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Hikes
United States
Illinois
Cook County

Winnetka

The best walks and hikes around Winnetka

5.0

(3)

182

hikers

77

hikes

Hiking around Winnetka, Illinois, features diverse landscapes within the Forest Preserves of Cook County, offering extensive outdoor opportunities. The region is characterized by a network of lagoons, such as the Skokie Lagoons, and well-maintained trails like the Green Bay Trail. These natural areas provide varied terrain for walking and hiking, from paved paths to unpaved woodland routes.

Best hiking trails around Winnetka

  • The most popular hiking route is Harms Woods West loop โ€” Harms Woods Nature Preserve, a 2.5 miles (4.0 km) trail that takes 1 hour 1 minute to complete. This easy route explores the natural setting of Harms Woods.
  • Another top favourite among local hikers is South Skokie Lagoons loop via North Branch Yellow Unpaved Trail โ€” Skokie, an easy 3.5 miles (5.6 km) path. This trail offers views of the Skokie Lagoons along an unpaved surface.
  • Local hikers also love the Watersmeet Woods & Skokie Lagoons via North Branch Yellow Unpaved Trail โ€” Skokie, a 5.7 miles (9.2 km) trail leading through Watersmeet Woods and along the Skokie Lagoons, often completed in about 2 hours 19 minutes.
  • Hiking around Winnetka is defined by extensive forest preserves, serene lagoons, and dedicated multi-use trails like the Green Bay Trail. The network offers options for different ability levels, from easy walks to moderate hikes.
  • The routes in Winnetka are highly rated by the komoot community with an average score of 5.0 stars from a few reviews. More than 100 hikers have used komoot to explore Winnetka's varied terrain.

Last updated: May 3, 2026

3

hikers

#1.

North Branch Trail: Skokie Lagoons Loop

20.5km

05:10

30m

30m

Hike the 12.8-mile North Branch Trail: Skokie Lagoons Loop, a difficult route with 83 feet of elevation gain, exploring scenic lagoons and w

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Hard

1

hikers

Hike the easy 2.3-mile Skokie Lagoons Inner Trail, a peaceful loop through forestland with views of lagoons and abundant wildlife.

Easy
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Hike the easy 2.3-mile North Branch Red Paved Trail through Cook County's forest preserves, following the Chicago River and spotting wildlif

Easy

11.3km

02:51

10m

30m

Hike the moderate 7.0-mile Green Bay Trail, a family-friendly path offering urban and natural scenery along Chicago's North Shore.

Moderate

3.41km

00:52

20m

0m

Hike the easy 2.1-mile North Branch Trail through Cook County Forest Preserves, featuring river views and wildlife sightings.

Easy
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Popular around Winnetka

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Tips from the Community

maniboyflex
June 20, 2025, Shelton Park

A small, family-friendly park along the Green Bay Trail thatโ€™s a good place to stop and recharge. It has shaded grassy areasโ€”perfect for a quick break.

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This forested area sits just south of the Skokie Lagoons, with the North Branch Paved Yellow Trail running alongside the Skokie River. Itโ€™s a great place to ride with a fresh breeze and plenty of shade. You can follow the path all the way to Watersmeet Woods.

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The southern portion of Skokie Lagoons is where the North Branch Paved Red Trail runs through a shaded area alongside the Skokie River West Ditchโ€”a refreshing and less busy stretch to ride near the lagoons.

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Hubbard Woods Park is a nice, small green space along the Green Bay Trail. It is a good place to stop for a quick break on a bench in the park.

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Giuro
April 12, 2024, Skokie Lagoon 5

The trails surrounding Skokie Lagoon are smoothly paved and include gentle hills. Truly a lovely path two steps away from the Chicago Botanic Gardens!

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Giuro
April 12, 2024, Skokie Lagoon 4

The trails surrounding Skokie Lagoon are smoothly paved and include gentle hills. Truly a lovely path two steps away from the Chicago Botanic Gardens!

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If you are biking along the North Branch Red Paved Trail or the dirt horse trail that follows the Skokie River, you'll pass through a bunch of different parks and preserves. The Watersmeet Woods is one of those natural preserves that the trails pass through.

