The brief era of horse-drawn trolleys apparently never materialized in Ipswich. Electric trolleys occupied the streets of Ipswich in the early 20th Century. A trolley line from Beverly through Hamilton to Essex and Gloucester opened in 1895, and on June 26, 1896, the first car on the branch that followed Candlewood Road to Ipswich arrived in town, greeted by a large crowd at Market Square. On that day, hundreds of people took advantage of the free ride to Essex Junction, some enjoying it as many as three times!

early trolley on South Main Street
Early four-wheel trolley on South Main Street arriving on the line from Beverly and Essex

The following year, the Georgetown, Rowley and Ipswich Street Railway opened, but its tracks ended at the High Street crossing of the B&M railroad, Passengers wishing to continue through Ipswich had to walk the distance from High Street to Market Square to change lines. In 1906 the town and B&M railway gained permission from the Massachusetts Grade Crossing Commission to construct the High Street Bridge. and on July 1907, the first set of improved eight-wheel trolleys crossed the bridge, making it possible to go from one end of Essex County to the other for 15 cents. The Haverhill, Georgetown & Danvers Street Railway began service in 1896. As in Ipswich, passengers would have to disembark and walk to the center of Georgetown because the railroad commission would not allow the streetcars to cross the track. This inconvenience was eventually corrected by building a trestle that crossed high over the tracks.

In Georgetown, a trestle was built, allowing the Georgetown-Ipswich trolley to cross the railroad tracks.
The first bridge over the tracks at High Street was built in 1906
The first bridge over the tracks at High Street was built in 1906 to accommodate the trolley from Georgetown. High Street originally went straight (on the left.)
high_st_trolley_crossing
The crossing at High Street before the bridge was built. 
The Georgetown-Ipswich trolley
The Georgetown-Ipswich trolley

The era of the trolley ended as quickly as it came. By 1919 the streets were beginning to fill with Mr. Ford’s Model T’s, and people were no longer willing to wait for a ride.

Trolley tracks on Central Street
Trolley tracks were laid on Central Street, connecting the Essex and Georgetown lines.
Trolley at Market Square
Closed trolley at Market Square
Trolleys unloading at Market Square
Trolleys unloading at Market Square
ipswich_trolley
Open trolleys were used in the summer
Trolley tracks at Market Square
The automotive age brought the end of trolleys in Ipswich, but the tracks stayed around for awhile.
olde_house_trolley_tracks
The old Joseph Lord house on High Street, and trolley tracks. Photo by George Dexter
waters_adeline_george_miriam
The family of Thomas Franklin Waters on County Rd.
1910 trolley map for the North Shore area
1910 trolley map for the North Shore area

Sources:

View more trolleys at Manchester Streetcars and the Seashore Trolley Museum

Trolleys had to contend with people, cows, horses, wagons, and deteriorating tracks. The video below is taken from a trolley on a Boston street, circa 1900.

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