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 Cellars Annual Fall Harvest Festival
Galena Cellars Vineyard & Winery • Sep 26 @ 11AM
Join Galena Cellars as they celebrate the 2026 Harvest! The 16th Annual Fall Harvest & Art Festival will take place at the Galena Cellars Vineyard.
Read more about Galena Cellars Annual Fall Harvest Festival
19th Annual Galena Oktoberfest
Depot Park • Oct 03 @ 11AM
Family Fun, Live Polka Music, Wiener Dog Racing, plus German-style Food and Beer, headline this year's popular Galena event!
Read more about 19th Annual Galena Oktoberfest
Galena Country Fair
Grant Park • Oct 10 – Oct 11 @ 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!
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