The
Danbury and Norwalk Railroad opened the line in late February 1852, with the official opening on March 1. Charles Cannon of Cannondale was the subcontractor who helped build the route through Wilton. The train cost passengers 30 cents to go to South Norwalk and 50 cents to Danbury at a time when the day's wages of a laborer might not be a dollar. Two trains made the trip up and down the line each day. In the first few years, a freshet and a flood from the
Norwalk River twice shut down the line for repairs. The station made travel suddenly much quicker than stagecoach transportation. After a few years, when speeds picked up a bit on the line, it took 28 minutes to reach South Norwalk. In its early years, the line had no more than 390 passengers a day using the service, and an average of 34 passengers per train. L. Peter Cornwall, a railroad historian, estimated that perhaps no more than a dozen people used Cannondale in its early years. Although there may have only been a flag stop (in which passengers or railroad employees raised a flag if they needed the train to stop), by 1856 it was a regular stopping point for all trains, and the stop was originally called '''Cannon's
. In the early 1870s the station was no longer listed and was probably a flag stop. In the 1890s it was again listed as a station, now called Cannon
. Just before World War I, the station name was changed to Cannondale'''. ==Station layout==