4.5
(15)
152
hikers
32
hikes
Hiking around Highwood offers access to a network of trails primarily characterized by flat terrain and minimal elevation changes. The region features a mix of forest preserves, open natural areas, and wetland ecosystems, providing accessible outdoor experiences. These trails often follow established paths through local woodlands and restored prairies.
Last updated: October 18, 2026
3.0
(1)
2
hikers
3.82km
00:58
10m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
1.51km
00:23
0m
0m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

1.99km
00:31
20m
20m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
15
hikers
3.76km
00:59
30m
30m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
2
hikers
22.4km
05:46
100m
110m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Popular around Highwood
This bronze sculpture is a tribute to General Sheridan, a Civil War general. It depicts him on a horse during Battle of Five Forks in April 1865.
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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.
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Enjoy breathtaking views of Lake Michigan at Fort Sheridan Beach lookout. This vantage point offers a perfect lookout spot, showcasing the beauty of the lake. If the beach beckons, worry not, as easy access awaits from this location.
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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 wooded bluffs, the beach boasts a unique Interpretive Center, along with amenities like concessions, restrooms, and a guard building connected by a charming boardwalk.
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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, and Lake Bluff, the trail is adorned with charming homes, community parks, and convenient amenities. Given its proximity to Lake Michigan, you can opt for shorter on-road side trips to savor beachfront views.
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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 Sheridan to admire this iconic sculpture, commemorating a key figure in American history.
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Fort Sheridan Forest Preserve, an Illinois gem, combines history and nature. Amidst remnants of the former military base, discover scenic trails, woodlands, and Lake Michigan's shoreline for a diverse outdoor experience.
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Highwood offers a diverse network of over 30 hiking trails. These routes primarily feature flat terrain and minimal elevation changes, making them accessible for various activity levels.
Yes, Highwood is well-suited for easy hikes, with 25 of the available routes classified as easy. Many trails wind through local woodlands and restored prairies, providing gentle walking experiences. For example, the Red trails is an easy 2.4-mile (3.8 km) route.
The duration of hikes in Highwood varies, but many popular trails can be completed within an hour or two. For instance, the Prairie Wolf Slough is an easy 0.9-mile (1.5 km) path that takes approximately 20-25 minutes, while the Openlands Open Space trail is 1.2 miles (2.0 km) and typically takes around 30 minutes.
Absolutely. The predominantly flat terrain and numerous easy trails in Highwood make it an excellent destination for family-friendly hikes. Many routes pass through forest preserves and open natural areas, offering pleasant and manageable walks for all ages.
Many trails in the Highwood area, particularly those within the Lake County Forest Preserves, are dog-friendly, often requiring dogs to be on a leash. It's always a good idea to check specific trail regulations before heading out.
While Highwood is known for its accessible, flatter trails, there is at least one route classified as difficult among the 33 available. For those seeking a longer, moderately challenging experience, the Skokie Valley Trail offers a 10.1-mile (16.3 km) path with some elevation changes.
Highwood's trails are enjoyable throughout the year. Spring brings blooming wildflowers, summer offers lush greenery, and autumn showcases vibrant fall foliage. Even winter can be beautiful for hiking, especially after a fresh snowfall, though conditions may vary.
Yes, Highwood's trails offer views of diverse natural settings. You can explore wetland ecosystems, as seen on the Prairie Wolf Slough trail, or enjoy the restored natural areas of Openlands Open Space. Nearby attractions include various lakes like Skokie Lagoon No. 3 and the MacArthur Woods Forest Preserve.
Yes, many of Highwood's trails are designed as loops, offering convenient circular routes. An example is the Fort Sheridan Birding Trail Loop, which allows hikers to start and end at the same point while exploring the area.
The hiking experience in Highwood is highly rated by the komoot community, with an average score of 4.3 stars from 9 reviews. Hikers often praise the accessibility of the trails, the peaceful natural settings of the forest preserves, and the well-maintained paths that make for enjoyable walks.
Highwood is served by Metra's Union Pacific North Line, which provides commuter rail service to Chicago and other northern suburbs. Some trailheads, particularly those along the Skokie Valley Trail, may be accessible via public transport or a short walk from train stations, making it possible to reach certain hiking areas without a car.
Beyond the trails, Highwood and its surroundings offer several points of interest. You can visit the MacArthur Woods Forest Preserve, or explore the various Half Day Forest Preserve Ponds. The area also features parts of the North Branch Trail, which extends through different natural areas.


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