High Street originally continued straight until the first bridge over the railroad tracks was constructed in 1906. From 1900 when the first trolleys came to town until the bridge was built, passengers had to unload here to switch from the trolley from Newburyport to continue through Ipswich.
Lathrop Brothers Coal and Ice Company harvested on the Ipswich River between Upper River Road and Haywood Street. Lines were drawn on the ice and horses dragged “groovers” along the line, cutting the ice about 6 to 8 inches deep. The ice was then floated to the ice house, where it was cut into blocks.
Eunice Caldwell attended Ipswich Female Seminary from 1828 to 1829, where she began a lasting friendship with Mary Lyon. She married the Reverend John Phelps Cowles in 1838, and returned to Ipswich in 1844 to reopen the Seminary, which they ran until it closed in 1876.