During the shoulder seasons, Cuttyhunk boaters often have the inner harbor to themselves. Photos by Tom Richardson

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.

Live Zoomable Map
Getting There
Dockage, Moorings and Service
Boat and Kayak Rental
Things to Do and See
Where to Eat
Where to Stay
Ferry Service
Fishing Information
General Information

Cuttyhunk chart.

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.

SAT map.

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. 

A well-used skiff rests on the edge of Cuttyhunk Pond.

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.

The Corner Store carries cool clothing, gifts, beach stuff and more.

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.

Photo Gallery:

A kayaker makes his way through a peaceful Cuttyhunk Harbor.

Cuttyhunk as seen from Vineyard Sound.

Boaters can reprovision with basics at the Cuttyhunk Market.

Seals haul out on the rocks just east of the harbor entrance throughout the year.

The channel leading to Cuttyhunk harbor is well marked.

The island is home to boats of every size and style.

The Cuttyhunk Anglers Club once served as headquarters of an elite fishing club. Today it’s a comfortable B&B.

Cuttyhunk Pond is a scenic, sheltered spot, no matter what time of year you visit.

Cuttyhunk is famous for fishing, as evidenced by the rods you’ll see aboard the local boats.

The Cuttyhunk Ferry makes daily trips between the island and New Bedford in season.


Share this Article On Facebook Twitter More...


Like New England Boating on Facebook. Follow us on Twitter.
Receive our Daily News Update:

Don’t forget to sign up for our monthly newsletter!

Each month our emailed newsletter keeps you up to speed on the top news items, videos, destinations, reviews and fishing articles on New England Boating, so you won’t miss a beat. It’s convenient, it’s free, and you can opt out at any time!