Obadiah Gildersleeve, Sr.

• Obadiah Gildersleeve, Sr Find A Grave Memorial# 70661884
• Portland Burying Ground, Portland, Middlesex County, Connecticut, USA
• Also Known as Center Cemetery

Christening was 28 May 1728 by The Reverend Ebenezer Prime of the Presbyterian Church at Huntington, Suffolk, New York.

Obadiah was the son of Mary Munn and Thomas Gildersleeve.

He married 14 February 1750 at Huntington, Suffolk, New York to Mary Dinge, first daughter of Esther Chichester and Richard Dinge.

He learned ship building at Sag Harbor, working for John Foster, one of the largest ship builders in Southhampton.

His wife and son, Richard, were buried in the old cemetery on the bank of the river opposite of Middleton. When excavations for brownstone in the nearby quarries encroached, they were removed to the "Eastern", or what is also known as the Center Cemetery, one mile east of Gildersleeve, Middlesex, Connecticut.

Obadiah had been buried at South Glastonbry, where he had spent the last of his life in the home of his oldest daughter, Esther. He, his wife and son are now together in the Gildersleeve plot at the Center Cemetery aka Portland Burying Ground.

DAR #A044561

Gildersleeve Pioneers, by Willard Harvey Gildersleeve, 1941.

Sylvester Gildersleeve's Descendants, by Willard Harvey Gildersleeve, 1952.

Moved from Long Island to Portland, Connecticut in 1776.

Obadiah and Mary were married by Ebenezer Prime. They removed to Sag Harbor, Long Island in 1762, and he was engaged in shipbuilding. He continued in this work after leaving Long Island in 1776. He made his home at Chatham, Connecticut. He then, with his daughter Esther, removed to South Glastonbury, Connecticut where he died January 5, 1816, aged 88. The births of the children of Obadiah are recorded in the Family Bible which was torn and worn so that some dates are missing.

First generation in Gildersleeve, Connecticut. Census of 1776, Southampton, East of Watermill, 5 M, 4 F. Baptised by Rev. Prime, Presbyterian Church. Married by Rev. Prime, Presbyterian Church.

The town seal of Portland, Conn., was created by a descendant of the Gildersleeve family of Crab Meadow, a family of shipbuilders displaced during the Revolutionary War who established a shipbuilding industry in that town that reigned for over 100 years. Photo Courtesy Town of Portland

