Cuttyhunk

Fairhaven

Hadley Harbor

Marion

Onset

Padanaram

Quicks Hole

Red Brook

Tarpaulin Cove

Weekpecket Islands

Woods Hole

Buzzards Bay

Cuttyhunk

Visiting Cuttyhunk presents the classic paradox of travel to all remote and uncommercial places: how to appreciate them without undermining the very qualities you came to admire.

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Fairhaven

Fairhaven has at least two distinct faces, each of which contributes to its appeal as a cruising destination.

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Hadley Harbor

This perfect little gem of a harbor sits near the Buzzards Bay entrance to Woods Hole – at the nautical crossroads of southern New England.

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Marion

Marion offers a lovely, well-protected harbor and streets that are uniquely attractive among Massachusetts’ old coastal towns.

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Onset

The channel into Onset doesn’t feel as tight as the chart suggests, though, and at the end is a quiet, Victorian-inflected seaside resort.

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Padanaram

The harbor’s size, its quick access to Buzzards Bay, and the century-old tradition of the New Bedford Yacht Club station have made it a popular destination since yachting took hold here at the end of the 19th century.

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Quicks Hole

For a cruising sailor, Quicks is rarely on the way to anyplace except Menemsha, but it is a lovely and remote little stretch of water.

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Quissett

This legacy of slow development, punctuated by a significant grant of open space, leaves Quissett’s waterfront pleasantly sparse and unhurried.

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Red Brook

The harbor’s placid shorelines and quirky, down-the-rabbit-hole entrance make it worth a visit, especially if your schedule allows for time to get off the boat and explore the area by dinghy or on foot.

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Tarpaulin Cove

Nowadays the cove, like the rest of the island, is largely uninhabited, the lighthouse is automated and the (relatively) few boats transiting the Sound rarely need a sheltered anchorage to wait for wind or tide. Tarpaulin Cove is left mostly to daytime visitors.

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Weepecket Islands

If you’re passing by with time for lunch and a swim, or you need to get the kids ashore, stopping here can be the perfect answer.

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Woods Hole

Woods Hole is the Jekyll & Hyde of Massachusetts waterways — sometimes a placid and well-marked maritime thoroughfare, sometimes the most dramatic and dangerous mile of water on the coast.

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