4.8
(59)
196
riders
26
rides
Touring cycling around Highwood features a landscape characterized by a network of dedicated bikeways and trails, connecting various lake areas and river paths. The region offers generally flat to gently rolling terrain, making it suitable for a range of cycling abilities. Key features include established routes like the Green Bay Trail and Skokie Valley Bikeway, which provide accessible paths through natural and developed areas. The elevation gains on routes are typically modest, with most ascents under 200 meters.
Last updated: July 2, 2026
5.0
(2)
30
riders
66.0km
03:59
170m
170m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(9)
21
riders
43.2km
02:31
130m
130m
The Small Lake – Skokie Valley Bikeway loop from Fort Sheridan offers a diverse touring cycling experience, blending long stretches of smooth, flat asphalt with more natural, picturesque sections. You'll…

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4.8
(10)
16
riders
42.1km
02:34
90m
90m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
17
riders
29.4km
01:56
50m
50m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
10
riders
33.0km
01:59
140m
140m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Highwood
Bahá’í House of Worship in Wilmette This is one of eight continental Bahá’í temples worldwide and serves as a spiritual center for all of North America. • The temple is open to people of all faiths and is intended as a place for prayer, meditation, and reflection, without sermons or organized worship services. • Inside, sacred texts from various world religions are read or sung without instrumental accompaniment. A domed prayer hall with nine entrances, nine alcoves, and nine fountains—the number nine symbolizing unity and spiritual wholeness. • Detailed concrete cladding in a lacy style, made of Portland cement and quartz. • Religious symbols from various faiths, such as the Christian cross, the Star of David, and the Islamic crescent, are incorporated into the exterior pillars. • Inside the dome, the “Greatest Name” is inscribed in Arabic script, meaning “O Thou Glory of Glories.”
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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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Interesting temple - very different from anything else on the North Shore.
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This easy multi-use trail makes its way through a number of neighborhoods and parks. It's a great place to escape to for a relaxing ride.
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This is a wonderful beach at Wilmette. You can spot migratory birds as they fly over Lake Michigan. It's a very diverse area for nature – sandy shore, dunes, parkland and native plantings. There's also a beach house and dog beach.
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From this location you'll have an amazing view across Lake Michigan to the Chicago Skyline in the distance.
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Set on the shores of Lake Michigan this is the second Baha'i Temple ever built. The Baha'i Faith is based in unity of all people therefore everyone is welcome to visit the temple.
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Lovely water feature behind / south of the Lighthouse
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Touring cycling in Highwood features a landscape characterized by generally flat to gently rolling terrain. The region boasts a network of dedicated bikeways and trails, connecting various lake areas and river paths. Most routes have modest elevation gains, typically under 200 meters, making them accessible for a range of cycling abilities.
There are over 20 touring cycling routes available around Highwood on komoot, offering a diverse range of options. These include 12 easy routes, 8 moderate routes, and 3 more challenging paths, ensuring there's something for every skill level.
Yes, Highwood offers several easy touring cycling routes suitable for families. These paths often follow dedicated bikeways through natural and developed areas, providing a safe and enjoyable experience. Look for routes with lower difficulty ratings for the most family-friendly options.
For experienced touring cyclists seeking a challenge, Highwood offers a few more difficult routes. One such option is the Independence Grove Lake – Des Plaines River Trail loop from Fort Sheridan, which covers 64.2 miles (103.3 km) with an elevation gain of around 196 meters, providing a longer and more demanding ride.
Highwood's touring routes often pass by beautiful natural and historical points of interest. You might encounter serene spots like Skokie Lagoon No. 3, the tranquil Half Day Forest Preserve Ponds, or the expansive MacArthur Woods Forest Preserve. Many routes also follow established paths like the North Branch Trail, offering diverse scenery.
Yes, many of the touring cycling routes in Highwood are designed as loops, allowing you to start and end at the same point. Examples include the popular Grosse Point Lighthouse – Green Bay Trail loop from Lake Forest and the Small Lake – Skokie Valley Bikeway loop from Fort Sheridan.
The touring cycling routes in Highwood are highly rated by the komoot community, with an average score of 4.98 stars from over 30 reviews. Cyclists frequently praise the extensive bikeways, the connection to various lake areas and river trails, and the overall accessibility of the routes for different skill levels.
The best time for touring cycling in Highwood is generally during the spring, summer, and fall months. Spring offers pleasant temperatures and blooming scenery, while summer provides warm weather perfect for longer rides. Autumn is particularly scenic with vibrant fall foliage, though cooler temperatures may require extra layers.
Absolutely. The region's network of bikeways is known for connecting various lake areas. For instance, the Skokie Lagoons – North Branch Trail loop from Fort Sheridan is a great option that takes you through the beautiful Skokie Lagoons area.
The touring cycling routes in Highwood vary in length to suit different preferences. You can find routes ranging from shorter, more leisurely rides to longer excursions. For example, the Skokie Valley Bikeway – Green Bay Trail loop from Lake Forest is about 26.1 miles (42.1 km), while other routes can extend up to 41.1 miles (66.2 km).
Yes, Highwood's touring cycling network prominently features established routes like the Green Bay Trail and the Skokie Valley Bikeway. These dedicated paths form the backbone of many popular loops and provide accessible cycling through the region.


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