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Cycling routes
United States
Illinois
Cook County

Winnetka

The best cycling routes around Winnetka

4.5

(165)

967

riders

73

rides

Touring cycling routes around Winnetka, Illinois, benefit from the village's location along Lake Michigan's North Shore. The area features a landscape characterized by tree-lined streets, sandy beaches, and numerous parks. Key natural features include the expansive Skokie Lagoons network and sections of the Forest Preserves of Cook County, offering varied terrain for cycling. The region provides a mix of paved and unpaved trails suitable for different cycling preferences.

Best touring cycling routes around Winnetka

  • The most popular touring cycling route…

Last updated: May 13, 2026

5.0

(14)

44

riders

#1.

North Branch Black Paved Trail – North Branch Trail loop from Hubbard Woods

27.2km

01:33

50m

50m

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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Easy

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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5.0

(1)

23

riders

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

Easy
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Tips from the Community

Jamie S.
September 3, 2024, Skokie Lagoon No. 3

From this grassy spot you get a lovely view of Skokie Lagoon No. 3. This lagoon is part of the Skokie Lagoons nature preserve, located in Glencoe and Winnetka, Illinois. This lagoon is one of seven interconnected lagoons spanning 190 acres, managed by the Forest Preserve District of Cook County. The lagoons were created by the Civilian Conservation Corps between 1933 and 1940, transforming a marshy area into the artificial lagoons seen today. On hot days you might see folks fishing, and kayaking. This is a great spot to rest and relax before continuing on your ride.

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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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Amy
February 13, 2024, Rosewood Beach

This is a wonderful beach in Chicago where you can swim and relax in nature. Check out the swimming times before you arrive here: pdhp.org/rosewood-beach The beach has a nature cove for ecological programs too.

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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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Alex
February 13, 2024, Skokie Lagoon 5

Nestled within the north and central sections of Skokie Lagoons, this lagoon is encircled by trails from the North Branch Trail System, providing cyclists with a tranquil and picturesque route. Enjoy a peaceful ride amidst the scenic trails that wind around the lagoon, offering a serene cycling experience.

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Kit P
February 13, 2024, Skokie Lagoons

Skokie Lagoons are a beautiful lagoon system to the north of Chicago. A nature preserve, the area is rich in plant, bird and animal life, so there are plenty of opportunities to see everything from green herons to snapping turtles. There's a great cycle trail around the lagoons on the North Branch Trail, and lots of places where you can stop for a picnic and enjoy the views.

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Frequently Asked Questions

How many touring cycling routes are available in Winnetka?

Winnetka offers a wide variety of touring cycling routes, with over 70 routes available for exploration. These routes cater to different preferences, ranging from easy rides to more moderate challenges.

What kind of terrain can I expect on Winnetka's cycling paths?

Winnetka's cycling paths offer a mix of terrain. You'll find both paved and unpaved sections, winding through tree-lined streets, along the serene Skokie Lagoons, and within the expansive Forest Preserves of Cook County. The region's landscape along Lake Michigan's North Shore provides a picturesque backdrop for your rides.

Are there any family-friendly touring cycling routes in Winnetka?

Yes, Winnetka is well-suited for family cycling. Many of the routes are classified as easy, making them ideal for all ages. The North Branch Black Paved Trail – North Branch Trail loop from Northfield, for example, is an easy 11.7 km ride that takes just over 30 minutes, perfect for a family outing. The Green Bay Trail, a popular car-free option, also runs through Winnetka and is excellent for families.

What are some scenic viewpoints or natural attractions along the cycling routes?

Winnetka's routes offer numerous scenic spots. You can enjoy views of Lake Michigan from various beaches like Lee Street Beach and Burnham Shores Park. The Skokie Lagoons provide a serene environment for birdwatching and enjoying nature. The Harms Woods Preserve also offers beautiful natural settings along its trails.

Are there any circular touring cycling routes in Winnetka?

Yes, many of Winnetka's touring cycling routes are designed as loops, allowing you to start and end at the same point. A great example is the Skokie Lagoons – Harms Woods Preserve loop from Kenilworth, an easy 31.8 km route that takes you through diverse natural landscapes.

What do other touring cyclists say about the routes in Winnetka?

The touring cycling routes around Winnetka are highly regarded by the komoot community, boasting an average rating of 4.7 out of 5 stars from over 120 reviews. Cyclists often praise the peaceful wooded areas, the scenic beauty of the Skokie Lagoons, and the well-maintained paths that make for enjoyable rides.

Are there any challenging touring cycling routes for experienced riders?

While many routes are easy, Winnetka does offer some moderate options for those seeking a bit more challenge. For instance, the Skokie Lagoon 5 – North Branch Black Paved Trail loop from Winnetka is a moderate 36.0 km route that includes more elevation changes, providing a more demanding experience.

What are some interesting landmarks or places to explore near the cycling paths?

Beyond the natural beauty, you can explore several landmarks. The stunning BahΓ‘ΚΌΓ­ House of Worship Wilmette is a notable architectural site. The Grosse Point Lighthouse offers historical charm, and the Skokie Northshore Sculpture Park provides an outdoor art experience along the trails.

Is it possible to access Winnetka's bike paths using public transport?

Winnetka is part of the Chicago metropolitan area, and public transportation options like Metra commuter rail serve the village. You can plan your journey to reach various starting points for the bike paths, such as those near the Green Bay Trail or the North Branch Trail system, which are accessible from different parts of the village.

Where can I park my car when visiting Winnetka's bike trails?

Parking is generally available at various access points to the trails and parks in Winnetka. Many parks, including those managed by the Winnetka Park District and the Forest Preserves of Cook County, offer designated parking areas. For specific routes, it's advisable to check the starting point for available parking facilities.

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

The best time for touring cycling in Winnetka is typically during the spring, summer, and fall months. These seasons offer pleasant temperatures and vibrant natural scenery, from blooming flowers in spring to colorful foliage in autumn. Summer provides warm weather ideal for combining cycling with visits to the nearby Lake Michigan beaches.

Are there any routes that specifically highlight the Skokie Lagoons?

Yes, the Skokie Lagoons are a central feature of many touring cycling routes in Winnetka. The North Branch Trail – North Branch Black Paved Trail loop from Kenilworth offers scenic views along the North Branch Trail system, which winds around the lagoons. Another excellent option is the Skokie Lagoons – Harms Woods Preserve loop from Kenilworth, which directly leads through this expansive network of lagoons.

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