In 1852, the Illinois Central Railroad surveyed a track route through Cumberland County as part of the federal act to build a railroad through Illinois. The route was to connect Mattoon (25 miles northwest) with Grayville (85 miles southeast), located on the Wabash River.  A lack of funding and the onset of the Civil War caused construction to be delayed until 1872. 

Meanwhile, the St. Louis, Vandalia, and Terre Haute Railroad (known as the Vandalia Line) was completed in 1868, making it the first actual railroad to pass through Greenup. Two years later the village board levied taxes and donated $1000 for the purpose of constructing a modest depot, the one that exists today. The depot was modeled in the Victorian style with a wide overhang and gingerbread trim.  A wooden passenger platform and a bay window were built in front of the depot so that a telegraph operator could sit at his desk and see both directions along the track.  A second story served as the living quarters for the stationmaster. The quarters were rather modest, consisting of a family room, kitchen, and two bedrooms. A public outhouse was located near the depot.

In 1872, the Grayville and Mattoon Railroad (later to become part of the Illinois Central) came through Greenup and crossed the Vandalia Line, about ½ mile southwest of where the depot presently stands. Mergers extended the line between Peoria, Decatur, and Evansville in 1890. The railroad was called the P, D & E, and served as a major north-south thoroughfare, crossing the Wabash River just south of Grayville.  The Illinois Central Railroad absorbed all P, D & E track rights in 1900, with the IC maintaining ownership until 1983, when the line was abandoned and salvaged.  Today, only the old IC roadbed remains, with barely a telltale sign that a railroad ever existed.   What is left of the roadbed can still be seen and is located about ¾ of a mile west of the depot at the bottom of the hill.

The Pennsylvania Railroad, an eastern conglomerate connecting New York City with St. Louis, absorbed the Vandalia Line in 1896.  Pennsy’s Greenup depot became the hub of activity as many passenger, freight, mail, and milk trains stopped to exchange cargo.  A daily newspaper stand was located at the station, and a horse-drawn taxi regularly escorted passengers between the depot and the old Barbour Inn, later known as the Conzet Hotel, (located at the northeast corner where the depot parking lot is today). Fare to any part of the village was 15 cents; a round trip was 25 cents.

Many famous people came through the area, including several U.S. Presidents and numerous millionaires. One story is told of John Jacob Astor, then among the richest men in America, who stopped in Greenup perhaps to change trains and to stretch his legs.  It was said that Astor bought an expensive cigar and lounged around the station with his personal porter. A shoeshine boy named Jimmy Phelps shined his shoes and received a thirty-cent tip (for a nickel shine). This was a lot of money for a boy in those days. . . the story even making the newspapers!  The tale became legend when Mr. Astor perished with the sinking of the Titanic in 1912.

After a train wreck occurred near the Penn-IC crossing in the early-1920s, the Pennsylvania Railroad built an elevated track over the Illinois Central in 1927.  Around that same time, a fire destroyed the smaller Illinois Central depot located a few hundred yards away.  Therein, an agreement was made between the two railroads which called for the relocation of the Pennsylvania depot some 200 yards north on the Illinois Central line. The depot was set upon a new foundation, enlarged with a 15-foot extension to the baggage room, with an indoor restroom being added.  Both the Pennsylvania and Illinois Central railroads used the depot; christening it Greenup Union Station. The downstairs was configured into a waiting room, ticket and telegraphy office, and freight room. . .  the same as appears today.

Between the years 1911 and 1930, a well-ridden but short train consisting of a locomotive, tender, two passenger cars, and a caboose, regularly departed Greenup at 7:00 AM, headed east to Terre Haute and Indianapolis and returned to Greenup at 7:00 PM.  The train was called “Bob” or “the Bob Train” and was frequently used by locals who wished to shop in the larger cities.  Unfortunately, the Great Depression not only caused a loss of passenger revenue for both the IC and Pennsylvania railroads, but saw the demise of “Bob”. Passenger service again picked up during the bustling years of World War II. Rider ship peaked in 1945, and then quickly subsided in the postwar years as automobiles replaced rail transportation.  Ticket sales plummeted and passenger traffic ceased, first on the Pennsylvania, then on the Illinois Central railroad.  Although passenger service ended in Greenup during the late 1940s, the depot was maintained for freight and Railroad Express Agency delivery. The doors were locked for the last time on March 7, 1967 when Bill Kent, Illinois Central depot agent and telegrapher, entered retirement.

After the occurrence of some minor vandalism, the Illinois Central Railroad sold the depot to the Cumberland County Historical Society for $25 in 1973. The depot was moved to Haughton Park on July 17 of that year where it remained until October 15, 1992, when it was moved to its present location.   The Depot has been renovated by the Historical Society to serve as a train museum.