Gildersleeve Steamships, The Crab Meadow Connection It is a well-known fact among those who study local history that the story of shipbuilding is deeply entwined in the history of Northport village. The single most important driving force for the local economy for the better part of the 19th century, the industry was led by a number of shipyard owners locally, fueled by the labor of full and part time workers, and resulted in ancillary businesses, from manufacturing to retail, which made Northport a fulcrum of economic well being on the North Shore of Long Island for many decades. Less well known, however, is the fact that a family of shipbuilders left the Northport area around the time of the Revolution, and established a shipbuilding enterprise on the Connecticut River that fueled a village of its own. That family was the Gildersleeves – descended from the original Richard Gildersleeve who moved with the Puritan diaspora from Wethersfield to Stamford and Hempstead to Newtown – and firmly established prior to the Revolution on land in Crab Meadow. The Gildersleeve built wooden steamships for decades in the town of Portland, Conn., just south of Hartford along the Connecticut River, and in fact a section of the town became known by the name Gildersleeve in honor of their influence. And while the business went into decline and closed in the early 20th century, the Gildersleeve family's name continues to be a significant one in the local history of that region. It all started with Richard, however, who was an original proprietor of Wethersfield before procuring with others a patent from the Dutch for Hempstead. Along the way he was a magistrate, and a representative to local governments. It was his grandson, also named Richard, who settled in Huntington and established a family farm in 1683 on 22 acres in Crab Meadow, "5 or 8 acres at ye hed of claboard hollow and the remainder of it betwisxt William Brodeton and his owne land facen against Crabmedewe," according to the Huntington Town Records. For half a century, the family prospered in Crab Meadow it would seem – in 1740 we find Thomas Gildersleeve, Richard's son, is a Trustee for the Town of Huntington. The Revolution disrupted that prosperity however. In The Refugees of 1776 records, we find several members of the Gildersleeve family having become displaced to Connecticut, including brothers Benjamin and Obadiah. Benjamin's descendants went on to become prominent in varied locations around the country – from Virginia to Colorado – with evangelists, philologists, architects and engineers named in cities like Denver, Baltimore, Detroit and Chicago. As for Obadiah, it was he and his children who moved to Connecticut and established the Gildersleeve shipyards in Portland. Obadiah's route took him through Sag Harbor, in fact, with his 'effects' being shipped from that town to Saybrook on September 2, 1776. We learn from the Refugees volume that Obadiah had already gotten involved in shipbuilding while in Sag Harbor, in fact – and after the Revolution, remained in Connecticut, and "continued in his work after leaving Long Island... at Chatham, Conn." Obadiah's sons Henry, Philip and Richard, went with him. Henry had served in Colonel Smith's Regiment, as had Philip. Philip, it seems, was a master carpenter, and had been working with his father in shipbuilding in Sag Harbor. After the war, he was master carpenter of the ship of war Connecticut, built in 1799 at 513 tons and 20 guns, which General Seth Overton contracted to build for the government. The former Crab Meadow residents found opportunity and fortune on the Connecticut River, but not before the family's story was nearly marred by tragedy. It seems that Philip was nearly drowned on the river in 1801, according to Portland historical accounts when on a particularly cold winter evening he and friends, "in attempting to return in the evening in their small rowboat ... were surrounded by floating masses of ice, which soon crushed through their said boat and left them in the water among the broken ice. They then by a great effort turned over their broken boat and all of them got upon the bottom of it where they remained for a long time before they were rescued." Among the rescuers was Henry Gildersleeve, only 16 years old at the time. This near tragedy put behind them, the Gildersleeves went into business with a vengeance in their adopted community. Philip's youngest son Sylvester Gildersleeve (1795-1886), is considered the one who made the area famous for its shipbuilding. Trained in Philip's yards, during the War of 1812 he established his reputation at the age of 20 by taking 500 men to Sacketts Harbor NY to build what was to that point in time the largest fighting ship ever to sail for the US – a 100 gun vessel. Two of them, in fact, built side by side during the winter of 1815 as the war dragged on. As it turned out, a declaration of peace was declared before Sylvester and his crew could finish the job, but his name was now known as a shipbuilder to watch. On his return to the family business, Sylvester expanded his father's yards by purchasing shipyards from the Churchills (1828) and the Lewis yards (1838). The first vessel he built was a sloop, which became known as "The Boston Packet," at 70 tons, captained by Seth Overton. He built the William Bryan in 1836, said to be the first packet, which sailed from New York to Texas. Five more ships soon followed for this same route. Among other initiatives, he contracted to build the ships to send brownstone building blocks to places as far away as New York and San Francisco. Sylvester Gildersleeve also set up several other businesses on the street, including a carriage factory, a mattress shop, a sawmill, and an icehouse. He built tenements for the Swedish immigrants he employed in his shipyards and factories. There was a Gildersleeve General Store built in the 1850s. From 1872 to 1952 the Gildersleeve Post Office occupied part of the Gildersleeve Store. Sylvester also built the Cayuga, a gunboat, for the Civil War. Sylvester's son Henry continued the family tradition, going into partnership with his father at the age of 25 and extending the family's reach into New York City, where he associated with the shipping and commission firm of Bentley, Gildersleeve & Co, on South Street. Meanwhile back at the shipyards, business continued to expand. In WWI, the firm built a number of submarine chasers. They expanded into marine transportation along the New England coast, tobacco growing, coat manufacturing and more. Henry's sons Sylvester and Oliver continued in the trade. Well into the mid-1900s, their daughters married well – Jane Gildersleeve to the heir of the EE Dickinson Witch Hazel manufacturing company, Ann to a theologian. But in time, the shipbuilding industry declined, and the Gildersleeve shipyards closed their doors in 1932. In 1939 the family's estate, including the 1815 house with its four massive white columns and acres of lawns and gardens, was sold to a doctor from Hartford. The town known as Gildersleeve ceased to exist, subsumed in present day Portland. But fittingly, and in memory of the importance and influence of the transplanted Crab Meadow Gildersleeves, when it came time in 1966 to create a town seal for Portland, that town turned to the great grandson of Sylvester – artist Philip Gildersleeve – to do the job. back to top

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