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Hiking trails & Routes
United States
Illinois
Cook County
Riverdale

Major Taylor Trail

Hard

3.3

(27)

81

hikers

Major Taylor Trail

06:00

23.9km

20m

Hiking

Embark on the Major Taylor Trail, a challenging 14.8-mile (23.9 km) hike that winds through Chicago's diverse southwest side. Despite its minimal 64 feet (20 metres) of elevation gain, the route is rated difficult due to its length and urban navigation, requiring an estimated 6 hours to complete. You will experience a unique blend of cityscapes and nature, moving from the shaded canopies of Dan Ryan Woods to the open spaces near Whistler Woods. Keep an eye out for the impressive 400-foot-long mural on a bridge over the Little Calumet River, a distinct visual landmark along your journey. This trail offers a deep dive into the city's varied environments.

When planning your hike, be aware that the Major Taylor Trail is mostly paved, ensuring good accessibility, though you might encounter some unpaved sections. Street crossings are common along the route; busier intersections often have traffic lights or stop signs, so always stay alert to your surroundings. Parking is generally available near the various trailheads and access points, making it convenient to start your adventure. Consider an early start to comfortably complete the full distance.

The Major Taylor Trail provides a unique opportunity to explore Chicago's urban fabric alongside its natural preserves. It connects significant green spaces like Dan Ryan Woods and Whistler Woods, offering a continuous path through different ecological zones. This route is notable for its dedication to the legacy of Major Taylor, an African American cycling champion, and serves as an important community asset. You will find yourself traversing tranquil neighborhoods, bustling urban streets, and even industrial areas, showcasing the city's multifaceted character.

Last updated: April 23, 2026

Waypoints

A

Start point

Parking

Get Directions

1

276ย m

Whistler Woods

Highlight โ€ข Forest

Whistler Woods is home to oaks that are 300 years old and hosts a portion of the Major Taylor Trail, a trail that is over 8 miles long.

Tip by

2

5.22ย km

Major Taylor Trail

Highlight (Segment) โ€ข Cycleway

Stretching from Dan Ryan Woods south to Whistler Woods, the Major Taylor Trail offers a diverse route with paved, off-street, and on-street segments managed by the Chicago Park District. Named after Marshall "Major" Taylor, an African-American bicycle racer and civil rights advocate, the trail pays homage to Taylor's exceptional career.

Tip by

3

10.8ย km

Dan Ryan Woods

Highlight โ€ข Forest

Dan Ryan Woods, a beloved family destination on Chicago's South Side, spans 257 acres. Featuring sledding hills, historic aqueducts, fitness stairs, and a mile-long paved loop connecting to the Major Taylor Trail, it offers diverse recreational opportunities. Beyond its recreational appeal, Dan Ryan Woods supports a thriving ecosystem with native plants, a variety of animals, and migratory birds.

Tip by

B

23.9ย km

End point

Parking

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Way Types & Surfaces

Way Types

20.2ย km

3.69ย km

Surfaces

14.0ย km

7.99ย km

1.19ย km

677ย m

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Elevation

Elevation

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

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Weather

Powered by Foreca

Today

Friday 14 August

26ยฐC

21ยฐC

75ย %

Additional weather tips

Max wind speed: 11.0ย km/h

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Frequently Asked Questions

What is the terrain like on the Major Taylor Trail, and how difficult is it?

The trail offers a varied experience, blending urban landscapes with natural stretches. You'll find primarily paved surfaces, making it accessible, though some segments might be unpaved. It's largely flat, but some sections wind through urban streets, requiring awareness of traffic. The difficulty is generally considered accessible, ranging from easy to moderate, suitable for various fitness levels.

What are some notable features or points of interest along the route?

The trail itself is a tribute to Marshall "Major" Taylor, a pioneering African American cyclist. You can see murals depicting his achievements, including one at 1043 W 111th Street and a 400-foot-long mural on a bridge spanning the Little Calumet River. The route also connects significant green spaces like Dan Ryan Woods in the north and Whistler Woods in the south.

Where can I park to access the Major Taylor Trail?

The trail connects several neighborhoods and forest preserves, offering multiple access points. Parking is available at various points along the route, particularly near the connected forest preserves like Dan Ryan Woods and Whistler Woods. Specific parking lots are managed by the Forest Preserves of Cook County.

Is the Major Taylor Trail dog-friendly?

Yes, the trail is generally dog-friendly. However, always ensure your dog is on a leash and that you clean up after them to maintain a pleasant experience for all users.

What is the best time of year to hike the Major Taylor Trail?

The trail can be enjoyed year-round. Spring and fall offer pleasant temperatures and beautiful scenery, especially in the forest preserve sections. Summer is also great, though some parts can be exposed to sun. Winter hiking is possible, but be prepared for colder conditions and potential snow or ice on the paved surfaces.

Do I need a permit or pay an entrance fee for the Major Taylor Trail?

No, there are no permits or entrance fees required to use the Major Taylor Trail itself. It is a public trail managed by the Forest Preserves of Cook County and the City of Chicago.

Is the Major Taylor Trail suitable for beginners or those with limited mobility?

Yes, many sections of the trail are suitable for beginners due to its largely flat and paved surface. The "easy" routes are good for any fitness level. While some urban sections involve street crossings, the overall accessibility makes it a good option for those new to hiking or seeking a less strenuous outing.

Does the Major Taylor Trail connect with other paths?

Yes, the route primarily follows the Major Taylor Bicycle Trail for a significant portion. It also includes sections of Vincennes Avenue, Damen Avenue, 119th Street, Hermitage Avenue, 111th Street, 115th Street, and various segments of the Dan Ryan Black Paved Loop Trail.

Is the Major Taylor Trail a loop or an out-and-back route?

The Major Taylor Trail itself is primarily a linear, multi-use path connecting different areas. While you can create loop routes by combining it with other streets or trails, the main path is an out-and-back experience if you traverse its full length.

How can I access the Major Taylor Trail using public transport?

Given its urban location on Chicago's southwest side, the trail is accessible via various public transportation options. You can check the Chicago Transit Authority (CTA) or Metra schedules for routes that serve the neighborhoods adjacent to the trail, particularly near its northern and southern termini in Dan Ryan Woods and Whistler Woods.

Are there cafes or facilities near the Major Taylor Trail?

As the trail passes through several urban neighborhoods, you'll find various amenities, including cafes, restaurants, and shops, particularly in the more developed sections. It's a good idea to plan your stops or bring your own refreshments, especially when traversing the more natural forest preserve areas.

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