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...
18th Annual Galena Oktoberfest
Depot Park • Oct 04 @ 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 18th Annual Galena Oktoberfest
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 TourYou might also be interested...
Casper Bluff Land & Water Reserve
Galena
Featuring Native American archaeology, this preserve is situated on the scenic Mississippi River Bluffs.
Read more about Casper Bluff Land & Water Reserve
Chestnut Mountain Resort - Outdoor Activities
Galena
Chestnut Mountain is a full-service, 120-unit resort situated eight miles southeast of Galena on a wooded palisade overlooking the Mississippi River. This resort offers an array…
Read more about Chestnut Mountain Resort - Outdoor Activities
Tapley Woods State Natural Area
Galena
A quiet, wooded spot along between Elizabeth and Galena.
Read more about Tapley Woods State Natural Area