The Highlands

The two hills of the Highlands section of Winthrop were originally part of the 1636/7 allotments by Boston to William Pierce, Thomas Buttalph, John Sanford and William Aspinwall. On October 26, 1649, the farm was conveyed to Deane Winthrop. By the mid to late 1600’s, Deane became the owner of the entire Highlands as well as the Beach and Point Shirley areas. This was then known as the Winthrop Farm where Deane lived until his death in 1703/4. His family continued ownership of the Deane Winthrop house through about 1750.

The Highlands, from Summit Avenue on Floyd’s Hill to Grover’s Cliff just beyond Prospect Hill, was purchased by the City of Boston in 1866 for the purpose of building an Insane Hospital. It was called the “City Farm” and subsequently deemed a poor location for such a facility being so far from the city and so close to the ocean. Instead the Hospital was built in Danvers and the Winthrop area lay dormant. As was the existing custom, this land continued to be used by the public for bird hunting. There used to be a fresh water marsh called Coomeys Pond near the corner of what is now the junction of Grover’s Ave and Nahant Ave. A small cabin called Gove’s Shanty was nearby where the men of the town often gathered in the evening to fish, tell stories and have a nip or two. In 1883 the entire City Farm was purchased by William Rice who had it surveyed for building lots and started developing the area.

In 1875 the southern side of Floyd Hill, was surveyed for building lots and Almont, Locust and Shirley Streets began to be developed. The area was called Floydonia since a number of Floyd families lived along Revere Street and on the hill crested by Summit Avenue.

Then in 1890/1 the Fort Banks Area and Grover’s Cliff (later called Fort Heath) were acquired by the U.S. Government and the two forts were constructed.

In 1914, the Highland Yacht Club was formed and a clubhouse built on Nahant Avenue by the water. The club remained active until World War II at which time the building was used for a U.S.O. entertainment center. The clubhouse later became and still is a private residence. A picture of this building when used as the U.S.O. Club is shown below.