Shepard, Winston, & Company won the contract to build the tunnel and the railroad from South Freeport to the Mississippi River while subcontractors obtained some related jobs.
Shepard, Winston, & Company employed 354 laborers to hand dig the 2,440-foot tunnel.
Construction crews started at the west heading on May 12, 1887 and from the east in July 1887. The "sandhogs" also dug from a 198-foot vertical shaft sunk from the crest of the hill to the center of the tunnel. Crews labored around the clock for almost an entire year to build the tunnel.
The first train to pass through the tunnel was a construction train on January 19, 1888.



the Sign above the Winston Tunnel says
"Absolutly no Admittance without Permission"
the Illinois Department of Natural Resources controls the Tunnel.