By Boat from the Harbor: Cuttyhunk, Quick's Hole, and the Elizabeth Islands

The Chain

The Elizabeth Islands run in a chain from northeast to southwest across the mouth of Buzzards Bay: Nonamesset, Uncatena, Naushon, Pasque, Nashawena, Cuttyhunk. The channels between them are called holes. Most of the islands are privately owned, visible from the water but closed to visitors. Cuttyhunk, at the southwestern end, is the exception. By private boat from Westport Point harbor, it's about twenty minutes on a calm morning.

Distances from Westport Harbor

Cuttyhunk: roughly 20 minutes. Gas dock now available at the town pier. The fishing on the backside is some of the best in southern New England.

Quick's Hole: roughly 30 minutes. The passage between Pasque and Nashawena. Forbes family islands on both sides. Watch the current.

Menemsha: 1 to 1.5 hours depending on conditions. Worth the run for the harbor alone.

Penikese: roughly 25 minutes. Bird sanctuary. No landing permitted.

Conditions matter. Buzzards Bay can build fast. Check the weather, check the tides, and respect the water.

Waterfront backyards with docks and boats on moorings at Westport Point

Wide angle showing the bridge, the Point, and open water beyond

Cuttyhunk

In 1602, Bartholomew Gosnold arrived aboard the bark Concord, looking for sassafras to trade. He established the first English settlement in New England, eighteen years before Plymouth. The settlement didn't last. The sassafras trade did. Today, Cuttyhunk has about ten year-round residents, no cars to speak of, and a quiet that makes Westport Point feel like a city.

The Cuttyhunk Fishing Club was founded in 1864. Presidents Theodore Roosevelt and William Howard Taft fished for striped bass from its shores. The club still operates. Breakfast on the porch of the Fishing Club, looking out at Buzzards Bay with coffee and eggs and no agenda, is one of those experiences that stays with you longer than it should.

At the Cuttyhunk dock with the CUTTYHUNK sign on the shingled building

Picnic table at the top of Cuttyhunk with harbor and ocean panorama below

Quick's Hole

Quick's Hole is the passage between Pasque and Nashawena islands. Both are Forbes family land, private since 1842, when John Murray Forbes made his fortune in the China trade and railroads and decided to buy a chain of islands. Scottish Highland cattle graze on the shores. Stone walls run across land that has no roads and no shops. Passing through Quick's Hole by boat, you're looking at a different century. The Forbes family has kept it that way deliberately.

Menemsha

Menemsha Harbor sits on the western tip of Martha's Vineyard. It's a separate run from Westport, not part of the Elizabeth Islands chain. A working fishing village with shingled shacks and weathered docks. The sunset from Menemsha Beach is famous enough that people applaud when the sun goes down. From Westport Point, it's a longer trip than Cuttyhunk but worth the run.

Penikese

Penikese Island is where Louis Agassiz, the naturalist, founded a school of natural history in the 1870s. Students came to study marine life in the field, not from textbooks. The school is gone. The island is now a bird sanctuary, visible from the water, off-limits on land. The terns don't seem to mind.

Pulling into the dock at golden hour, village behind

Looking back from the boat, wake behind, open water, sunset

Family heading out by boat from Westport Point harbor

Getting There

Cuttyhunk is accessible by ferry from New Bedford. The Cuttyhunk Ferry runs seasonally and is the easiest way to visit without your own boat. If you are arriving by boat, Cuttyhunk harbor now has a gas dock, a relatively recent addition that longtime visitors will appreciate. For years there was no fuel available on the island.

From 2042 Main Road, you're watching these islands from the harbor. But we're not running a charter service. If you're bringing your own boat, there may be dock space available at the property ($4 per foot per night, ask ahead). If you're not, the ferry from New Bedford is your best bet for a Cuttyhunk day trip. Either way, it's worth the trip.

Geography Matters

These are separate runs, not one continuous route. Cuttyhunk is the westernmost Elizabeth Island. Quick's Hole is further east between Pasque and Nashawena. Menemsha is a separate trip entirely, heading toward the Vineyard. Plan accordingly, check the weather, and respect the water. The harbor at Westport Point has been sending boats to these islands for centuries. The runs haven't changed. The tides haven't changed. Only the reasons have.

Westport Harbor and approaches. The Knubble guards the eastern entrance. Gooseberry Island and Hens and Chickens reef to the south.

The Elizabeth Islands from Westport Harbor. Cuttyhunk is the closest, roughly 8 nautical miles. Menemsha on Martha's Vineyard is about 24 nautical miles via Quick's Hole.

From Westport Harbor

Cuttyhunk: 8 nm, roughly 20 minutes. Gas dock at the town pier. The fishing on the backside is some of the best in southern New England.

Penikese: 7 nm, roughly 25 minutes. Bird sanctuary. No landing permitted.

Quick's Hole: 12 nm, roughly 30 minutes. The passage between Nashawena and Pasque. Watch the current.

Menemsha (Martha's Vineyard): 24 nm, 1 to 1.5 hours via Quick's Hole.