In the early 19th century before the railroads came in, there were dozens of ship captains around Westport. The most notable were the Sherwood triplets. Frederick, Franklin, and Francis were born in 1810, the youngest of 10 children, who all left their Sherwood Island home at age 16 for the adventure of the high seas.

Their father, Daniel

Sherwood, had built a house on Sherwood Island. The first Sherwood came to Connecticut from England in the late 1600s. By Daniel’s generation, there were many branches of the Sherwood family. The Sherwood triplets, even as grown men, were known to enjoy the confusion caused by the fact they looked very similar. They all lived in Westport for their entire lives when they were not exploring the globe.

Capt. Frederick Sherwood sailed to China and Japan shortly after Commodore Perry opened American trade to the East in 1854. Frederick sailed to Brazil for coffee and made six trips around Cape Horn to California during the gold rush.

During the Mexican-American War from 1846 to 1848, Capt. Francis Sherwood and the ship Carolina bore Gen. Scott’s dispatches to New Orleans announcing the capture of Mexico City, and the surrender of forces.

Capt. Franklin Sherwood engaged in trading with Havana, New Orleans and Texas ports, as well as travelled to Chinese and European seaports.

Westport continues to attract today’s captains of industry, as many of the leaders in the business community make Westport their home.

Margaret Mazer for the Westport Historical Society. For information on Tours, Programs, and Membership, Please contact