers. Nature lovers will enjoy strolling the sandy paths and beaches while taking in the sea views, and the island is a hotspot for birding during migrations.

Island life centers around the dock; if you head here looking for fresh seafood, this is where you’ll find it. The Cuttyhunk Cafe and the Lobster Shack, both island staples, are on the harbor. If oysters are your thing, check out the Raw Bar, just a few steps farther down the docks. The oysters come from Cuttyhunk Shellfish Farm on the island’s western side, so they couldn’t be any fresher. If you’re visiting by boat, the Raw Bar Boat will bring any item from their menu right to your mooring!

When you’ve filled up on delicious briny treats, it’s time to walk off a few calories. A 15-minute walk brings you to Lookout Hill, the highest point on the island. The site was used to keep watch for German subs during World War II. From there, you can see the entire island, the mainland, and the nearby islands of Martha’s Vineyard and Penikese, an area with its own interesting wildlife and beaches. Cuttyhunk’s beaches are also incredible, of course, and as you walk the island, keep an eye out for little shops where you can buy something to remember your trip by.