Best Bike Rides Chicago  by Ted Villaire

Best Bike Rides Chicago Guide Book

by Ted Villaire (Falcon Guides)
Best Bike Rides Chicago  by Ted Villaire
Written for cyclists of all stripes, Best Bike Rides Chicago presents a diverse array of scenic tours in and around one of America’s prime urban destinations—from easy excursions for the Sunday cyclist to challenging treks for the veteran. Author and cyclist Ted Villaire describes thirty-four rides in and around the Windy City. This guide indeed has plenty to choose from. Chicago and its environs offer gentle terrain, the lakeshore, an abundance of bike paths, and unique neighborhoods and communities to explore. Farther out—whether you’re in the collar counties, Indiana, Michigan, or Wisconsin—you’ll find scores of parks with rivers, lakes, woodlands, wetlands, and restored prairie . . . not to mention quiet farm roads, charming towns, and unforgettable restaurants and shops.

© 2011 Ted Villaire/Falcon Guides. All Rights Reserved.

Trails from the "Best Bike Rides Chicago" Guide Book
Displaying trails 20 of 34.

Displaying trails 1 to 20 of 34.

Given the bustle of the surrounding suburban landscape, the rural character of this ride seems unlikely. As you encounter the oak-covered hills, sprawling marshlands, and farms mixed in with a scattering of often-palatial houses, you’ll find yourself congratulating the local residents who fought to preserve the area’s rural charm. When Chicago businessmen and their families began coming to Barrington after World War I, they were attracted to the rural setting and saw the potential to create a genteel atmosphere in the Chicago suburbs. They transformed old farms into estates and established numerous horse farms and riding facilities.
Chicago, IL - Road Biking - Trail Length: 28.9
This ride opens with a short stint on a heavily wooded section of the Major Taylor Trail, one of the newest trails in Chicago. The route in Beverly takes you by a collection of historic mansions, including one that was modeled after an Irish castle. From Beverly, you’ll head west through the quiet streets of Mount Greenwood and pass some of the local cemeteries for which the area is known. After tours of the suburban towns of Oak Lawn and Evergreen Park, you’ll return to Beverly to gawk at more of the sprawling mansions.
Chicago, IL - Road Biking - Trail Length: 17.9
This ride takes you through a scenic setting that straddles the Illinois-Indiana state line just 40 miles south of downtown Chicago. The landscape features gently undulating farmland broken up regularly by swaths of woodland, occasional small hills and ravines, and streams that braid the landscape. At the ride’s halfway point, you’ll explore the Indiana community of Cedar Lake, a former resort town on the shore of a gleaming natural lake.
Chicago, IL - Road Biking - Trail Length: 44.7
Enjoy a classic Chicago bike ride along the Lakefront Path as it winds past harbors, beaches, the dazzling skyline, and the big blue mysterious lake. After passing the museum campus and Soldier Field, you’ll leave the well-beaten biking path and head into the neighborhoods of Pilsen and Little Village and then meet up with the Chicago boulevard system. The boulevards guide you through three large Chicago parks sprinkled with gardens, lagoons, and elegant park buildings. The final section of the route tours several of Chicago’s North Side neighborhoods.
Chicago, IL - Road Biking - Trail Length: 29.6
This ride reveals a part of Chicago that is vast and persistently interesting. Visit four great Chicago South Side parks, follow the Lake Michigan coastline, and explore Pullman, a nineteenth-century planned neighborhood of Victorian row houses. The route also takes you through areas of heavy industry for which the South Side is known. While exploring the wetlands of the Lake Calumet area, it’s hard to believe that you’re still in the city of Chicago.
Chicago, IL - Road Biking - Trail Length: 27.7
If you like riparian landscapes, you’ll love the Des Plaines River Trail as it winds alongside tree-laden riverbanks, through dense bottomland woods, alongside ponds, and over footbridges. Quiet oak savannas and many acres of tall grass prairie thick with goldenrod, asters, and big bluestem prairie grass decorate the trail borders. Spanning nearly the entire length of Lake County, the trail gives visitors an extended encounter with this attractive river and the surrounding— mostly wet—landscape.
Chicago, IL - Cross-Country Skiing,Horseback Riding,Mountain Biking,Rail-Trails,Road Biking,Trail Running - Trail Length: 49.6
Located only 30 miles west of downtown Chicago, the Fox River Trail has plenty of great things going for it. As this pathway hugs the Fox River between Aurora and Algonquin, it passes numerous community parks and forest preserves. In Elgin the Fox River Trolley Museum sits alongside the trail. In Geneva the 300-acre Fabyan Forest Preserve contains a restored Dutch windmill. Also alongside the trail at Fabyan are a pristine Japanese garden and the Villa Museum, designed by Frank Lloyd Wright. Some of the towns the trail passes through—such as Elgin, Geneva, and Batavia—contain attractive urban riverfront areas with flower and sculpture gardens, pedestrian bridges, and scenic walkways.
Chicago, IL - Cross-Country Skiing,Rail-Trails,Road Biking,Trail Running,Walking - Trail Length: 65.6
As the Great Western Trail makes a straight shot west from Villa Park, it cuts through residential areas and brushes against community parks and forest preserves. On the second half of the route, woods, prairie, and wetlands become more abundant as houses and trail users grow sparse. Consider short side trips to Churchill Woods Forest Preserve at the halfway point and Kline Creek Farm near the end of the trail.
Chicago, IL - Road Biking - Trail Length: 11.7
Setting out toward Sycamore from St. Charles, the first half of the path presents you with attractive woodland intermingled with acres of bright and shiny housing developments. A rural landscape takes over on the second half of the path as it slices through wide-open agricultural land alongside IL 64.
Chicago, IL - Road Biking - Trail Length: 34.2
In 1848 the Illinois and Michigan Canal provided the final shipping link between the East Coast of the United States and the Gulf of Mexico. From Chicago the canal angled southwest, running beside the Des Plaines and Illinois Rivers halfway across the state. Thanks to the 96-mile-long canal, Chicago quickly became the largest and most efficient grain market in the world. The canal towpath, originally used by mules for pulling boats through the canal, has been transformed into a 61.9-mile crushed gravel path running from the outskirts of Joliet to the town of La Salle. From end to end, the route wanders through a variety of landscapes: dense woods, marshes, prairies, riverbank, agricultural land, and small towns. The length of this trail may present a challenge even for well-prepared athletes. While amenities exist along the way, some sections are very remote. The trail crosses a handful of busy roads. Use caution while crossing these. Small sections of the trail are occasionally closed due to erosion.
Chicago, IL - Backpacking,Cross-Country Skiing,Horseback Riding,Mountain Biking,Rail-Trails,Road Biking,Trail Running,Walking - Trail Length: 61.9
This route is jammed with scenic vistas and fascinating local history. While tracing the route of the Des Plaines River, the Chicago Sanitary and Ship Canal, and the I&M Canal, you’ll pass two museums, several parks, and a couple of historic sites. Much of the northern half of the route offers a surprisingly remote feel as it cuts through many acres of wetlands and bottomland woods. The trail is paved for the first 9.2 miles in Cook County; the trail surface is crushed gravel for the remaining 10.9 miles in Will County. The terrain is flat throughout. Things to see include: Des Plaines River, Chicago Sanitary and Ship Canal, bottomland woods, prairie, Isle a la Cache Museum, the I&M Canal, the I&M Canal Museum and Visitor Center, and the Joliet Ironworks
Chicago, IL - Road Biking - Trail Length: 40.2
These two connected branches of the Illinois Prairie Path take you through a suburban landscape that is largely residential, sometimes industrial, and often feels more remote than it actually is. As the route cuts through a number of forest preserves, the dense trailside greenery falls away and majestic views of wetlands and prairie open up in front of you. At roughly the route’s halfway mark, budget some time for checking out the shops and restaurants in Wheaton.
Chicago, IL - Road Biking - Trail Length: 54.4
The Illinois Prairie Path, one of the first rail trails in the nation, runs along the route of the former Chicago, Aurora, and Elgin Railway, an electric railroad line that carried commuters and freight between Chicago and its western suburbs. Stretching from Wheaton to Maywood, the main stem of the Prairie Path takes you through wooded parks and greenways and offers a taste of a handful of communities that grew up alongside this route. Before heading east on the trail, consider taking the 1.5-mile trip west along the path into downtown Wheaton, where restaurants, bars, and shops line the streets. Along the way you’ll pass Wheaton College, which contains a museum focusing on the school’s most famous alumnus, the evangelist Billy Graham. The trail also passes a large Romanesque-style courthouse built in 1896 that is now on the National Register of Historic Places. The building, topped off by a large clock tower, was recently remodeled and now contains high-priced condos. The west side of Wheaton is where the Prairie Path splits into two main branches; one goes to Aurora, the other to Elgin.
