In the June 29, 1950 edition of the "Cumberland Evening Times" (of Cumberland, Maryland), Census District Supervisor Everard Briscoe mentioned that Highland Beach had 45 homes and five year-round residents, with all of the 45 homes being occupied during vacation season. In the September 18, 1968 edition of The Evening Sun (of Baltimore, Maryland), Highland Beach is described as a "44-acre retreat of 52 clapboard, shingle, and stucco cottages that date back to 1894 - plus 1,000 feet of waterfront where no pets or picnicking are allowed." A Dr. E. B. Henderson, 85 years old at that time, is named as the only surviving member of the 1922 incorporating committee. He is mentioned as the former head of Physical Education in DC Public Schools, with about 40 years of service there. According to Dr. Henderson, poet Paul Laurence Dunbar wrote "Ships that Pass in the Night," one of his most famous poems, while visiting Highland Beach. Mrs. Fannie Howard Douglass, widow of Joseph H. Douglass (grandson of Frederick Douglass), was in her 80s and living in the Twin Oaks home at the time of this article. Joseph and Fannie's son, Frederick Douglass, III, married Nettie Hancock Washington, the granddaughter of Booker T. Washington, joining two of the most esteemed Black families of the 19th and 20th centuries.