The early 1700's saw the sparks of a new town in Southern Maryland named Leonardtown.   With it, William Maria Farthing purchased some 1,891 acres of land, lining Breton Bay's waters edge.  He titled it Hanover Farm.

In 1850, as the country was being tormented over the effects of slavery, Hanover Farm was purchased by Aloysius Fenwick, who later sold a portion of the land to John Wilkinson.  The two properties were divided by a stream, dubbed Hanover Run.

John Wilkinson found himself amidst a prospering town and country in the 1920's.  He constructed a store and home on his newly purchased land, and subsequently, leased the store and home to Tub Hall for use as a tavern.  He named it "The Willows" in honor of the graceful willow trees surrounding the property.   The original house, known as Willows Cottage, remains behind this present day restaurant.

It is rumored that during the thirteen years of Prohibition, the bar was closed but bootleg whiskey and homebrew could be bought at Willows Cottage.   After over half a century as a St. Mary's County landmark, the Willows has enjoyed an ongoing legend as one of the most respected and longest existing restaurants in the County.