Chicago, IL - Cross-Country Skiing,Horseback Riding,Mountain Biking,Rail-Trails,Road Biking,Trail Running,Walking - Trail Length: 26.8
The 3 miles of beachfront on this ride offer one of the most delightful stretches of bike-able lakeshore in the region, the sort of road that makes you want to pull off every half-mile just to gaze at the striking scenery. Along this stretch, you’ll come upon some curious houses transplanted in the 1930s from Chicago’s World’s Fair. Before arriving at the shoreline, the ride takes you through about 15 miles of quiet, gently rolling rural roads located south of the park.
Michigan City, IN - Road Biking - Trail Length: 22.4
As you circle the far western edge of Joliet on this ride, you’ll get an inkling of the city’s industrial heritage, as well as its residential life, its parks, and its commercial districts. The first half of the ride guides you through the wooded campus of Joliet Junior College and the Rock Run Greenway, which comprises several connected parks and forest preserves. The second half of the ride features a series of neighborhoods, a swath of heavy industry, and the I&M Canal Trail.
Chicago, IL - Road Biking - Trail Length: 15.9
While circling Geneva Lake, you’ll begin to understand why the captains of Chicago industry built their summer homes on the shoreline of this postcard-perfect lake in southeastern Wisconsin. The lake’s wooded bluffs, the quaint lakeside towns, and swanky resorts continue to draw people from Chicago and Milwaukee. Most of the action on this ride takes place on the northern shore of the lake as you pedal through towns, past beaches, and along the shore of Lake Como. This is also where you’ll come across the glorious Yerkes Observatory.
Chicago, IL - Road Biking - Trail Length: 20.2
Enjoy plenty of ups and downs along this route as you follow a series of nearly perfect cycling roads outside of LaPorte, Indiana. Take a break from the rolling—sometimes hilly—terrain as you follow the shoreline of a couple of lakes north of town. At Stone Lake, you may want to take a dip in the lake and then unpack the pannier for a picnic. Sometimes called “The City of Lakes,” LaPorte, Indiana, is unusual for the many natural bodies of water clustered tightly together on the north side of the town. In addition to the scenic lakes and plenty of local parkland, LaPorte hosts a collection of large Victorian homes, an extensive local history museum, and a well-appointed courthouse in the center of town. Sound idyllic? Well, not always. On the north edge of LaPorte, you’ll pass near a place where morbid events interrupted life in this peaceful town during the early years of the twentieth century.
La Porte, IN - Road Biking - Trail Length: 32.3
As you travel from one side of Boone County to the other on the Long Prairie Trail, you’ll encounter small winding creeks, a few small railroad towns, and plenty of open space. Leaving Boone County launches you on the Stone Bridge Trail, where the greenery grows thick and the landscape becomes more rolling. Toward the end of the route, a short trip off-trail brings you to a picturesque landmark—an old double-arched limestone bridge straddling a rocky creek.
Chicago, IL - Road Biking - Trail Length: 40.8
When the last glacier receded from the landscape at Moraine Hills State Park nearly 16,000 years ago, it left behind a mosaic of marshes, prairies, bogs, hills, and streams, as well as the park’s centerpiece, Lake Defiance. The landscape surrounding Lake Defiance is peppered with a series of moraines—mounds of dirt and gravel. While these glacially sculpted hills aren’t huge by any measure, they offer a welcome retreat for nearby Chicagoans.
Chicago, IL - Road Biking - Trail Length: 9.5
The first part of this ride follows the North Branch Trail, one of the great bike pathways of Chicagoland, as it meanders along the wooded banks of the Chicago River’s North Branch, through the Skokie Lagoons, and ending at the Chicago Botanic Garden. The route’s second part follows the Green Bay Trail through the tony North Shore towns of Glencoe, Winnetka, Kenilworth, and Wilmette. The route’s final leg runs through a small arboretum in Evanston, a 2-mile-long outdoor sculpture park in Skokie, and a handful of Chicago residential neighborhoods.
Chicago, IL - Road Biking - Trail Length: 32.7