Hometown History: Lady Strong and the Oakwood Estate

Hometown History: Lady Strong and the Oakwood Estate

The Old Homestead stood near the corner of what is now Port Jefferson’s Winston Drive and Crystal Brook Hollow Road. Photo by Arthur S. Greene; Photo from Kenneth C. Brady Digital Archive

What is now Belle Terre, coupled with an area in today’s Port Jefferson, once comprised the 1200-acre Oakwood estate.

Surrounded on three sides by water, the property featured a country house, tilled land, woodlots, a hothouse, fruit and nut trees, sheepfolds, springs, an icehouse, a dairy, pigpens, barns and outbuildings.

The estate even included a private cemetery, the Sugar Loaf Burying Grounds, where some of Oakwood’s workers and their family members had been interred.

Mary B. Strong, known as “Lady Strong,” presided over the estate. In 1880, she was considered the wealthiest woman in Brookhaven Town, where she numbered among its largest taxpayers.

Oakwood is depicted on this portion of J. Chace’s 1858 Map of Suffolk County, L.I., New York. Photo from Kenneth C. Brady Digital Archive

William A. Hopkins and Charles A. Davis, Miss Strong’s trusted overseers, supervised day-to-day operations at Oakwood, everything from milking cows to cutting cordwood.

Lady Strong and her servants lived at the estate’s Old Homestead which stood near the corner of what is now Port Jefferson’s Winston Drive and Crystal Brook Hollow Road.

A short walk from tranquil Mount Sinai Harbor, the country house was the scene of elegant parties hosted by Miss Strong and surrounded by grounds lovingly tended by a gardener.

Responsible outdoorsmen were welcomed at Oakwood, where they hiked its shaded paths, hunted, trapped and gathered berries. Vacationers from Bridgeport, Connecticut sailed across Long Island Sound and pitched tents on the property at Camp Woodbine, while day-trippers picnicked on the estate at Saints Orchard.

After Lady Strong’s death on April 9, 1885, Oakwood reverted to her nephews, but through neglect, the once well-maintained estate went to ruin.

In spring 1901, surveyors were seen marking Oakwood’s boundaries and that winter advertisements had appeared in the New York Times announcing the property’s sale.

The Old Homestead stood near the corner of what is now Port Jefferson’s Winston Drive and Crystal Brook Hollow Road. 
Photo by Arthur S. Greene; Photo from Kenneth C. Brady Digital Archive

Clinton L. Rossiter, vice president of the Long Island Loan and Trust Company, purchased Oakwood from Mary B. Strong’s heirs in 1902. Rossiter represented a group of investors who planned to build a “private residence park,” known today as Belle Terre, on the land.

Over the ensuing years, the site was developed, and the Old Homestead was destroyed in a suspicious fire, leaving only street names such as Oakwood Road as reminders of Lady Strong and her vast estate.

Kenneth Brady has served as the Port Jefferson Village Historian and president of the Port Jefferson Conservancy, as well as on the boards of the Suffolk County Historical Society, Greater Port Jefferson Arts Council and Port Jefferson Historical Society. He is a longtime resident of Port Jefferson.

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