This isolated outpost at the southern end of the Elizabeth Islands chain beckons boaters like a modern-day Shangri la. Indeed, the very name evokes mystery.
Long used by Wampanoags as a seasonal fishing and hunting grounds, Cuttyhunk was visited by English explorer Bartholomew Gosnold in 1602. In 1693, after changing hands several times, the 580-acre island was purchased by Peleg Slocum, a Quaker preacher and merchant from Dartmouth, on the western shore of Buzzards Bay.
Many members of the Slocum family lived on the island, which they owned for the next 200 years, leasing much of the land to tenant sheep farmers. Some early residents of Cuttyhunk were also known as “wreckers” who would salvage ships and their cargo after the vessels foundered on the rocky reefs near the island. Still others were hired as pilots to guide merchant vessels into Buzzards Bay ports.
Prior to 1864, Cuttyhunk belonged to the Martha’s Vineyard town of Chilmark, until John Murray Forbes, a wealthy Bostonian whose descendants still own the remainder of the Elizabeth Islands, helped transfer ownership to the newly established town of Gosnold, allowing Cuttyhunk to become independent.
In 1870, an elite fishing club for wealthy urbanites was built on the island’s southeast shore. These anglers, equipped with thumb-stall reels and perched upon spindly stands extending seaward, would haul in huge stripers and bluefish from the foaming waters of Vineyard Sound. The Cuttyhunk Fishing Club closed in 1921 due to a decline in the striper population, but the clubhouse still exists as a bed-and-breakfast. Oh, and the fishing is again fantastic.
Today, Cuttyhunk serves an idyllic retreat for recreational boaters, who can grab a mooring or slip inside the protected harbor and go ashore to explore the small village or the lovely beaches. The island is within reach of many southern Cape Cod and Buzzards Bay launching spots (South Dartmouth and Falmouth Harbor are 9 and 16 nautical miles distant, respectively). Duck inside the peaceful, protected harbor and call on Cuttyhunk Marina, at the town wharf, to see about short-term dockage. For moorings ($35/night), contact Jenkins Moorings or Frog Pond Marine.
Once ashore you can wander the hilly slopes for amazing views of Vineyard Sound and Buzzards Bay, play in the surf at Barges Beach (named for a series of rock-filled barges that were installed to prevent erosion), grab a hot dog at Bart’s Cart or cast a plug for stripers or bluefish in one of the greatest surfcasting venues in the world. If you choose to spend the night, be sure to hail Cuttyhunk Shellfish Farms, which will deliver ocean-fresh oysters and other raw-bar items direct to your boat.
The tiny village is home to a few gift and clothing shops, a pizza shop, a snack cart and a grocery store, but other than that there isn’t a whole lot to buy on the island. And for many that’s a good thing. If you’re interested in the island’s history, pay a visit to the Cuttyhunk Historical Society’s small museum. Here you’ll also find a map of walking trails leading to the southwestern side of the island. Bird life abounds in the thickets and scrub oak, and the views are amazing. In fact, you may find yourself looking for whaleships on the horizon.