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Routes
Hiking trails & Routes
Lake County
Highland Park

Fort Sheridan and Green Bay Trail Loop

Routes
Hiking trails & Routes
Lake County
Highland Park

Fort Sheridan and Green Bay Trail Loop

Hard

1

hikers

Fort Sheridan and Green Bay Trail Loop

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

A

Start point

Train Station

Get Directions

1

821 m

Green Bay Trail

Highlight (Segment) • Trail

Explore the picturesque Green Bay Trail, a delightful 9-mile route paralleling Chicago's Metra commuter rail line north of the city. Winding through North Shore towns like Kenilworth, Winnetka, Highland Park, …

Tip by

2

6.96 km

Rosewood Beach

Highlight • Beach

Experience the allure of Rosewood Beach, a nationally acclaimed destination offering diverse amenities. Discover a nature cove for ecological programs, a guarded swimming beach, and a recreation beach. Nestled against …

Tip by

3

11.5 km

Explore Park Avenue Boating & Fishing Beach, equipped with a concrete ramp and sand launching ramp, complemented by two parking lots and three boat storage facilities. Enjoy scenic views, especially during sailing practice.

Tip by

4

17.5 km

The statue captures Sheridan astride his mount "Rienzi," inspiring his troops during the pivotal Battle of Five Forks in April 1865, a symbol of his leadership and victory. Visit Fort …

Tip by

B

22.4 km

End point

Train Station

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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

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

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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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Frequently Asked Questions

Where can I park to access the Fort Sheridan and Green Bay Trail Loop?

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.

Is the Fort Sheridan and Green Bay Trail Loop dog-friendly?

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.

What is the best time of year to hike this loop?

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.

Are there any permits or entrance fees required for the Fort Sheridan Forest Preserve?

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.

What is the difficulty and terrain like on this loop?

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.

How long does it typically take to complete the Fort Sheridan and Green Bay Trail Loop?

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.

What kind of scenery and landmarks can I expect to see along the way?

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.

What wildlife might I encounter on the trail?

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.

Does this loop connect to other trails?

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.

Are there any specific historical sites or educational opportunities along the route?

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.

Are there cafes or restaurants nearby for post-hike refreshments?

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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