The hurricane of 1938, also known as the Long Island Express, hit Long Island on a Wednesday on September 21, 1938. Though eastern Long Island received the brunt of the storm, Freeport was not left unscathed. Power was lost throughout the village, leaving traffic lights inoperable. Freeport Hospital used candles in all rooms and had an automatic lamp ready for use in an operating room.
A shed on a dock in Freeport Point was blown into Randall’s Bay, and was last spotted floating towards Jones Inlet. South Long Beach Avenue was underwater as far north as Ray Street. Many residents of south Freeport were marooned in their homes after the storm. An hour before high tide, Freeport Point was three feet underwater.
Newspaper articles concerning post hurricane boat damage in Freeport are contradictory. The New York Times reported that there were “heavy losses to owners of boats” in Freeport. Whereas, a headline in The Brooklyn Daily Eagle claimed that “all Freeport craft escape storm damage.”
One boat, owned by Frank Fraser, lost its moorings and drifted to the opposite side of the canal where it was recovered a few days later. A waterspout was reported after a water main broke at Ray Street and Gordon Place. Trees throughout Freeport fell, including several trees near Our Holy Redeemer Church that blocked South Ocean Avenue when they hit the ground. A telephone pole snapped at Claurome Street and North Main Street. Mayor Robert E. Patterson estimated the Village sustained $200,000 worth of damage due to the hurricane. Miraculously, no deaths or serious injuries were reported in Freeport. On September 28, 1938, 500 WPA (Works Progress Administration) workers gathered in Freeport to catch a special train to the Hamptons to help remove debris, repair roads, and restore drainage ditches.