Sailing New England – Magical Cuttyhunk

Cutthyhunk main dock and boats

Sailing New England – Magical Cuttyhunk

Have just returned from a glorious week sailing around New England (or part of it anyway). This trip was on my wish list for a long time, and it was definitely worth the wait. 9 friends, 7 days, 5 moorings, 2 sailboats…idyllic doesn’t begin to describe it. It was a voyage of discovery for me – I was seeking the fabled New England seaside charm I’d always seen in books and movies. Luckily, I found that – plus lots of other unexpected pleasures. One of them was Cuttyhunk.

To start our adventure, we picked up our boats in Newport from Bareboat Sailing Charters – a Jeanneau 49 DS and a Jeanneau 439 (with a beautiful blue hull – I LOVE a blue hull). After a whirlwind provisioning run to Stop ‘n Shop and Harry’s Package Store (every sailing trip requires rum!) we spent a night on the mooring so that we could head out early the next day. By 8am we were on our way to Cuttyhunk. It was a gorgeous sail of about 20nm with a steady downwind breeze, building as we went. It’s a good thing we got there early; all of the slips and moorings at the Cuttyhunk Town Marina were taken, but we grabbed 2 of the last moorings in the outer harbor.

Aerial view of Cuttyhunk island

Aerial view of Cutthyunk Island. Photo credit

Cuttyhunk is a pretty magical place. Just shy of a square mile in area, it has about 400 summer inhabitants, but a year-round population of less than 50 hardy souls. It’s the easternmost of the Elizabeth Islands and was discovered in 1602. The only way to get there is by ferry from New Bedford, MA, private boat, or seaplane. From the 1860s to the early 1900s, the island attracted financiers, oil tycoons and presidents who came to fish the area’s legendary striped bass at the Cuttyhunk Fishing Club.  Today, the Fishing Club is a small B&B, and the island is a sleepy village that comes alive (a relative term) during the summer.

Cuttyhunk market and deli

Cuttyhunk’s only market and deli.

The beauty of Cuttyhunk is that there is nothing to do. And that’s a good thing. There are just a handful of cars on the island, plus a church, post office, and one room schoolhouse (which currently enrolls 2 students). There’s one proper restaurant and a small market and deli, plus an excellent ice cream shack – I can highly recommend the homemade ice cream sandwiches. There are no bars – the island is dry (so BYOB!). The Fish Dock, located in the sheltered inner harbor, is the center of activity for visitors and islanders alike. Fresh local seafood is available for take-away from the fisherman on the dock. Or you can hail Cuttyhunk Shellfish Farm‘s infamous “Harbor Raw Bar” on VHF channel 72, and have fresh Cuttyhunk oysters, clams, shrimp, chowder, and other specialties delivered right to your boat. How cool is that?

Because there are few cars, the island is a lovely kind of quiet, where you mostly hear the wind blowing, insects chirping and the sea murmuring. The island is hilly and rocky, covered with scrubby grasses, honeysuckle and wild beach roses. If you follow the one main road all the way to the top, you come to Lookout Hill; at 154 feet above sea level, there is a stunning 360-degree vista of the island, Vineyard Sound, Buzzard’s Bay, the mainland, Martha’s Vineyard and the Elizabeth Islands. During World War II, soldiers were stationed on Lookout Hill to watch for Nazi submarines. Today the former Army and Coast Guard bunker is a picnic area with sweeping views of the windswept island with its clapboard houses surrounded by pink and blue hydrangea, rocky hillsides, and beyond that, the ocean.

Hiking to Lookout Hill on Cuttyhunk

Hiking to Lookout Hill on Cuttyhunk


Cuttyhunk view from Lookout Hill

View over the harbor from Lookout Hill on Cuttyhunk


striped bass weathervane on top of Cuttyhunk church

Striped bass weathervane atop Cuttyhunk’s only church. Photo credit:


There are a couple of beaches – the first one you see coming into Cuttyhunk is Channel Beach, where folks pull up their dinghies and settle in around a campfire in the evenings. There’s also Barges Beach, and Church’s Beach looking out over Buzzard’s Bay. Fully half of the island is set aside as a nature preserve. The west end of the island has winding trails for hiking that lead to West End Pond, where local oysters are cultivated. There are 100 or so houses scattered around the island, many down meandering private paths. For the most part, the houses are modest – no Newport or Hamptons style mansions here. They would feel out of place, anyway.




A typical house on Cuttyhunk with sea view and hydrangea

Typical house on Cuttyhunk, with hydrangea border and sweeping sea view.

You can walk everywhere on Cuttyhunk, and you should. Some residents use golf carts to get around town, but for the most part people walk. Or more accurately, they amble. When there’s nothing to do and nowhere to go, people more more slowly, and have time to take in the natural beauty of the land and seascape. Cuttyhunk feels apart from everything – a bit frozen in time, and worlds away from the hustle of the mainland.

After only a day here, I was charmed by the island’s natural beauty and refreshed by the quiet and solitude. I can’t wait to go back – and do nothing, again.


rocky beach on Cuttyhunk

A rocky beach on Cuttyhunk. Photo credit: