Winston Tunnel State Natural Area
2641 S. Blackjack Rd., Galena, IL 61036
Hiking & Trails
230 acres for public hunting, hiking, nature viewing and an historic railroad tunnel.
While the tunnel itself has been walled off for years now, the entrance and walk along the tracks is beautiful. The trails are mostly either mowed grass or herd path along the way to the tunnel. Half way through the hike, the path drops right onto the old train tracks and heads to the tunnel.
The Winston Tunnel was built in 1888 for the Minnesota and Northwestern Railroad, a line that ran from Chicago to Minneapolis, Omaha and Kansas City.
This is a two-mile hike over some steep terrain that takes about 2 hours. Add extra time for pictures! Open All Year and pet-friendly.
What's happening nearby...
Galena Country Fair
Grant Park • Oct 11 – Oct 12 @ 10AM
One of Galena's most popular events featuring more than 100 vendors selling a variety of high-quality, original handmade arts, crafts and fine arts!
Read more about Galena Country Fair
Twenty Dirty Hands Self-Guided Pottery Tour
Multiple Locations • Oct 17 – Oct 19 @ 10AM
Join in the 24th edition of the Tri-State region’s only self-guided pottery tour, October 17 - 29, 2025.
Read more about Twenty Dirty Hands Self-Guided Pottery Tour
Other Side of the Anvil
Lawn adjacent to the Stillman Mansion • Oct 18 – Oct 19 @ 10AM
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