There are some pretty famous islands in Massachusetts, but this isn’t about them. Cuttyhunk is a tiny little speck of an island at the mouth of Buzzards Bay, much less known than some of her more popular neighbors. Climb the hill, and you can get some good views of Gay Head Light on Martha’s Vineyard looking one way, and the mainland if you look off toward New Bedford. It lies at the end of the Elizabeth Islands, most of which are private.
But Cuttyhunk has a little fishing community, Gosnold, made up of a tiny year-round population. It also possesses a very nice harbor and just enough niceties to make it welcoming to cruising yachts. The only ferry service is a small afair, meaning it’s never really all that crowded.
This is the perfect sort of spot to experience a little taste of what life is really like on these islands. During the season, there are people around and things are open. During the shoulder season, it’s pretty darn quiet.
Exploring Cuttyhunk
If you’re looking for posh restaurants and lively nightlife, Cuttyhunk might not be your cup of tea. It’s a quiet island. The only real eating establishments are the Raw Bar, the Lobster Shack, and a little cafe, all located at the docks. The options are pretty limited. It is occasionally possible to get breakfast or maybe even dinner from one of the local “hotels,” the Fishing Club Inn. The Corner Store has gifts, and the IslandMarket and Deli has a few provisions.
Walking on Cuttyhunk is lovely, especially the long beach that faces the Vineyard. You can walk up the hill to the old military lookout post, and nature trails cross the lower two-thirds of the island. If you go off-roading here, however, be warned: the ticks are intense! Wandering the streets and beaches is fun, though.
Boating to Cuttyhunk Island
Entering the harbor looks worse on the chart than it really is. If you use the Aquamap app, the channel is surveyed for a stress-free entry. There are rocks and the typical hazards in the outer harbor area, so honor the marks and check your chart. This year, I came across a report of someone who hit a rock at high speed, causing significant damage to the keel of their very nice yacht.
If you want a slip or a mooring in the inner harbor, there’s only one game in town: Cuttyhunk Marina. There’s also a fuel dock just inside the harbor. Docks are available to be reserved on Dockwa, but moorings are first-come, first-served. Moorings in the harbor only accept vessels up to 50 feet long. There is some room for anchoring inside the harbor, but you must call the harbormaster to coordinate it.
There are also more moorings outside the harbor, both north and south of the channel. These are run by families on the island, and they’ll stop by and collect their money. The moorings to the south are run by the raw bar, which runs a boat around the harbor offering up fresh local oysters each evening. They’ll collect their mooring fee while also offering additional goodies.
Anchoring outside the harbor is challenging due to mixed holding conditions with lots of rock and weeds. There’s also a large portion charted as a cable area, although many boaters seem to ignore this (or are unaware and lucky). The area is completely exposed to all northerly quadrants, and watching the weather closely is recommended. Southeasterlies bring in a swell through the little inlet between Cuttyhunk and Nashawena.
Cuttyhunk Links and Resources
Walking Map courtesy Avalon Inn
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