America’s First Valentine – A Visit to Raynham Hall Museum

It’s that time of year again when class lists are sent home and children address Valentine’s Day cards to their classmates in anticipation of a celebration filled with hearts, flowers, red and pink. The time-honored tradition of sending Valentine’s Day cards with notes of love and appreciation has been practiced in the United States for many years – but have you ever wondered exactly how many?


The first documented Valentine ever sent in America was penned in 1779 during the Revolutionary War in Oyster Bay, Long Island at the former home of the Townsend family. This former residence is rich in history and has since been turned into a beautiful museum: Raynham Hall, located at 30 West Main Street in downtown Oyster Bay – approximately 25 miles northeast of New York City. I was lucky enough to tour this unique museum and hold a special Elephant Organics photoshoot there in celebration of Valentine’s Day, and our brand-new Love Notes print pajamas (available for a limited time in sizes NB – Women’s XXL). I was enchanted by the beautiful building, captivated by the story of America’s First Documented Valentine, and surprised to learn that this very building was also home to a prominent member of a Patriot Spy ring.



In order to understand the background and ill-fated romance surrounding America’s First Valentine, it is necessary to delve into the history books. In 1776, the Declaration of Independence had been freshly penned, and the British King George III, was none too pleased. Subsequently, The Battle of Long Island (or The Battle of Brooklyn as it is also known) marked the first major battle of the Revolutionary War after the Declaration of Independence was signed. This proved to be a disastrous defeat of the American Continental Army and George Washington by the British. After the battle, British forces occupied New York City and Long Island.

The British occupation on Long Island included the house that is now the Raynham Hall Museum. At the time, it was home to Samuel Townsend, the owner of a prominent shipping fleet, his wife Sarah Stoddard Townsend, 8 children, and 20 enslaved people. Importantly, the Townsend family were Patriots. In fact, Samuel narrowly avoided capture and imprisonment by British troops early in the occupation. He was forced to sign an oath of allegiance to Britain and the King. For a period of six months during 1778-1779, the Townsend home served as headquarters to the Queen’s Rangers, a British regiment of over 300 troops, and their commander, Lt. Col. John Graves Simcoe. Simcoe moved into the Townsend home and lived alongside the family. Daily officers’ meetings were held in the front parlor – which in the present-day Raynham Hall Museum is set with furnishings to resemble what it may have looked like during that time.


It was Lt. Col. John Graves Simcoe who penned the United States’ first Valentine. The Valentine was written as a poem, and was addressed to the Townsend’s daughter, Sarah. It was presented to her on February 14th, 1779. The poem, which can be read in its entirety in the picture below, or on the Raynham Hall website here, describes Simcoe’s infatuation with Sarah, and the difficulty of loving an enemy. Ultimately, it appears as though Sarah did not choose Lt. Col. Simcoe for her Valentine, perhaps due to their vast political differences. Following the war, Simcoe went on to found the city of Toronto, where he served as Governor of Upper Canada. Sarah remained in Oyster Bay until her death in 1842.


Besides the notable delivery of America’s First Valentine, Raynham Hall and the Townsend family are also famous for their involvement in the Culper Spy Ring. This intelligence network provided George Washington with information that was invaluable to the Patriots’ cause. The Townsends’ son (Sarah’s brother) Robert, operated under the code name Culper Junior and served as an important link in a chain of agents. In what reads like the stuff of spy novels, the agents formed an intricate spy network with notes penned in invisible ink and carried via whaleboat to wherever Washington was headquartered.

First Valentine - Raynham Hall

The exhibits at Raynham Hall Museum include a replica of America’s First Valentine (the original copy went missing sometime in the 1920’s), Sarah’s bedroom, the family dining room set up with some of Robert’s merchant wears, and many more rooms adorned with beautiful historical furnishings. Much to the Elephant Organics models’ delight, one of the current exhibits includes beautiful antique toys and even a dollhouse. The models enjoyed observing the toys during their shoot and comparing them to their own modern-day toys. If you would like more information about Raynham Hall, America’s First Valentine, or the Culper Spy Ring, visit their website here. You can even take a virtual tour of the museum here.

Special Thanks To:

Raynham Hall and their Board of Trustees

Harriet Gerard Clark, Executive Director

Theresa Skvarla, Assistant Director

Jessica Pearl, Collections Manager

Joanna Badami, who loaned many of the toys shown in our photoshoot pictures from her collection

Shop our Love Notes Print Collection!