In 1896, the first trolley from Beverly arrived in Ipswich, and a year later, the Georgetown, Rowley and Ipswich Street Railway opened. By 1919, Mr. Ford's Model T ended the brief era of the street railway.
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.