Best Long Bike Rides Near Chicago

by Justyna Frank
long bike rides near Chicago

There’s always the North Branch Trail or the Lakefront, and sometimes the Des Plaines River Trail (when not flooded). But maybe you’ve ridden those, and you want something else.

Here are some of our best suggestions for best long bike rides near Chicago, plus several loop trails of 10 miles or more located within a 1-3 hour drive from the city. I should point out that these there are recreational and adventure rides, rather than training rides for competitive events. Some of these are entirely doable as day trip outings, others are probably better done as weekend or overnight trips. We’ve ridden on most of these trails, but not all. In time, we hope to have separate blog entries dedicated to each one, but there’s no reason you need to wait around for that before you go exploring. Here are some basic maps and resources to get you started.

Covered bridge on the KalHaven Trail
Stopping along the Fox River Trail
Harrington Beach State Park
  1. KalHaven Trail. Spanning 34 miles between Michigan towns of South Haven and Kalamazoo, the KalHaven trail figures prominently as a top tourist destination to the Southwest Michigan region. You can ride this hard-pack, mostly unpaved linear rail-trail in either direction for a spectacular 70-mile day-long excursion. You’ll pass through towns, woodlands and farmland. If you begin and end in South Haven, you’ll have the gorgeous Michigan Lakefront to enjoy, or if you choose Kalamazoo, you’ll have —beer. A solid bet either way. More info at Friends of the KalHaven Trail and Michigan DNR.
  2. Oak Leaf Trail. This is a monster 125 mile trail system around Milwaukee, consisting of several sections that can be strung into shorter routes, especially given the numerous intersections with other Milwaukee-area bike trails. This is a fabulous biking town with many natural and culinary attractions, and we’d be remiss if we did not mention the quintessential summertime Milwaukee tradition —beer gardens— a number of which are easily accessible from various points on the trail. More info at The Oak Leaf Trail page, trail connections at Milwaukee County Bike Map, and our own Milwaukee Meander ride account.
  3. Hank Aaron Trail. If you’re not quite up for the magnitude of the above trail, and are up for a more urban day exploration, the Hank Aaron Trail is an awesome way to see many of Milwaukee’s best attractions from the seat of your bike. If you start and end at the lakefront park (unlike in Chicago, parking is easy and not price-prohibitive), the round trip will be about 28 miles, passing near the Milwaukee Art Museum, Harley Davidson Museum, Urban Ecology Center, Mitchell Park Domes, and more.
  4. Great River Trail. This trail follows the Illinois side of the Mississippi River for 62 miles between the towns of Rapids City and Savana. We’ve ridden all of it in various sections, and we most heartily recommend starting toward the southern end in Port Byron, and riding to Thomson, where you can camp for the night if you wish to turn your trip into an overnight outing. Even if you don’t camp there, we recommend riding down to the River Birch Campground (see the last entry in this post) for a mid-ride bring-along picnic, and truly incomparable views of the widest point of the Mississippi, with glimpses of wading birds, pelicans and bald eagles.
  5. Three Floyds Ride. So, …um, we didn’t really mean for this to be a beer-themed post, but here we are. We know there are a lot of folks who ride from Downtown to Three Floyds, but that is quite a long ride, especially if you enjoy some of their liquid refreshments midday. For a still ambitious, but shorter (40-mile) alternative, we recommend starting in south suburban Chicago Heights and riding the beautiful Thorn Creek Trail into Indiana. Since we did this trip the first time, we’ve done our best to avoid the nightmarish Glenwood Lansing Rd, opting instead for a network of neighborhood streets directly north of it to cover the last couple of miles between the end of the trail and the brewery.
  6. Fox River-Prairie Path Loop (combine with trains). If you’re interested in doing a car-free, self-supported day tour, we love this combination of Metra, Prairie Trail, Fox River Trail, Prairie Path, and CTA Blue line to make a complete circle beginning and ending at Jefferson Park. Brompton folding bikes made for especially easy integration with trains, but any bike will work as long as you avoid rush hour train restrictions. Total riding distance was about 60 miles.
  7. Harrington Beach SP (combine with train). For another awesome overnight, this one involving camping, you can use almost entirely off-street bike trails to travel from the Amtrak station in Milwaukee to Harrington Beach SP. The trip is about 45 miles one way, and will take you through the beautiful towns of Cedarburg, Grafton and Port Washington, where there are plenty of opportunities for rest and refreshment. While the camping at Harrington Beach is not directly adjacent to Lake Michigan, if you have a bike, you can easily pop down to the park beach to cool off after your ride.
  8. Hennepin Trail. This is another vast trail system for multi-day explorations, located in western part of Illinois, about 2 hours from Chicago (depending on where you choose to begin). The three prongs of the trail radiate like spokes of a wheel in three directions, making it tricky to turn the whole thing into a continuous ride, but offering great options for exploration by section. The trail follows an old towpath, and is mostly unpaved, with plenty of places for camping and picnicking along the way. More info at Illinois DNR Hennepin Trail page, and interactive map here.
  9. Ogle County, IL. Wow. If you have not visited Ogle County, I highly recommend it. It’s very easy to get to from Chicago for some nice riding away from the crowds. Situated southwest of Rockford, IL, the county straddles both sides of Rock River, and includes Castle Rock SP and Lowden-Miller State Forest. Best of all, the county takes biking very seriously, providing on its website detailed maps of over 90-miles of scenic bike routes through the county. These are not bike trails, but well-vetted routes using quiet paved and unpaved rural roads with rolling terrain, beautiful scenery, and opportunities to see bison.
  10. BONUS: Super loops. Maybe you’re tired of linear trails, and you’d like to ride a distance without retracing your steps? Most of the loops below will give you at least 10 miles of riding.
    • Tinley Creek Trail: about 10.5 miles of paved trails in a sequence of loops (map)
    • Busse Woods: about 11 miles of paved trails, plus elk viewing! (map)
    • Waterfall Glen: over 9 miles of rolling, crushed limestone trails with ravine views and waterfall (info).
    • Moraine Hills SP: 11 miles of lightly hilly, crushed limestone trails on three clover-leaf loops. Views of Lake Defiance and McHenry Dam (info).
    • Rock Run Greenway Trail: At its northern end, this trail connects with the Joliet Junction Trail; at its southern end, with the Illinois & Michigan Canal State Trail. Together these three trails form a popular 16-mile loop.
    • Poplar Creek Trail at Arthur Janura Nature Preserve: several miles of paved and unpaved trails centered around a main paved 9-mile loop (map).

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