Wonderful to see the Douglass Family celebrating ancestor Captain Fred Douglass with a Rocky Neck Plunge of their own! And I was glad to learn the name of the beach is Flynn’s Beach, not Oak Cove Beach. The Community Heritage Map of Cape Ann, 1889, does not give a name to the beach on Oakes (note spelling of Oakes) Cove, however, many long-time residents refer to it as Flynn’s Beach. Upon close inspection of the map of 1889, several of the properties abutting Oakes Cove belong to S.W. Oakes. In the Douglass’ post of yesterday, Oakes Cove was referred to as Wonsons Cove. Wonsons Cove is the cove just south of Oakes Cove, which you see to your immediate left when crossing the Rocky Neck Avenue causeway on your way into Rocky Neck.
On the old map, we can see our home on Plum Street, which was built in 1851, and can barely make out the name of the owner of 1889–it appears as though the last name is Douglass–perhaps relatives of Captain Fred Douglass and the Douglass family? Our home is on the eastern side of the former Point Grammar School. The house on the map on the western side of the school is more clearly labeled and that too is owned by a Douglass, either S.G. or S.C. Douglass.