4.9
(25)
787
riders
34
rides
Road cycling routes around Highwood, Illinois, are characterized by their passage through preserved forest areas and along river valleys. The region offers an extensive network of managed trails, providing varied terrain for cyclists. These routes often feature flat, paved paths that wind through natural landscapes, including the Des Plaines River Valley. The area's topography is generally gentle, with minimal elevation changes, making it suitable for a range of cycling abilities.
Last updated: May 4, 2026
5.0
(1)
63
riders
43.9km
02:05
140m
140m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
25
riders
23.9km
01:04
80m
80m
Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

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26
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
30
riders
44.6km
02:04
120m
120m
Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
15
riders
24.9km
01:03
50m
50m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Highwood
Fort Sheridan Forest Preserve, an Illinois gem, combines history and nature. Amidst remnants of the former military base, discover scenic trails, woodlands, and Lake Michigan's shoreline for a diverse outdoor experience.
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This is the house where the movie Home Alone was filmed—a fun spot to stop by and remember this iconic film before continuing your ride.
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A small, family-friendly park along the Green Bay Trail that’s a good place to stop and recharge. It has shaded grassy areas—perfect for a quick break.
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This bronze sculpture is a tribute to General Sheridan, a Civil War general. It depicts him on a horse during Battle of Five Forks in April 1865.
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Christ Church has a beautiful courtyard that is open to the public. As this is a place of worship, if you decide to stop to check it out, make sure you are respectful.
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Lake Front Park is a beautiful small park next to Glencoe Beach. There is a large lawn area that is a great spot for a break.
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Founders Park is a small, urban park in Glencoe. It has ball fields, picnic tables, a playground and restrooms.
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You get a lovely view of the Fort Sheridan Pond and the woodland surrounding it. With such a lovely view directly from the relatively quiet road, this is a lovely spot to pass by on your cycle.
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Road cycling routes in Highwood, Illinois, are generally characterized by gentle topography with minimal elevation changes. You'll primarily find flat, paved paths winding through preserved forest areas and along river valleys, such as the Des Plaines River Valley. This makes the area suitable for a wide range of cycling abilities.
There are over 30 road cycling routes available around Highwood. The network offers a good variety, with 18 routes considered easy and 16 routes rated as moderate, ensuring options for different skill levels.
Yes, Highwood offers several family-friendly road cycling options, particularly due to its generally flat terrain and extensive network of paved trails. Many routes pass through parks and forest preserves, providing a safe and enjoyable experience for families. An easy option is the Northcroft Park – Skokie Valley Bikeway loop from Highland Park.
While cycling in Highwood, you can explore significant natural features like the MacArthur Woods Forest Preserve, which showcases the original landscape of the Des Plaines River Valley. You might also encounter scenic lakes such as Skokie Lagoon No. 3 and Half Day Forest Preserve Ponds, which are popular for birdwatching. The North Branch Trail and the Des Plaines River Trail also offer picturesque views.
The best time for road cycling in Highwood is typically during the spring, summer, and fall months when the weather is mild and the trails are clear. The preserved forests and river valleys offer beautiful scenery during these seasons. While some trails may be accessible in winter, conditions can vary, so checking local trail conditions is advisable.
While Highwood's terrain is generally flat, some routes offer longer distances or slightly more varied landscapes that can provide a moderate challenge. For instance, the Fort Sheridan Pond – Skokie Valley Bikeway loop from Ravinia is a moderate 27.3-mile route that takes about 2 hours to complete, offering a good workout through varied suburban and natural settings.
Highwood and its surrounding forest preserves offer numerous access points with parking facilities. Many forest preserves and parks along the major trail systems, such as the Des Plaines River Trail and North Branch Trail, provide designated parking areas for visitors. It's recommended to check specific park or preserve websites for detailed parking information.
Yes, many road cycling routes in Highwood are designed as loops, allowing you to start and end at the same point. Examples include the Founders Park – Shelton Park loop from Highland Park and the Fort Sheridan Cemetery – Robert McClory path loop from Highwood, which offer convenient circular rides through local areas and along dedicated paths.
The road cycling routes in Highwood are highly regarded by the komoot community, with an average score of 4.9 stars from over 20 reviews. Cyclists often praise the well-maintained paths, the scenic passages through forest preserves, and the accessibility of the trails for various skill levels.
Yes, Highwood is part of a region with over 350 miles of managed trails. While individual routes might vary in length, you can combine sections of trails like the North Branch Trail or the Des Plaines River Trail to create longer distance rides. For example, the Founders Park – Shelton Park loop from Ravinia is a moderate 31.9-kilometer route that can be extended by connecting to other nearby trails.
Highwood is well-connected within the Chicago metropolitan area. While direct access to every trail might vary, public transport options like Metra commuter rail lines can bring you to towns near trailheads, from where you can cycle to the starting points. Checking local transit schedules and routes in advance is recommended.


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