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Road cycling around Greenwood offers routes through varied landscapes, characterized by open prairie, river views, and local parklands. The terrain generally features gentle rolling hills, with elevations typically remaining below 250 meters. This area provides accessible road cycling experiences, often following established trails and scenic loops.
Last updated: October 12, 2026
1
riders
56.7km
02:34
220m
220m
The McHenry County Prairie Trail offers a dynamic road cycling experience, transitioning from smooth asphalt to crushed limestone and gravel as you head north. You'll pedal through a mosaic of…
24
riders
57.7km
02:58
190m
190m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

10
riders
38.2km
01:57
140m
140m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
12
riders
35.4km
01:46
120m
120m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
2
riders
53.1km
02:22
240m
240m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Who said the Illinois is flat, well it is flat, however the section of McHenry / Illinois Prairie Rail Trail ad add a bit of variety to the rest of the trail which usually has long drawn out grades of max 2%, here there are 4 short but steep climbs hitting 16% in a very dense Forrest spending a bit of shade on very hot Midwest summers. The trail twists and turns through the forest which does not give one a notice that the climbs are going to be steep.
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The section of trail between McHenry and Edgewood Road is a part of the trail that needs to be resurfaces. It is rideable but there are places where the roots of trees and shrubs have pushed up the surface creating a bit of a rough ride.
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For those riding out from the City of Chicago to the countryside of McHenry County, the Metra Rail Service offers regular and convenient service to Union Station in downtown Chicago. The City of McHenry also has a wide variety of restaurants and bars with outdoor dining facilities to relax, quench a thirsty throat or satisfy a hungry stomach.
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The section of McHenry / Illinois Prairie Rail Trail from Ringwood to McHenry is all asphalted, sometimes smooth, sometimes rough but all in all a decent trail. Suitable for all bicycles but recommend with tyres => 28mm. The trail rolls up and down the countryside, passing McCollum Lake, giving one the opportunity for a quick swim in hot weather. McHenry itself offers many opportunities to eat and drink. The village is very nice clean and many outdoor possibilities to eat and keep an eye on your bike.
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Nice wooden bridge that takes you over the Fox River and into Algonquin. The bridge is part of the Fox River Trail and is completely car-free.
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Nice wooden bridge that takes you over the Fox River and into Algonquin. The bridge is part of the Fox River Trail and is completely car-free.
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Veteran Acres Park shines with upland woods, featuring the captivating Wingate Prairie spanning approximately 30 acres. This vibrant ecosystem hosts a variety of captivating flowers, including asters, blazing stars, and sunflowers. Prairies, situated near the ridge tops and sun-facing slopes, showcase plants adapted to drier conditions. The pine woods, dispersed across both parks, stand as another beloved feature, adding to the allure of Veteran Acres and Wingate Prairie.
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Enjoy cycling through the beautiful Sterne’s Fen Nature Preserve. This place became an Illinois Nature Preserve in 1994 and offers rugged tree lined paths for biking. It's a perfect spot for a ride not too far from Chicago!
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Road cycling routes around Greenwood primarily feature open prairie landscapes, scenic river views, and pleasant parklands. The terrain is generally characterized by gentle rolling hills, with elevations typically remaining below 250 meters, making for accessible and enjoyable rides.
Yes, Greenwood offers routes suitable for beginners. For instance, the Veteran Acres Park – Petersen Park Beach loop from McHenry is an easy 31.1 km (19.3 miles) trail that takes about 1 hour 49 minutes to complete, leading through pleasant park areas.
The road cycling routes in Greenwood vary in length and duration. You can find routes like the Veteran Acres Park – Petersen Park Beach loop from McHenry, which is about 31.1 km (19.3 miles) and takes under 2 hours, up to longer options like the McHenry County Prairie Trail at 56.7 km (35.2 miles), typically completed in around 2 hours 34 minutes.
Yes, many road cycling routes around Greenwood are designed as loops. Examples include the Fox River view – Wooden Bridge Over Fox River loop from McHenry and the Veteran Acres Park – Petersen Park Beach loop from McHenry, offering convenient circular rides.
For scenic rides, consider routes that highlight the region's natural beauty. The McHenry County Prairie Trail offers expansive views across open prairie, while the Fox River view – Wooden Bridge Over Fox River loop from McHenry provides picturesque views along the Fox River, including a distinctive wooden bridge crossing.
The best time for road cycling in Greenwood is generally during the spring, summer, and fall months when the weather is mild and the natural landscapes are vibrant. Summer offers warm conditions ideal for longer rides, while spring and fall provide cooler temperatures and beautiful scenery.
While specific crowd levels can vary, routes that traverse local park areas or less-trafficked prairie trails might offer a quieter experience. Exploring routes during off-peak hours or weekdays can also help you find a more serene ride.
Road cycling routes in Greenwood offer diverse views, ranging from wide-open prairie vistas to tranquil river scenes and pleasant parkland settings. You'll often encounter established trails that showcase the region's natural and accessible beauty.
There are several road cycling routes available around Greenwood, offering a variety of distances and difficulty levels. Komoot currently features at least four distinct road cycling routes in the area.
The road cycling routes around Greenwood are well-regarded by the komoot community, with over 30 road cyclists having explored the area using komoot. Users often praise the varied terrain, which includes prairie trails, river views, and park loops, providing options for different ability levels.
While the region is known for its accessible and moderate routes, experienced cyclists can challenge themselves with longer distances and slightly more elevation gain on routes like the Roadbike loop from Keystone Landing, which covers 52.9 km (32.9 miles) with moderate difficulty.


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