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Jo Daviess County

Winston Tunnel Trail

Easy

2

hikers

Winston Tunnel Trail

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

A

Start point

Parking

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1.37 km

Winston Tunnel State Natural Area

Nature Reserve

B

4.22 km

End point

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Way Types & Surfaces

Way Types

4.20 km

< 100 m

Surfaces

4.19 km

< 100 m

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Elevation

Elevation

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Weather

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Today

Sunday 17 May

28°C

16°C

78 %

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Max wind speed: 25.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

Where can I park to access the Winston Tunnel Trail?

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.

Is the Winston Tunnel Trail dog-friendly?

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.

What is the best time of year to hike the Winston Tunnel Trail?

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.

Are there any permits or entrance fees for the Winston Tunnel Trail or Winston Tunnel State Natural Area?

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.

How difficult is the Winston Tunnel Trail, and is it suitable for beginners or families?

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.

What is the terrain like on the trail, and what should I wear?

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.

What notable features or wildlife can I expect to see on the trail?

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.

Can I go inside the Winston Tunnel?

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.

Does the trail intersect other well-known paths?

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).

How long does it typically take to hike the Winston Tunnel Trail?

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).

Is the Winston Tunnel Trail a loop or an out-and-back route?

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.

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