Sylvester Gildersleeve

Sylvester, the subject of this sketch, was born February 25th 1795, in the little old two story red frame house situated on Indian Hill, at the northerly end of Chatham (now the portion of Portland called Gildersleeve). He attended the district school until he was eighteen years of age. he then commenced work in his father's shipyard. This was during the war of 1812, at which time, owing to the operations of the British army in Canada, our government was engaged in constructing war vessels on the western lakes. In 1815, when young Gildersleeve was but 20 years of age, he went, in company with some 500 workmen, to Sackett's Harbor, N.Y., to build for the government a one hundred gun ship, which was then one of the largest ever built in this country - the combined fleet of Commodore Macdonough at the battle of Lake Champlain mounting but 86 guns. Two of these monster ships were being constructed at the same time. The weather was cold and the men were provided with a liberal supply of 'grog,' then considered an indispensable part of the rations. The ships were never completed, as the declaration of peace soon after rendered them useless, and the men returned home, some of them making nearly the whole journey on foot.

Soon after his return to Chatham young Gildersleeve started in business for himself. His first vessel, built in 1821, was a one hundred ton vessel, called the BOSTON PACKET. Since that he has constructed upwards of one hundred vessels of from one hundred up to fourteen hundred tons each, one of which, the ship S. GILDERSLEEVE, was burned by the privateer ALABAMA, and paid for by the government, out of the Geneva award. He continued in active business up to within seventeen years past, and has lived to see his sons and his grandson succeed him in the same business, his grandson, Oliver Gildersleeve, now engaged in shipbuilding, being the fifth generation in that business at the same place...

In connection with William and Joseph J. Hendley, and Alexander Keith, of Middletown, he built, in 1836, the schooner WILLIAM BRYAN, the first vessel that ever sailed from New York to Texas as a regular packet. From that vessel the New York and Galveston line of packets was formed, consisting at first of five ships and two barques, all but one built by him. Messrs. John H. Brower & Co. were the New York, and William Hendley & Co. the Galveston agents of the line, which continued up to the breaking out of the Rebellion in 1861."