Captain Joshua Watts took out a display ad (one of the few for any of the Maryland Green Book listings) in the 1939 Vacation Section to advertise his availability to take tourists fishing either in the bay or on Kent Island, which is a large island on the east side of the Chesapeake Bay. Love Point is at the north end of the island where the Chester River enters the Bay. The river and bay around Love Point support rock fish, trout and catfish which all provide good sport fishing. 

 

In the late nineteenth and early twentieth centuries, Captain Jacob Fillmore “J. Fill” Legg managed the Love Point Hotel for the Love Point Beach and Park Company as a resort hotel on the northeast side of the island. Legg’s entries in the US Censuses for 1880 and 1900 show that he worked as a mailman and was also a waterman. A waterman’s life is seasonal and it appears that by the time Legg was in his late forties, he had stopped working the water and took up management of the hotel, which provided boats to guests for fishing in the bay or the river. 

 

The 1920 U.S. Census, notes Watts as a watchman for a hotel and the proprietor is noted as J. Fillmore Legg. Although not specified, it appears that Watts had access to the hotels boats and likely served as the crew when taking out fishing parties. Legg died in 1924, but the hotel continued in operation, advertising itself in the 1930s as a “family hotel on the Chesapeake.” Watts used the opportunity to advertise his availability at an uncertain time for the hotel which depended on receiving customers who came by train or ferry. The start of World War II ended tourism on Kent Island. The 1950 Census is the last one that Watts appears in, and at 68 he had stopped working and was living in a cottage that likely belonged to the local canning factory.