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Alex
February 13, 2024, Skokie Lagoon 4

The views of the lagoon are lovely, giving a chance to enjoy a peaceful moment away from traffic and noise of the city. There are picnic benches here if you would like to take a break.

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Frequently Asked Questions

How many hiking trails are available in Winnetka?

Winnetka offers a wide selection of outdoor experiences, with over 50 hiking routes available. These trails vary in length and difficulty, providing options for different preferences and fitness levels within the region's diverse landscapes.

Are there easy hiking trails suitable for beginners in Winnetka?

Yes, Winnetka is very accommodating for beginners, with 48 out of 57 routes classified as easy. Many of these trails are well-maintained and offer gentle terrain. A great option for an easy walk is the South Skokie Lagoons loop via North Branch Yellow Unpaved Trail, which provides scenic views along an unpaved surface.

Are there any family-friendly hiking options in Winnetka?

Absolutely. Winnetka's extensive network of parks and forest preserves, including those managed by the Winnetka Park District, offers many family-friendly paths. These often feature accessible terrain and opportunities for nature exploration. The Chicago Botanical Gardens loop is a particularly pleasant and easy option for families.

Are dogs allowed on hiking trails in Winnetka?

Many trails within the Forest Preserves of Cook County, which encompass much of Winnetka's hiking areas, are dog-friendly. It's generally recommended to keep dogs on a leash and to check specific park regulations before heading out. The unpaved sections of trails around the Skokie Lagoons are popular choices for walks with canine companions.

Are there circular hiking routes in Winnetka?

Yes, many of Winnetka's trails are designed as loops, allowing for a continuous journey without retracing your steps. For example, the Harms Woods West loop is a popular circular route that explores the natural setting of Harms Woods Nature Preserve.

What interesting landmarks or natural features can I see along Winnetka's hiking trails?

Winnetka's trails offer access to several notable natural and man-made attractions. You can explore the serene Skokie Lagoons, a significant natural feature ideal for birdwatching. The Harms Woods Preserve provides a beautiful forest setting. Additionally, the Green Bay Trail offers glimpses of Lake Michigan and passes through charming North Shore towns.

Is parking available at the trailheads in Winnetka?

Yes, parking is generally available at various access points for Winnetka's hiking trails, particularly within the Forest Preserves of Cook County and near popular trailheads like those for the Green Bay Trail. These areas are designed to accommodate visitors, making it convenient to start your hike.

Can I reach Winnetka's hiking trails using public transport?

Yes, some trails in Winnetka are accessible via public transport. The Green Bay Trail, for instance, parallels the Metra commuter line, making it convenient for those traveling by train. Checking local Metra schedules and bus routes can help you plan your access to other trailheads.

What is the best time of year to go hiking in Winnetka?

Winnetka offers enjoyable hiking experiences throughout the year. Spring brings blooming wildflowers, while autumn showcases vibrant fall foliage. Summer is ideal for longer days and warmer weather, and even winter hiking can be beautiful, especially after a fresh snowfall, offering a peaceful, serene landscape.

What kind of wildlife can I expect to see while hiking in Winnetka?

The extensive natural areas around Winnetka, particularly the Skokie Lagoons and the Forest Preserves of Cook County, are home to diverse wildlife. Hikers often spot various bird species, including waterfowl and raptors, as well as small mammals like deer, foxes, and squirrels. The lagoons are also rich in aquatic life.

Are there any moderate hiking trails in Winnetka for more experienced hikers?

While Winnetka is known for its easy trails, there are options for those seeking a bit more challenge. The region offers 8 moderate routes. An example is the Watersmeet Woods & Skokie Lagoons via North Branch Yellow Unpaved Trail, which is a longer route leading through varied terrain.

What do other hikers enjoy most about hiking in Winnetka?

The hiking experiences in Winnetka are highly rated by the komoot community, with an average score of 5.0 stars. Reviewers often praise the serene natural settings, the well-maintained paths, and the diverse landscapes that range from tranquil lagoons to peaceful woodlands. The accessibility and variety of trails are also frequently highlighted.

Most popular routes around Winnetka

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