The town of Portland has a rich history of shipbuilding. Launching its first vessel in 1741, Portland, like many river towns in Connecticut, built numerous ships for local industries, as well as for military protection during the American Revolution and the War of 1812. Perhaps the most recognizable name in the history of Portland shipbuilding is Sylvester Gildersleeve, the man for which a large section of Portland is still named today.

Sylvester Gildersleeve from History of Middlesex County, Connecticut, with Biographical Sketches of Its Prominent Men by Henry Whittemore

Born on February 25, 1795, Sylvester Gildersleeve was the fifth of six children born to second-generation shipbuilder Philip Gildersleeve. Sylvester’s grandfather started the family business in 1776. When Sylvester turned 18 he entered his father’s business, then quickly relocated to the lakes region of western New York to build ships to bolster area defenses during the War of 1812.

Gildersleeve Builds Ships in Portland

Sylvester returned to Portland after the war and in 1821 began building ships under the name S. Gildersleeve & Sons. Between 1821 and 1844, the firm produced 135 vessels worth approximately $2.5 million. After purchasing a shipyard from builders Charles and David Churchill in 1828, S. Gildersleeve & Sons went on to produce some of the most famous ships in US history.

In 1836, Gildersleeve launched the schooner William Bryan, the first vessel to make regular voyages between New York and Texas. The journey proved so successful that investors established a regular New York and Galveston Line. Between 1847 and 1850, S. Gildersleeve & Sons built five ships for this line, naming them all after Texas patriots. The line continued operation right up until hostilities broke out between the North and the South in 1861.

An Early War Casualty and a Continued Legacy

One of the early victims of Civil War hostilities was the 1,400-ton S. Gildersleeve. Built in 1854, the ship, while carrying coal on a voyage to China, fell prey to an attack by the Confederate cruiser Alabama. The Gildersleeves did more than produce commercial vessels during this era, however. One of the company’s most important and substantial builds was the steam-powered gunboat Cayuga built for the US government in 1861. Three years later, the family completed work on the United States, the largest steamship in the country, weighing in at 1,600 tons.

Despite Sylvester’s death in 1886, the Gildersleeve legacy in Portland lived on. During the height of his shipbuilding operation, Sylvester opened a mattress factory, wagon shop, and general store in town. His son and grandson ensured the shipbuilding company operated well into the 20th century. Other members of his family served the town as teachers, its first postmaster, and in a variety of other occupations ensuring that when the Connecticut River flood of 1936 brought devastation to local industries—and thus an end to the Golden Age of shipbuilding in Portland—the Gildersleeve name continued to play an important role in shaping the town’s identity.

USS Gildersleeve on the launching ways, Portland, 1917. The vessel was listed as a United States Shipping Board Emergency Fleet Corporation vessel in 1919 – Gildersleeve Ship Construction Company – Mystic Seaport and Connecticut History Illustrated