Members of the Weld family from Massachusetts were among North Haven Island’s early “rusticators.” Dr. Charles G. Weld, a Boston physician and philanthropist, purchased Iron Point, on the southeastern corner of the island, and in 1898 built a large summer home. His windmill pumped water from North Haven’s first artesian well. Dr. Webb took great interest in local affairs and the well being of year-round island residents. He kept his dock open during very cold winters when the town ferry dock was unusable because of ice. To facilitate more frequent mail delivery and communication with the mainland, Dr. Weld had the steamer Sylvia built.
Dr. Weld and his brother William were avid sailors. Charles attempted to sail around the world in his own yacht in 1886, but the boat was destroyed by fire in Yokohama harbor. That year William brought a new sailboat to the island aboard his schooner; it was the inspiration for the North Haven Dinghy, from which a whole racing class of gaff-rigged sailboats was born. North Haven boatbuilder James Osman Brown began building an improved version in 1888. Today North Haven Dinghies are the oldest continuously raced class of sailboats in the country, and J.O. Brown & Sons still builds boats on North Haven.