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Baldwin Road


Baldwin Road is a lane tucked behind Shelter Island High School, running perpendicular to Smith Street. Its namesakes were landowners and farmers, well-known on Shelter Island in the early 20th century.

According to the Shelter Island Historical Society, in 1900 members of the Baldwin family owned numerous properties across the Island, including Baldwin Farms, which consisted of 13.5 acres and a main house. Stephen C. Baldwin owned Hilo Farm in 1917, which is now a residential area.

He also owned 103 acres of Terry’s Neck, now Westmoreland Farm.

In a letter written in 1986, one friend of the Baldwin family, Dorothy Payne Fountain, recounted memories of Thanksgiving meals and traditions in the Baldwin home in the early 1900s. She described the “golden and quiet lanes of [her] beloved Shelter Island,” a place where she gathered with family and friends to celebrate the holiday.

At the time, the Baldwin main house belonged to “Uncle Ed Baldwin.” It boasted a “ballroom size front parlor” and was full of “curios and artifacts from all around the world.” Though the big Baldwin house burned down in 1927 — a “time of great sadness” according to Ms. Fountain — the memories of “every nook and cranny” remained with her.

Upon first glance at Baldwin Road’s street sign, it becomes clear that the thoroughfare also goes by another name: Admiral Harold E. Shear Memorial Drive. A local and national hero, Harold E. Shear was a highly decorated officer who graduated from Shelter Island High School in the class of 1937. Admiral Shear resided on Baldwin Road, hence the location of his memorial.

According to Reporter archives, the admiral was named vice chief of Naval Operations by President Gerald Ford in 1975, the second highest office in the U.S. Navy. Prior to that, he served as commander-in-chief of the U.S. Naval Forces in Europe, as well as commander of his own commercial fishing boat in his early teens.

The four-star admiral retired in 1980 at age 62, according to the Reporter, after 42 years of service.

He died in 1999 at age 80, and is buried at Arlington National Cemetery.

Although the street boasts the names of some of the Island’s most celebrated and beloved figures, who knows? Perhaps the next namesake is living on Baldwin Road right now.