14 Great Midwest Bike Trails

To evoke the sensation of descending into one of Iowa’s historical coal mines, 41 steel frames spiral the ½-mile, 13-story bridge traversing Des Moines River Valley. It’s even more dramatic at night when blue LED lights on these “cribs” glow. Stop at one of the six observation decks on the bridge to see its supports—pillars from the original train treste—and read about wildlife. The 25-mile trail runs between Ankeny and Woodward. (515) 288-1846; inhf.org

You’ll find yourself winding through woodlands, wetlands, farms and fields on this route. Silos and farmhouses are blurs at the edge of the small town of Elroy, where the converted rail-trail begins (60 miles northwest of Madison). You can head out on a multiday adventure, choosing from more than 100 miles that vary in length and difficulty. Three old tunnels add chilly mystery to the easygoing ride. (608) 463-7109; elroy-sparta-trail.com

Ghosts of the railroad’s past dot this trail: bridges, weathered mileposts, a depot and the Neligh Mills gristmill. From Chadron to Norfolk in northern Nebraska, the 321 miles (only 195 miles are finished) will follow what was called the Cowboy Line past farmland, ranches and canyons. Get a bird’s-eye view of the Niobrara River from bridges soaring more than 145 feet. bikecowboytrail.com

Stunning scenery (and no hills) link Charlevoix, Petoskey and Harbor Springs as you cut through wooded residential areas and hug portions of Lake Michigan shoreline. The best views on the 26-mile trail are south of Petoskey, but you’ll also want to make your way north to explore the sand beaches of Petoskey State Park, where teens bake on towels and families play in the waves of Lake Michigan. (231) 823-0015; michigan.org

It’s named for the trout hatchery it passes and Trout Run Creek you skirt, but in addition to the sparkling waters, you’ll see sculptures and a 7-foot-long mosaic on this 11-mile loop in Decorah. At night, the bridge over State-9 glows with LED lights in colors to suit the seasons. (800) 463-4692; troutruntrail.com

The romance of small towns, orchards and even a covered bridge beckons from the 34-mile Kal-Haven Trail Bike Trail. Stretching from Kalamazoo to South Haven—thus its name—the former rail bed is now a fine gravel surface with some sections blacktopped. kalhavenbiketrail.com

Extending 18 miles from Hollywood Avenue on the north end of Chicago to 71st Street on the South Side, the trail leads cyclists through parks, beaches and gardens. Tourists appreciate that the trail links many of Chicago’s big-name attractions, including Buckingham Fountain and Soldier Field. (312) 744-3334; choosechicago.com

Named for its many curves and turns, the 26-mile trail takes in tidy farms, rustic wooden bridges and the bubbling creeks of Amish Country in Elkhart, Middlebury, Goshen and Shipshewana. pumpkinvine.org

This 240-mile, rails-to-trails bike route runs right through the heart of Missouri—its fields, forests, rivers and towns. Stretching from Clinton to Machens, the trail will eventually encompass 300 miles when it connects Kansas City to St. Louis. The crushed limestone path keeps your pace sedate, which means you’ll have plenty of time to enjoy the wildlife (muskrats, turtles, heron); wildflowers; canopies of maple, ash and oak; and the Missouri River. bikekatytrail.com

Contrary to its name, the 61-mile Illinois Prairie Path actually winds cyclists past more ponds, wetlands and forests than prairies. Leaping suburb to suburb out of Maywood (20 miles west of Chicago), riders eventually choose one of four crushed-limestone spurs to end up along the Fox River near Elgin, Geneva, Batavia or Aurora. (630) 752-0120; ipp.org

Just north of Indianapolis, the Monon Rail Trail stretches 7.6 miles from 96th Street to Fall Creek. Dozens of residential neighborhoods and parks line the route. Pack a picnic lunch or grab a bite at one of the restaurants along the trail. (317) 327-7431; visitindy.com

With peaks towering on all sides, the George S. Mickelson Trail snakes through South Dakota tunnels and across 100 trestles, where trains serving Black Hills gold mines once rumbled. The 109-mile route (named after the state's late governor) follows a century-old railbed from Deadwood south to Edgemont, treating bicyclists to the best of both worlds: mountaintop views and mostly easy pedaling. mickelsontrail.com

Pause near the steep drop-offs to drink in the view of the Little Missouri National Grasslands on this 144-mile path. The Maah Daah Hey Trail’s northern point is 15 miles south of Watford City (about 180 miles northwest of Bismarck). parkrec.nd.com

Starting west of the bridge in Milford and running right through the little town of Loveland (about 25 minutes northeast of Cincinnati), the former railbed has become a tranquil way to tour southwest Ohio. Soak in quaint towns, river views and pretty woodlands as this scenic path plays hide-and-seek with the Little Miami River. littlemiamibiketrail.com