Gilpin Point is located on the Choptank River opposite the mouth of Tuckahoe River at the end of Gilpin Point Road. A ferry ran across the river to Price's Landing on Tuckahoe Neck. Vincent Price was paid 500 pounds of tobacco to serve as the ferryman in 1776 until the "end of November Court." Colonel William Richardson, a Revolutionary hero, lived here. He became the Colonel of the Eastern Shore Battalion of the Maryland Flying Camp and then commander of the Fifth Regiment of the Maryland Line. Supplies for the Colonel's regiment were received at his landing at Gilpin Point. Richardson was part owner of the sloop Omega, which is reputed to have carried "parched corn" to the West Indies and returned with coral stone as ballast. Richardson's tobacco warehouse was also located at the site. All that remains of his home is part of a wall partially built of the coral brought from the West Indies, a possible brick dairy structure and crumbling tomb of Richardson.
Caleb Clark Wheeler, founder of the Wheeler Transportation Line, was born at Gilpin Point in 1839, worked as a cook on a schooner between Gilpin Point and Baltimore in the early 1840s and operated a general store at the wharf at Gilpin Point from 1862 to about 1870. Local farmers, towns' people and sailing vessels bought and traded at the store. 70 The landing is identified as "Gilpin's Point P.O." in the 1875 Caroline County map found in The 1877 Atlases and Other Early Maps of the Eastern Shore, Maryland.