1
hikers
05:46
22.4km
100m
Hiking
Hike the difficult 13.9-mile Fort Sheridan and Green Bay Trail Loop, gaining 344 feet in 5h 46m through diverse landscapes and historical si
Last updated: February 26, 2026
Waypoints
Start point
Train Station
Get Directions
821 m
Highlight (Segment) • Trail
Tip by
6.96 km
Highlight • Beach
Tip by
11.5 km
Highlight • Beach
Tip by
17.5 km
Highlight • Monument
Tip by
22.4 km
End point
Train Station
Way Types & Surfaces
Way Types
8.88 km
7.71 km
3.41 km
1.86 km
505 m
Surfaces
11.7 km
4.22 km
3.87 km
2.51 km
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Elevation
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Weather
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Today
Monday 13 July
33°C
20°C
0 %
Additional weather tips
Max wind speed: 12.0 km/h
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This route was planned by komoot.
You can find parking at various points along the route. For the Fort Sheridan section, parking is available within the Fort Sheridan Forest Preserve. For the Green Bay Trail, there are often parking options in the towns it passes through, such as Highland Park.
Yes, the trails are generally dog-friendly. However, dogs must be kept on a leash at all times. Always remember to clean up after your pet to help keep the trails enjoyable for everyone.
The trail is enjoyable year-round. Spring and summer offer lush greenery and wildflowers, while fall brings beautiful foliage. Winter hiking is also possible, with opportunities for cross-country skiing and snowshoeing, but be prepared for colder conditions.
No, there are no permits or entrance fees required to access the Fort Sheridan Forest Preserve or the Green Bay Trail. Public access is free.
The overall route is rated as difficult due to its length of over 22 km. However, sections vary. The Fort Sheridan trails include rolling hills, bluffs, ravines, woodlands, and savannas, with some paved, natural, or grass paths. The Green Bay Trail is largely flat with alternating asphalt and crushed limestone surfaces, making it generally easy.
This loop is approximately 22.4 km (13.9 miles) long and typically takes around 5 hours and 46 minutes to complete, depending on your pace and stops.
You'll experience diverse scenery, including views of Lake Michigan from a 70-foot bluff, forests, prairies, and savannas. Notable landmarks include the historic General Sheridan Equestrian Statue, the beautiful Rosewood Beach, and the Park Avenue Fishing & Boating Beach. The Green Bay Trail also offers views of charming North Shore towns and their backyards.
The Fort Sheridan Forest Preserve is located on a busy migratory bird flyway, so you have a good chance of seeing hundreds of bird species. The diverse ecosystems also support various other wildlife.
Yes, the Fort Sheridan trails offer connections to other regional trail systems, including the Robert McClory Bike Path and the North Shore Path. The Green Bay Trail itself is a significant regional path that runs parallel to Chicago's Metra commuter rail line.
Absolutely! Fort Sheridan was a former U.S. Army post with rich history. You can find self-guided educational exhibits along the historic parade ground. The preserve also includes a cemetery established in 1889 with gravesites of veterans. The Green Bay Trail itself has historical roots as an ancient trail used by Native Americans and early settlers.
Yes, both the Fort Sheridan area and the towns along the Green Bay Trail (like Highland Park) offer various amenities, including cafes, pubs, and restaurants, perfect for a meal or drink after your hike.
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