During the 19th century, Tarpaulin Cove, midway through Vineyard Sound on the south side of Naushon Island, was the most prominent port. It served as a refuge for cargo schooners seeking shelter on their New York-to-Boston course. Like many island harbors, Tarpaulin Cove lost the bulk of its business when the Cape Cod Canal opened in 1914.

In the mid-19th century, Naushon Island belonged to John M. Forbes, a close friend of Oliver Wendell Holmes, the leading literary light of Boston. In his "Autocrat at the Breakfast Table," Holmes rhapsodized about the beauty of Forbes's island estate:

In 1898, the four masted schooner, Lunet, loaded with coal, anchored here to wait out a Southwesterly gale. The next day, the winds changed direction to Northeasterly, and the hurricane force winds were accompanied by a blinding blizzard. Unable to escape, and now on a lee shore, Lunet was lost when her anchor parted and she sank in 60 feet of water with all 200 persons onboard. It was one of the worst disasters in New England shipping history.

Otherwise, in fair weather, Tarpaulin Cove is considered a lovely anchorage.

A fine place to anchor for the night on the east side of Naushon Island, especially when the southwesterly breeze is blowing. Before boats had motors, coastal schooners plying Vineyard Sound anchored here to await favorable tides.