The first settlers of Ipswich forded the river near the Ipswich Mills dam, just as native Americans had done. Tide flows up the River to that location twice a day. In 1639 the General Court ordered that each town begin construction of America’s first highway, the Bay Road, from Boston to Portsmouth, and five years later a wooden cart bridge was built over the river. The bridge frequently fell victim to age and weather, and was rebuilt several times. In 1764 the stone arch Choate Bridge was constructed, and was doubled in width seventy years later to carry the increased traffic of stagecoaches arriving in town.
The American Society of Civil Engineers cites the Choate Bridge as the oldest two-span masonry arch bridge in America, and the oldest extant bridge in Massachusetts. It was added to the National Register of Historic Places in 1972. The designer and supervisor of construction was Col. John Choate, who encountered opposition from some townspeople who doubted a bridge built from stone would stand. There is an old legend that on the day that the wooden forms were removed, his horse was tethered nearby so that he might mount and escape should the bridge collapse. Today the Choate Bridge carries thousands of cars daily through downtown Ipswich Rts 1A and 133. Two other stone arch bridges stand nearby on County Street and Green Street, in addition to the triple-arch Warner Bridge on Mill Road.