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Routes
Road cycling routes
United States
Illinois
Cook County
Midlothian

Old Plank Road, Cal-Sag & Centennial Trail Loop

Routes
Road cycling routes
United States
Illinois
Cook County
Midlothian

Old Plank Road, Cal-Sag & Centennial Trail Loop

Moderate

4.9

(7438)

10,580

riders

Old Plank Road, Cal-Sag & Centennial Trail Loop

04:29

112km

230m

Road cycling

This 69.3-mile (111.5 km) moderate road cycling loop combines the Old Plank Road, Cal-Sag, and Centennial Trails for a diverse ride.

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Joe Orr Woods

Halsted Woods

Woodrow Wilson Woods

Indian Hill Woods

Romeoville Prairie Nature Preserve

Waypoints

A

Start point

Train Station

Get Directions

1

16.0 km

Glenwood Woods

Highlight • Forest

The easiest way to explore Greenwood Woods Park is to walk/ride part or all of Thorn Creek Red Paved: a journey into the metropolitan woods!

Tip by

2

31.3 km

Old Plank Road Trail

Highlight (Segment) • Cycleway

This is a 22-mile (35 km) paved trail through Sheboygan County. You ride past lots of wildlife en route. Keep your eyes peeled for bald eagles and beavers along the river.

Tip by

3

43.3 km

Hickory Creek Forest

Highlight • Forest

This beautiful preserve protects forests, prairie, savanna and wetland habitats. You'll find lots of wildlife here such as woodpeckers. In winter, trails are open for cross-country and skiing. There are …

Tip by

4

77.6 km

Centennial Trail

Highlight (Segment) • Cycleway

This is a paved 30-mile (48 km) bike trail that traces a former railway line through Snohomish and Skagit county. You ride through beautiful scenery – green farmland, creeks and …

Tip by

5

91.5 km

Saganashkee Slough

Highlight • Lake

Saganashkee Slough is surrounded by pristine woodlands that hold some of the most untouched nature in the county. You can hike through the area and also take a canoe or …

Tip by

B

112 km

End point

Train Station

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Way Types & Surfaces

Way Types

76.3 km

26.4 km

5.53 km

3.15 km

219 m

Surfaces

91.0 km

20.6 km

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Elevation

Elevation

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

Highest point (230 m)

Lowest point (180 m)

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Weather

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Today

Wednesday 27 May

28°C

16°C

0 %

Additional weather tips

Max wind speed: 21.0 km/h

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This route was planned by komoot.

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Frequently Asked Questions

How long does it take to cycle this loop?

The full loop is about 111.5 kilometers (69 miles) long. For a race bike, it typically takes around 4.5 hours to complete, depending on your pace and how often you stop.

What is the overall difficulty of the Old Plank Road, Cal-Sag & Centennial Trail Loop?

This loop is generally considered to be of moderate difficulty for road cyclists. While the terrain is mostly flat, the significant distance and varied surface conditions, especially on the Old Plank Road Trail, contribute to its moderate rating.

Is this trail suitable for beginner cyclists?

While the trails themselves are largely flat and paved, the full loop is quite long (69 miles). Beginners might find the distance challenging. However, you can easily ride shorter sections of the Old Plank Road Trail, Centennial Trail, or Cal-Sag Trail for an easier experience.

What are the surface conditions like on the loop?

The loop is entirely paved, but surface quality varies. The Centennial Trail is known for its very nice paving and good condition. However, sections of the Old Plank Road Trail are in serious need of resurfacing, with numerous cracks that can make for a bumpy ride. Be prepared for some rougher patches, especially if you're on a road bike.

Where can I park to access the loop?

There are numerous parking areas along each of the individual trails that make up this loop. For example, the Old Plank Road Trail passes through several towns like Frankfort and Matteson with access points. The Cal-Sag Trail has parking, including east of the 86th Avenue area. The Centennial Trail also offers various access points. Check local forest preserve district websites for specific trailhead parking locations.

Is the Old Plank Road, Cal-Sag & Centennial Trail Loop dog-friendly?

Yes, dogs are generally allowed on these trails, but they must be kept on a leash at all times. Please remember to clean up after your pet to keep the trails enjoyable for everyone.

What is the best time of year to cycle this route?

Spring and fall are ideal for cycling this loop, offering pleasant temperatures and beautiful scenery. Summer can be enjoyable, but be prepared for heat and humidity. The 'cathedral of trees' sections on the Old Plank Road Trail provide good shade during warmer months.

Are there any challenging sections or things to be aware of?

Yes, there are a few things to note. The Old Plank Road Trail has 31 road crossings, many of which are 'blind crossings' that can interrupt your momentum and require extra caution. Also, some segments of the Cal-Sag Trail are still incomplete, which might require minor detours to maintain a seamless loop experience.

What kind of scenery can I expect along the way?

The loop offers a diverse range of scenery. You'll ride through shaded 'cathedrals of trees' and past towns on the Old Plank Road Trail. The Cal-Sag Trail follows the Cal-Sag Channel and Calumet River, with natural areas, forest preserves like Glenwood Woods and Hickory Creek Forest, and views of Saganashkee Slough. The Centennial Trail features prairies, woods, and views along the Des Plaines River and Chicago Sanitary and Ship Canal.

Do I need a permit or pay an entrance fee to use these trails?

No, you do not need a permit or have to pay an entrance fee to access and cycle on the Old Plank Road, Cal-Sag, or Centennial Trails. They are publicly accessible multi-use trails.

Does this loop connect to other trails?

Yes, this loop is part of a larger interconnected trail system. The Old Plank Road Trail connects to the Hickory Creek Bikeway and the Thorn Creek Trail system, and is part of the Grand Illinois Trail and American Discovery Trail. The Cal-Sag Trail connects directly with the Centennial Trail and the John Husar I&M Canal Trail. The Centennial Trail also connects to the I&M Canal Trail.

Nearby routes

Moderate

4.0

20

Cal-Sag Trail and Centennial Trail

04:15h

96.3km

150m

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