2
hikers
01:11
4.22km
90m
Hiking
Hike the 2.6-mile Winston Tunnel Trail in Illinois, exploring a historic railway route through a wild, rewilded landscape to a sealed tunnel
Last updated: February 26, 2026
Waypoints
Start point
Parking
Get Directions
1.37 km
Winston Tunnel State Natural Area
Nature Reserve
4.22 km
End point
Way Types & Surfaces
Way Types
4.20 km
< 100 m
Surfaces
4.19 km
< 100 m
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Elevation
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Weather
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Today
Sunday 17 May
28°C
16°C
78 %
Additional weather tips
Max wind speed: 25.0 km/h
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This route was planned by komoot.
The trail has a designated trailhead, and parking is typically available there. Look for signs indicating the start of the trail near the Winston Tunnel State Natural Area.
Yes, the trail is generally dog-friendly. However, given the potential for steep terrain, muddy sections, and the presence of wildlife like rattlesnakes, it's crucial to keep your dog on a leash and ensure they are comfortable with rugged conditions. Always pack water for your pet.
Spring and fall are often ideal. Spring offers lush greenery and wildflowers, while fall brings vibrant foliage to the Driftless Area. Be aware that spring thaws can make sections of the trail very muddy and swampy, so sturdy waterproof boots are recommended. Summer can be hot and humid, and winter hiking might present icy conditions.
No, there are typically no permits or entrance fees required to access the Winston Tunnel Trail or the Winston Tunnel State Natural Area. It's a public natural area open for enjoyment.
The Winston Tunnel Trail is generally considered a moderate hike. While it's about two miles long, some sections can be steep, strenuous, and potentially dangerous due to uneven ground, rusted steel supports, and rotting timber from its railway past. It might be challenging for very young children or those unaccustomed to rugged terrain. Sturdy hiking boots are highly recommended.
The terrain varies, starting with mostly mowed grass or a 'herd path' that transitions onto old train tracks. It can be dense and overgrown, almost jungle-like, with abundant pines and ferns. You should wear sturdy hiking boots to navigate potentially muddy, uneven, or steep sections. Jeans or long pants are advisable to protect against overgrown brush and potential ticks.
The most significant feature is the historic Winston Tunnel itself, though it's sealed off. You can walk up to its western entrance. The trail winds through the unique 'Driftless Area' with rugged hills and bluffs, offering a chance to see how nature reclaims abandoned infrastructure. Keep an eye out for various wildlife, including birds and potentially rattlesnakes, especially near the tunnel area.
No, the historic Winston Tunnel is sealed off and inaccessible to the public. It was closed due to instability and the presence of rattlesnakes. Hikers can walk up to its western entrance, but entering the tunnel is not permitted and can be dangerous.
Yes, the route also passes through sections of the Grand Illinois Trail - Mississippi Palisades State Park to Lake Le-Aqua-Na State Park and the Mississippi River Trail (Illinois).
While some sources suggest it can be completed in about 1.5 hours, many hikers find it takes up to two hours or even longer than anticipated, especially if you take your time to explore or if conditions are muddy. The total distance is approximately 2.6 miles (4.2 kilometers).
The Winston Tunnel Trail is primarily an out-and-back route. You will hike to the tunnel entrance and then return along the same path.