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 45th Annual Halloween Parade
Main Street, Galena • Oct 25 @ 6:30PM
Join Galena's 45th Annual Halloween Parade & Festival! The largest, longest, and spookiest Parade and Festival in the Tri-State Area!
Read more about Galena 45th Annual Halloween Parade
41st Annual Nouveau Parade & Celebration
Galena Cellars Wine Tasting Room • Nov 21 @ 11AM
Galena Cellars celebrates the release of the 2025 Nouveau wine - The 41st Annual Celebration!
Read more about 41st Annual Nouveau Parade & Celebration
Galena Holiday Kickoff!
Nov 29 @ 5PM
Join in welcoming Santa to town to kick off the holiday season in Galena!
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