America’s first valentine in Oyster Bay?

Oyster Bay has been the home to much of America’s history, boasting celebrity residents like Theodore Roosevelt and buildings like the Octagon Hotel. But the story of America’s earliest documented valentine is little known, and it happened right on Main Street in what is now known as the Raynham Hall Museum.

Throughout the Revolutionary War, Redcoats quartered the homes of American families -- if they were loyalists families were spared; otherwise soldiers were authorized to shoot them on the spot. So, when British Colonel John Simcoe knocked on the Townsend family’s door in 1778, the patriot family took him in happily as a means of self-preservation. For the next year Simcoe and his men stayed in the Townsend home -- renamed The Homestead during British occupancy -- and it is believed Simcoe fell in love with the eldest Townsend daughter, Sally, according to museum educator Michael Goudket.

“We have documentation that the soldiers really did like Ms. Sally very much,” Goudket said. “There is a rumor that there was some love interest going on [between Townsend and Simcoe]; unfortunately we are unable to document it.”

On Feb. 14, 1779, Simcoe, who was in his 30s, gave a valentine to 19-year-old Sally.

“Fairest maid, where all is fair, beauty’s pride and nature’s care. To you my heart I must resign, oh choose me for your valentine,” Simcoe wrote. The poem goes on, but Goudket said the first few lines really sum it up.

The Redcoats’ endearment for the Townsends didn’t end with Ms. Sally either. Her brother, Robert, was a merchant in New York City. He returned one day to find the British soldiers occupying his family’s home. He befriended many of the soldiers, earned their trust, and then reported everything he heard from them to Gen. George Washington. The spy went undetected throughout the entire war, and historians didn’t figure out his identity until the 1930s.

History hasn’t revealed what happened immediately after Simcoe gave Sally her valentine, but in the end they didn’t live happily ever after. Goudket said Sally never married, and Simcoe, who was betrothed to another woman in England, married a teenage girl in Canada when Britain sent him there after the Revolutionary War. He founded Toronto while he was there. He died, possibly of an illness, shortly after the War of 1812 while traveling to India.