Thomas Winsmore was an 1890 schooner that sailed in the coastwise trade, bringing coal from Philadelphia to northern ports, and returning with cargoes of lumber.

[1] A report from the United States Revenue Cutter Service describes one of the accidents that marked the end of 22 years of safe operation, when Thomas Winsmore went aground near Lookout Shoal, off the North Carolina coast:[5] The three-masted schooner Thomas Winsmore, on January 4, 1914, was in a predicament where the services of a revenue cutter were needed about as badly as ever happens.

In a stiff westerly gale, with both anchors down and dragging on a lee shore, rolling heavily in a cross sea, deck load shifted, and 5 feet of water in the hold, it seemed that this schooner's end was close at hand.

An attempt to shoot a line on board the distressed vessel proved futile, owing to the high wind.

The sea was too rough to lower the surfboat, but by a liberal use of oil the cutter was enabled to get a 4-inch line on board, by means of which a 10-inch hawser was secured to the schooner.