Lakefront cycling is great and all—but why take that same route over and over? Bust out of your rut with these six alternatives. They were recommended to Chicago by the following passionate cyclists (listed in order of the routes on the opposite page): John Greenfield, editor of the transportation site Streetsblog Chicago; Brett Ratner, editor in chief of The Chainlink, a cycling website; Julie Deardorff, a certified personal trainer in Evanston; Mike Salvatore, owner of Heritage Bicycles in Lake View; Randy Warren, a cycling coach in Chicago; and Yasmeen Schuler, executive director at The Chainlink.
1. Tour de Tiki
Route: Downtown to River Grove
One-way trip: 13 miles
Details: Start at the acclaimed tiki bar Three Dots and a Dash (435 N. Clark St.). Then pedal south on Clark Street, west on Kinzie Street, northwest on Milwaukee Ave., and north on Kedzie Ave. until you hit the new Polynesian paradise of Lost Lake (3154 W. Diversey Ave.). Next stop: the tiki granddaddy Hala Kahiki in River Grove (2834 River Rd.). Huff west on Diversey, cut over to Grand Ave., and turn right on River Rd. Drink your fill: You’ll be taking a bike-friendly Metra train (the River Grove stop is nearby) back to the city.
2. Wilderness Revisited
Route: Schiller Woods to Des Plaines
Round trip: 16 miles
Details: At the Schiller Woods Forest Preserve near O’Hare, pedal north on the Des Plaines River Trail under a canopy of old-growth trees. Check out the wildlife (blue herons, beavers, foxes) and the river views. (Experienced off-roaders can veer onto offshoots that return to the main trail.) Once you hit Des Plaines, return the way you came. Boom: You’ve just enjoyed a 90-minute wilderness fix.
3. Garden Route
Route: Evanston to Glencoe
Round trip: 20 miles
Details: Even little kids can handle this ride on a tandem bike (it takes one hour each way). Go north on Poplar Ave., which becomes the wooded Green Bay Trail, winding through some pretty North Shore towns. Once you hit Lake Cook Rd., turn west onto the North Branch Trail addition. You’ll cruise directly into the stunning 385-acre Chicago Botanic Garden, where you can lock up your bikes to take a stroll through the greenery. Too tired to pedal back? Metra’s Braeside stop is a stone’s throw away.
4. Horsy Loop
Route: Barrington Hills
Round trip: 26 miles
Details: From the wonderfully divey Penny Road Pub (545 Penny Rd.), head north on Old Sutton Rd. and turn right on Otis Rd. You’ll pass a bucolic scene: rolling hills, horse pastures, and estates. Turn right on Dundee Rd. and left on Illinois Rte. 59, which takes you through downtown Barrington. You’ll eventually complete a big loop that takes you through the tall grass of the Spring Creek Forest Preserve. Return to the pub—this time for a burger.
5. Water Coming and Going
Route: Buckingham Fountain to Wolf Lake (bordering Indiana)
Round trip: 36 miles
Details: Take the lakefront path south, switching to South Shore Dr.’s bike lanes when the path ends. At 79th St., head southeast on U.S. Rte. 41’s bike lanes, which wind through the old U.S. Steel property and cross the Calumet River. Pick up the Burnham Greenway Trail, then enter the William W. Powers State Recreation Area: You’re a quick jog from the edge of Wolf Lake. Perhaps the best part: Your ride back offers killer skyline views.
6. A Little Bit of Everything
Route: Uptown to Lake Bluff
Round trip: 50 miles
Details: This daylong ride takes you from urban jungle to manicured suburbs to relaxed countryside. After navigating streets on the North Side and North Shore, take Forest Way north from Winnetka, passing the picturesque Skokie Lagoons. In Highwood, pick up the tree-lined Robert McClory Bike Path to charming Lake Bluff. Cool off with a beverage at Lake Bluff Brewery (16 E. Scranton Ave.) before you head home.