Program

Legends & Lore®

Subject

Legend, People, Site

Location

93 Jermain Ave, Sag Harbor, NY 11963, USA

Lat/Long

40.994163, -72.294103

Grant Recipient

Sag Harbor Historical Museum

Erected in 1820 for Revolutionary War patriot Captain Lester Beebee (alternatively spelled Beebe), the Beebee Windmill was built by Amagansett millwright Samuel Schellinger and stood prominently on Sherry’s Hill along Suffolk Street. Its location overlooked Sag Harbor at the height of the whaling industry, when long‑distance voyages brought fleets of ships back to port. According to local legend, a flag was raised atop the windmill whenever a vessel was sighted in the bay, signaling the community below — a practice that gave rise to its enduring nickname, “Flag on the Mill, Ship in the Bay.”

The story entered popular lore through Victorian‑era writer and Sag Harbor resident Mary B. Sleight, who featured the windmill in her 1887 fictional novel The Flag on the Mill. The tale was later echoed by historian Harry Sleight in Earlier Days in Sag Harbor (1930) and cemented in local history through Dorothy Ingersoll Zaykowski’s authoritative 1991 volume, Sag Harbor: The Story of an American Beauty. Following Captain Beebee’s death in 1832, the windmill was put up for sale and was purchased in 1835 and relocated to Bridgehampton, where its legacy as a landmark of maritime observation and community memory continued.