We'll keep it short and sweet this week, Fellow Travelers! All you have to do is get yourself and your bike to the trail, and ride. Because, given the whims of Chicago weather, there's no time to lose. ​

Today I thought we'd take a little break from the regularly scheduled format, and dive into this glo-riooo-us fall weather with some nice long bike rides.

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.

So here, for your riding pleasure, are our hands-down favorite long bike rides near and around Chicago, plus several loop trails of 10 miles or more, all located within a 1-3 hour drive from the city. Some are entirely doable as day trip outings, others are probably better done as weekend or overnight trips.

These there are not training rides for competitive events, but recreational, breathe-deep rides, the kind that make you go AH!

The plan is very simple: get yourself to the trail by any means necessary, and enjoy all the glory that these midwestern fall days have to offer.

Here we go:

KalHaven Trail, MI

Spanning 34 miles between Michigan towns of South Haven and Kalamazoo, the KalHaven trail figures prominently as a top tourist destination in 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, passing 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.

Oak Leaf Trail, WI

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.

Our northern neighbor is a fabulous biking town with many natural and culinary attractions (and of course --beer🍺). More info at The Oak Leaf Trail page, trail connections at Milwaukee County Bike Map, and our own Milwaukee Meander.

Hank Aaron Trail, WI

If you’re not quite up for the magnitude of the above trail, and into more of an 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.

(If you end up spending a little more time in Milwaukee, here are some suggestions for quick forays into nature in and around town.)

Great River Trail, IL

​Great River 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.

Though the first few miles of the trail are marked by the profound lack of scenery, the level grade and smooth pavement allow for quick progress. Past the town of Albany, the trail curves past the historic 2000 years old Albany Indian Mounds.

After the half-way point, the trail was much more varied, with the final 7-mile section before Thomson being the most scenic of the whole trip, passing through shady woodland and beautiful expanse of prairie. A stately pine forest marks the entrance to Thomson Causeway.

At this point, I recommend riding down to the River Birch Campground 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.

NW Indiana Trail Network

This region is teeming with recreational bike trails, which span the three counties bordering Lake Michigan, and can be linked together into longer trips (or used as routes for the Lake Circle Tour).

Heading east out of Illinois, you can connect to Erie Lackanawa Trail. Just past the town of Griffith, this connects to the 10-mile Oak Savannah trail, which merges into the Prairie Duneland Trail in Hobart, for the remaining 10 miles into Chesterton.

From there, you can take the short Dunes Kankakee Trail to the Calumet Trail. You can pause here, and hike one of the most gogreous local trails at Cowles Bog. Or, keep heading east to the new Singing Sands trail into Michigan City.

Though Calumet Trail has been notorious for its poorly maintained gravel surface and enormous puddles, it is currently undergoing a transformation and re-paving over all of its length, as part of the future Marquette Greenway bike route from Chicago to New Buffalo, MI. Many online descriptions of this trail are inaccurate, and do not reflect these recent improvements.

Fox River and Prairie Path Microtour, IL

You can have a completely car-free, self-supported 60-mile day tour combining Metra, Prairie Trail, Fox River Trail, Prairie Path, and CTA Blue line to make a complete circle beginning and ending at Jefferson Park, without retracing your steps.

You could take the morning Metra train from Jefferson Park to Pingree Road, and complete the trip in one day, or turn it into an overnight, as we did, to make it a bit more vacation-like.

​Brompton folding bikes make for especially easy integration with trains, but any bike will work as long as you avoid rush hour train restrictions.

Ozaukee Interurban Trail, WI

​Ozaukee Trail, which starts a few miles north of Milwaukee, is about 30 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.

On approach to Belgium, WI at its northern end, there are spectacular birdwatching opportunities, with a good chance of spotting sandhill cranes this season as they ready for their fall migration.

If your time permits, in Belgium you have a couple of options to extent your trip:

Hop on some very low-key country roads to take a mid-ride break on the shores of Lake Michigan at Harrington Beach SP.

Segue seamlessly onto the Sheboygan Interurban Trail for another 14-mile ride which will take you within spitting distance of another lakefront State Park at Kohler-Andrae.

Hennepin Trail, IL

This is a 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.

Ogle County, IL.

Wow. If you have not visited Ogle County, I highly recommend it. It’s an easy getaway 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.

Old Plank Road & Hickory Creek Trails, IL

​OPR Trail is a linear 22-mile rail-to-trail between Chicago Heights and Joliet. It leads through oak groves and sugar maples, prairie grasses, and wildflowers, with many opportunities to view wildlife (including bald eagles!) while passing through nature preserves adjacent to the trail. One highlight is an award-winning, arrowhead-shaped suspension bridge, which takes trail users over US 45.

Heading west, a short distance past Wolf Road, don't miss the turn-off for Hickory Creek Bikeway --a little gem of a trail, which should be especially gorgeous amid fall leaf splendor. This rolling, hilly stretch of trail is not to be missed, and --though there are some climbs-- it is generally down(ish)-hill when heading west. If you want to avoid the more strenuous return trip, you can connect back to Old Plank via (the decidedly unscenic, but much flatter) Route 30 Bike Path.

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.

1. Tinley Creek Trail: about 10.5 miles of paved trails in a sequence of loops (map)
2. Busse Woods: about 11 miles of paved trails, plus elk viewing! (map)
3. ​Waterfall Glen: over 9 miles of rolling, crushed limestone trails with ravine views and waterfall.
4. ​Moraine Hills SP: 11 miles of lightly hilly, crushed limestone trails on three clover-leaf loops. Views of Lake Defiance and McHenry Dam (more info).
5. ​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.
6. Poplar Creek Trail at Arthur Janura Nature Preserve: several miles of paved and unpaved trails centered around a main paved 9-mile loop (map).

Alright. I hope that this provides a great launchpad for you two (or three!) wheeled Fall explorations. Happy trails, and let me know how it goes.

​ See you next week for another dose of --Justyna