High Street originally continued straight at the John Kimball Jr. house (the one with the blue tree house) 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.
Shown below is an old photo of High Street before the first bridge was built across the tracks. High Street crossed the tracks at grade and continued straight on what is now a dead end section of old High Street ending at Kimball Avenue.
When the first bridge was built crossing the tracks on High Street in 1906 the roadway was moved a bit to the east. The newly rebuilt bridge is in that same location.