Milton Road began as a Native American footpath and one of Rye's first roads. In the 17th century, gristmill roads developed along the Blind Brook, where local farmers brought grain to be processed into flour. Farmers soon shipped produce by market boat to New York, and Milton Road filled with wagons waiting to unload farm products at the boat landing and buy supplies from Gedney's store. The area also became a boot-making center, with boots made entirely by hand and local residents specializing in different parts of the boot. Many ship captains lived in houses along Milton Road, and boat building became an important part of the local economy. David Kirby, Jr. established his famous boatyard in the 1850's where Milton Harbor House is now located, and the Kirby boatyard built successful racing yachts, including an America's Cup winner and two contenders. Later owned by William Edgar John, the boatyard also built PT boats for the Navy during World War II. The Little Yellow Schoolhouse at #630 Milton Road, now a private home, was built in the 1830s on land given by the Halsted family, and by 1898 its enrollment had doubled from 30 to 60 students, leading to the opening of a new brick school building on Hewlett Avenue that still operates today as Milton School.