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United States
Illinois
Lake County

Highwood

The best walks and hikes around Highwood

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.

Best hiking trails around Highwood

  • The most popular hiking route is Red trails, a 2.4 miles (3.8 km) trail that takes 58 minutes to complete. This easy route winds through…

Last updated: October 18, 2026

3.0

(1)

2

hikers

#1.

Red trails

3.82km

00:58

10m

20m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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Easy

1

hikers

1.51km

00:23

0m

0m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy
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1.99km

00:31

20m

20m

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

5.0

(1)

15

hikers

Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

Easy

Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.

Hard
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Popular around Highwood

Running Trails around Highwood

Road Cycling Routes around Highwood

Cycling around Highwood

Tips from the Community

Daniel
August 3, 2025, Lake Michigan Beach

not for bikes

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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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oliviakellis
January 20, 2024, Rosewood 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 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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oliviakellis
January 20, 2024, Green Bay 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, 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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Frequently Asked Questions

How many hiking trails are there in Highwood?

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.

Are there many easy hiking trails in Highwood?

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.

What is the typical duration of hikes in Highwood?

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.

Are there family-friendly hiking options in Highwood?

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.

Are dogs allowed on hiking trails in Highwood?

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.

Are there any challenging hiking trails in Highwood?

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.

When is the best time of year to go hiking in Highwood?

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.

Are there scenic viewpoints or natural attractions along Highwood's hiking trails?

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.

Are there circular hiking routes available in Highwood?

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.

What do other hikers enjoy the most about hiking in Highwood?

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.

Is public transport available to access hiking trails in Highwood?

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.

Are there any places to explore near the hiking trails in Highwood?

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.

Most popular routes around Highwood

Easy hikes around Highwood

Most popular attractions around Highwood

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