The Bayside Yacht Club was founded on July 9, 1902 with the intent to promote sailing and socializing among its members. The following year the club incorporated complete with elected officers, a set of by-laws, and a roster of 70 members.

The original clubhouse for the Bayside Yacht Club was a barn taken in 1904 from the adjoining property owned by George Bradish, Jr. The barn was expanded and the remodeled clubhouse included a large dining area, kitchen and forty "bath houses" complete with lockers and showers.

Throughout the years the club had encountered several setbacks including two devastatingly destructive hurricanes, one murder, and two fires. The first fire was set by an arsonist in 1908. It was after the 1908 fire that the clubhouse expanded from the original barn and an addition of a billiards room and eight guest rooms to accommodate overnight visitors. It was also in 1908 that the murder of William Annis occurred at the Club. Annis was a participant in an afternoon race and was shot by Peter C. Hains in what appears to have been a jealous rage. The second fire began in the club's kitchen in 1968. After that fire, a larger, Olympic-sized swimming pool was built to replace the original 1958 pool which was used exclusively for the Club's members and guests.

This postcard of the Bayside Yacht Club dates from 1917.