Explore the best rated trails in Chicago, IL. Whether you're looking for an easy walking trail or a bike trail like the Illinois & Michigan Canal State Trail and ComEd Greenway. With more than 115 trails covering 4803 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
Gradual down hill slope (or uphill depending in which end you start on). Busy road but peaceful area. We added the dead end at the south end of the bike path for a total of 4 miles.
Centennial Trail in good shape with a few minor bumps. Mostly flat and worth the trip to get there. Rode it in June 2023 and enjoyed it!
Trail is in great condition, hardly any bumps and just a small hill climb east of the trout farm.
It can get congested on weekends/holidays.
Very scenic views with forested and open areas.
It is about a 5-mile round trip from Royce Road to Indian Boundary Park.
There is a 2 mile connecting loop from the trout farm that goes around Whalon Lake.
Is what my cycling companions noted about this trail when we rode it to its end and back. The scenery is varied, there isn’t that much traffic (no Lycra Brigades) and the surface is nice and smooth. Yes, there are two places where you will cross busy highways, but there are stoplights in both places. We parked in the Lake Forest train station parking lot and took the Robert McClory to the trailhead in Lake Bluff. Another bonus: there’s a Culver’s and a Dairy Queen-type place along the trail. It also connects to other bike trails.
Looked this up spontaneously and it was just a beautiful ride! Perfect date for my husband and I!
Perfect if you’re looking for a leisurely ride. Paved trails. Great for beginners. Several bridges to cross in the woods. You have to cross a few busy streets but nothing to bad. We did about a 10 mile loop on the red trail starting by Arrowhead Lake.
As a dentist with a penchant for thrilling outdoor escapades, I recently embarked on an adrenaline-fueled gravel expedition like no other: Calumet trail. Allow me to share my firsthand experience and rate this trail a solid 4 out of 5 stars.
From the moment I saddled up, it was evident that this ride would put my skills and endurance to the test. The gravel terrain presented a formidable challenge, demanding unwavering focus and precise control. The relentless rain turned the path into a treacherous, mud-covered rollercoaster, adding an extra layer of intensity to the journey.
Despite the daunting obstacles, I couldn't help but appreciate the breathtaking beauty that enveloped me. Towering trees and verdant landscapes created a stunning backdrop, reminding me of the untamed wonders of nature. Catching glimpses of wildlife along the way added an element of awe to the experience, showcasing the harmonious coexistence between humans and the natural world.
However, let me emphasize that this trail is not for the faint-hearted or inexperienced riders. The technical demands and physical exertion required are not to be underestimated. Prior preparation, both mentally and physically, is vital to fully embrace and conquer this challenging course. A reliable and robust bike, such as my trusted companion, the Sirvelo, is an absolute must for tackling the rugged terrain.
Amidst the hardships, a sense of triumph washed over me with each conquered section of the trail. The sheer satisfaction of pushing my limits and overcoming the obstacles was an extraordinary feeling, fueling my passion for adventurous pursuits.
In summary, Calumet trail is an adventure that beckons seasoned gravel enthusiasts to rise to the occasion. With its demanding terrain, awe-inspiring natural surroundings, and an invigorating rush of adrenaline, this trail earns a solid 4-star rating. So, fellow adventurers, don your gear, prepare for an unforgettable journey, and let this gravel odyssey ignite the thrill-seeker within you, even if you're a dentist like me!
Today, we rode from Dean Nature Sanctuary to the 7-11 just south of Busse Woods and back. About 34 miles, from the parking lot of the Sanctuary. Good option during the 294 construction that has the path closed at that location. Some parts of the Salt Creek path are very bumpy.
Rode from hammel woods (on black road) north to trailhead at sunset park in plainfield then south back through woods to trailhead at jefferson street in shorewood, about 10 miles roundtrip.
North of black road the asphalt pavement is flat and in excellent shape. Trail goes from the woods parking lot then north under black road and through a wide prairie along the river with no shade. South of black road the trail winds through the woods with very little slope and asphalt pavement is in good shape. Easy riding all the way.
watch out for construction in the southern end of the trail—passable right now, but it may not be in a few weeks.
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