It was the summer of 1892, and Maj. Charles R. Douglass, a Civil War veteran, was getting hungry. He and his wife, Laura, headed to the grand Bay Ridge Hotel, then referred to as “the queen resort of the Chesapeake,” hoping to have a meal.
They were turned away because they were black.
So Douglass decided to start a resort where African-Americans of means could spend their summers. He purchased a plot of land just south of Annapolis along the Chesapeake Bay, naming it Highland Beach, and selling parcels to family and friends.
His own father, famed abolitionist Frederick Douglass, bought a tract of land there in 1893, where he planned to build Twin Oaks, his summer cottage. From there, he would be able to look across the bay to the Eastern Shore, where he had once been enslaved.
Over the years, the likes of Booker T. Washington and W.E.B. Du Bois owned homes or paid visits to Highland Beach, according to an article in The Baltimore Sun archives. By the 1920s, The Afro reported, the town had become as swanky and exclusive as Monte Carlo or a beach in Southampton, allowing in only the wealthy elites of Baltimore and Washington’s black society, and barring uninvited guests.
Frederick Douglass died before he could see his summer home completed. One hundred years after his death, the state of Maryland and Anne Arundel County acquired the house for $500,000 and deeded it to the Highland Beach community, according to The Sun archives. Today, the Frederick Douglass Museum and Cultural Center, once known as Twin Oaks, still stands in Highland Beach. It’s open by appointment.