Michael McDeavitt became the proprietor of the 1870 Ocean House, renamed the Shippan House, and by 1890 he also had a pavilion and bathing houses, plus a casino 2 stories high on the property. In May of 1890, John Muzzio bought a merry-go-round from Asbury Park, New Jersey, and operated it on McDeavitt's grounds.

(In 1905, Muzzio purchased the grounds of the East Side Rod & Gun Club, near the horse race track, the site of Marina Bay condominiums today, and moved the carousel there. The carousel building remained on the grounds until the late 1970's).

Another commercial enterprise opened in Shippan in 1887, when John Ennis purchased acreage at the southwest end of the Point and erected a unique bathing pavilion in the waters, where patrons could enjoy the saltwater beneath a roof. Ennis cleared the area for ball fields, and his shed for 150 horses proved far too small for the many patrons using the facilities.

The pleasures of Shippan intrigued many, especially the increasing numbers of yachtsmen, and in September 1890, The Stamford Yacht Club was formed. Early in the spring of 1891, William A. Lottimer was elected its first Commodore, and four acres of land were purchased on the western shore at the curve of the bay. Within three months the new building was completed by N.W. Barrett of Bridgeport, and the next year adjacent land and buildings were purchased. The club advertised equal facilities to the families of members in all sports and pleasures yachting, bathing, tennis courts, croquet grounds, concerts, receptions, etc. In the years that followed, a fleet of Stamford Schooners raced the Sound waters, while youngsters of the club enjoyed the Red Wing class, built locally at the Luders boatyard, located west across the harbor from the yacht club. In 1913, a tragic fire swept through the clubhouse buildings, but within a year a beautiful new structure took its place. Another boating group, the Halloween Yacht Club, was organized in 1926 and flourishes today on the west edge of Cummings Park.