From urban jaunts to small-town rides, each of these cities holds unique experiences that can only be enjoyed on two wheels.
Lakefront Bike Trail in Chicago
Credit: Abel Arciniega/Choose Chicago

When you're on a bike, you're seeing places from a completely different perspective than on foot or in a car. Local trails in the Midwest let you explore new places in new ways, with the freedom to pull off to grab an ice cream cone, pause at a lake or discover a nearby nature center. When you're ready to roll, check out eight of the best Midwest cycling destinations.


For a true urban biking experience, you'd be hard-pressed to do better than the city of Chicago. It has 200 miles of on-street protected paths plus options for off-street byways, like the 18-mile Lakefront Trail, with Lake Michigan vistas on one side and striking skyline views on the other. Immerse yourself in the city's bike culture at local bike shops (Kozy's, Comrade Cycles or the nation's largest bike store, the Village Cycle Center), or sign up for the popular, non-competitive 30-mile Bike the Drive event.


Minneapolis consistently makes lists of the best biking cities in America, and for good reason. With 98 miles of bike lanes and 101 miles of off-street trails and other bikeways, the city teems with bicyclists. If you're after waterside views, the 15-mile Chain of Lakes trail will deliver, winding alongside five local lakes. If you'd prefer a city feel to your ride, the 5.5-mile Midtown Greenway weaves by shops and restaurants.

Two cyclists biking on Madison, Wisconsin trail
Credit: Focal Flame Photography/ Destination Madison

Madison, Wisconsin

In Madison, you'll find over 200 miles of biking and hiking trails and dedicated bike lanes on city streets. One favorite path is the 13-mile Lake Monona Loop which encircles the lake and provides sparkling city views. Olbrich Botanical Gardens and Frank Lloyd Wright's Monona Terrace are well worth a rest stop along this path. You can also cruise UW-Madison's campus en route to Picnic Point, the best spot in town to see sunsets. Need to rent some wheels? Check out BCycle electric bikes or Machinery Row Bicycles.

Hamilton County, Indiana

If you want to get off the beaten path, plan a cycling trip to Hamilton County, located just outside Indianapolis. You'll find 500 miles of trails with options for all abilities. Mountain bike enthusiasts can head to Flat Fork Creek Park for a progressive course that caters to beginners, and everyday cyclists can pedal the 25-mile Monon Trail, a former railroad corridor that flanks peaceful sites like the Kawachinagano Japanese Garden.

Xenia, Ohio

This quiet Ohio hamlet of 26,000 has been nicknamed the Bicycle Capital of the Midwest. While Xenia's in-city paths only come out to 14 miles, the town serves as a hub for 519 miles of trails that span the state. Pack a picnic to enjoy at Xenia Station, a former railroad depot with picnic tables, play equipment and nature areas before setting out on the 78-mile Little Miami Scenic Trail or the 30-mile Prairie Grass Trail.

Two adult women biking the High Trestle Trail Bridge in Iowa outside of Des Moines

Des Moines

Des Moines holds a treasure trove of bike paths for recreational and avid cyclists alike, especially those training for the Register's Annual Great Bicycle Ride Across Iowa (RAGBRAI). In the metro area, trails meander through green spaces like Gray's Lake and Water Works Park, with myriad opportunities to refuel and rehydrate along the way (El Bait Shop and Confluence Brewing are two local faves). If you want to ride a real-deal railroad trestle from back in the day, bike the 25-mile High Trestle Trail that overlooks the Des Moines River. Or try the scenic 26-mile Chichaqua Valley Trail, which connects Berwick to Baxter. Not able to travel with your bike in tow? You're covered with the BCycle program and nearby shops like Bike World.

Kalamazoo, Michigan

You may know Kalamazoo best as HQ for Bells Brewery, but it also lies along one of Michigan's Great Lake-to-Lake trails. Route #1 spans 275 miles, linking 34 communities from Lake Michigan to Lake Huron. The city itself is home to a variety of paved, gravel and dirt trails; you can even create your own route to see some of Kalamazoo's public art works. There's no shortage of bike-related events here either. Come to Kalamazoo Bike Week for group rides and informative classes.

Rapid City, South Dakota

Only a few miles from the eastern edge of the Black Hills National Forest, Rapid City is a cyclist's paradise—in fact, it may soon become an official Bicycle Friendly Community. The city features 137 miles of trails and many guide riders to iconic destinations. One notable route runs from Rapid City to Mount Rushmore. Or for a glimpse of the Black Hills, pedal Custer State Park Spur, a moderate 3.2-mile paved path.