William J. Barton wrote about this photo in 1963: “Upper High Street before the bridge was built over the Boston and Maine RR. The house on the left was the George Harris house, now owned by Lydia Harris. The barn, and then the old house; part belonged to Jennie Butler. The house across the track was Nat Burnham’s house, moved to Locust St. The house facing was on the corner of High and Town Farm Road, now on Locust St., and the front faces High under the bank of the road over the RR bridge
High Street originally continued straight at 110 High St. (the John Kimball Jr. house with the blue tree house) until the first bridge over the railroad tracks was constructed in 1906. From 1896 when the first trolleys came to town until the bridge was built ten years later, passengers had to unload here to switch from the trolley from the Georgetown trolley to continue through Ipswich.
When the first bridge was built the roadway was moved a bit to the east. The recently rebuilt bridge is in that same location.
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.
Historic Ipswich 