On August 25, 1853, the Galena & Chicago Union Railroad – later to become the Chicago & North Western Railroad – entered Freeport. This company was financed by local sales of stock along its route. John Addams (father of Jane Addams) and D.A. Knowlton were instrumental in making sure that enough stock was subscribed to bring the line into Freeport. The road was to continue to Galena; however, in 1851 the Illinois legislature enacted a bill providing for construction of the Illinois Central Railroad. An agreement was entered into under which the Galena and Chicago road would terminate in Freeport, and the Illinois Central would build the line westward to Galena. The Galena & Chicago line terminated in Freeport and never went further west. As long as the Galena & Chicago Road and the Illinois Central ran, they exchanged business in Freeport and used the same station. The station was located on the river bank south of Stephenson Street. The present station house was built in 1890.

In June, 1854, the Illinois Central Railroad line was completed from Freeport to Galena. In 1856, the Illinois Central Railroad line from Freeport to Dixon, LaSalle, Cairo and St. Louis was completed and eventually continued south to New Orleans.

From 1886 to 1888 the Illinois Central continued to expand its lines, and by purchasing the Freeport Malleable Iron Works property and buildings, the I.C. was able to expand its shops and yards. These buildings were located southeast of the ticket station. The yard and shop remained in this location until removed in the 1960s.

In 1887, the Illinois Central ran a line north from Freeport to Madison, Wisconsin. The line ran through Scioto Mills and Red Oak. At Red Oak the Illinois Central built a junction station where the line branched. The northern branch, running through Buena Vista and Orangeville, became known as the Madison branch of the Illinois Central Railroad. This branch is what now constitutes the Jane Addams Trail.

The route closely followed Richland Creek, which has its headwaters just south of Monroe, Wisconsin. The route was chosen for three reasons. First, building a rail line on level ground made good economic sense. Second, the route is a fairly straight north-south path between Monroe and Freeport. And third, the railway was developed to make a profit from transporting passengers and freight so building the line to connect the municipalities along the way was a sound economic decision.

The Richland waterway was ideal for early construction of mills, and several municipalities grew up around these mills. Between the Wisconsin and Illinois state border and Freeport, five mills and resultant towns were established on the banks of the Richland long before the coming of the rail line, and the railroad established stations at four of these five towns.

By 1888 there were three major railroads, with freight houses, shops, yards and station houses, competing in Freeport. The rate wars that occurred in these years resulted in the Illinois Central Railroad building its own line directly from Freeport to Chicago. The Illinois Central now competed directly with the Chicago North Western for the Rockford and Chicago traffic with a shorter and faster line.

Illinois Central was one of the largest employers in Freeport, employing 500 men in the shops to repair and build cars and service locomotives. During peak operations there could be as many as 1,200 people on its local payroll.

In September, 1859, the Racine & Mississippi Railroad – later to become the Chicago, Milwaukee & St. Paul Railroad – entered Freeport. This line ran from Racine to Beloit, and then through Durand, Davis, Rock City and Dakota before entering Freeport. Their final stop was Savanna. Their station and shops were located east of the river on the north side of Stephenson Street between Commercial and North Henderson avenues. This line, with its shops and 24-hour stall roundhouse, helped make Freeport a railroad center in the 1860s. These shops were moved to Savanna in 1891.

By 1890 most villages in Stephenson County had two or three passenger trains a day in each direction, but by the 1940s most of the “locals” had been taken off. In the following two decades each road, one by one, ran its last passenger train.

The Illinois Central started service reduction with the Dodgeville and Madison branch passenger trains; in 1939 ended service south to LaSalle and Clinton on the old charter line, and finally in 1967 discontinued its prestige train, the Land O’ Corn.

Early Illinois Central Passenger Motor Cars by David J. Daisy (Taken from the “Green Diamond” Official Publication of the Illinois Central Historical Society, Issue Number 58, August 2001)

The first non-steam power purchased by the Illinois Central were several gas powered motor cars for passenger service. The Illinois Central assigned number 111 and 112 to a pair of gas powered motor cars built by McKeen Motor Car Company. The first motor car purchased by the Illinois Central was car 111. It was built in September, 1907, with a length of 55 ft. and seating for 57 passengers. As built, motor car 111 was painted a dark green and lettered as Union Pacific 12. At the time McKeen Motor Car Company was a subsidiary of the Union Pacific. In addition to McKeen Motor Car Company, the Union Pacific also owned a large block of Illinois Central stock which most likely played a big part in the Illinois Central purchasing the car. In January, 1908, Union Pacific 14 was assigned to passenger service on the branch line between Freeport, Illinois, and Madison, Wisconsin. This McKeen car was purchased officially in November of that year and relettered for the Illinois Central as 111. Motor car 111, during the years it ran between Freeport and Madison, was given the nickname of “Maude.” Sometime around World War 1, car 111 was retired.

The Irish
In Freeport, the Irish have been prominent in police departments, fire departments and railroading. Generations of Stephenson County and Freeport Irish families can trace their immigration back to the potato famine of the late 1840s. During this time frame, most came to Stephenson County and Freeport for the railroads. The Illinois Central, Chicago & North Western, and Chicago & Milwaukee were all laying line in Stephenson Country and Freeport in the early 1850s. After the lines were laid most of these families stayed in the area to work for the railroad as yard men, engineers, etc., or to farm. Those that farmed were fortunate. When they began clearing the land of trees, they found that they could sell this lumber to the railroads for large profits. These ties were used to replace the originals that the Irish had laid.

The Italians
For the first generation of Italians in Freeport the main employers were the railroads. Many “came up the railroad” from New Orleans, where they were already working for the Illinois Central, when it was known that there were jobs extending track and working in the huge shops which repaired and built cars. These families tended to settle near the railroad shops on Winneshiek, Wright, Miami, Madison, Float and Iroquois Streets. They obtained permission from the Illinois Central to raise vegetables along the railroad right of way. Fathers and sons tended the gardens and brought the produce home for wives to preserve or peddle. The gardens proved to be a life saver during the Illinois Central strike-lockout in the 1920s. For years the local Italian families held an annual Mardi Gras Ball attended by as many as 200 couples in elaborate costumes.

African Americans
African American railroad workers were not, as a rule, generational residents of Freeport or Stephenson County. They also “came up the railroad” from the south where they were already employed by the Illinois Central.