An Illustrated Guide to Chicago’s Best Long Bike Rides

Three great weekend routes — beer stops and photo ops included

June 22, 2017 9:00 am

Ah, the Midwest, where you can experience mile after uninterrupted mile of flatlands.

A scenic drive, they do not make.

But they’re a big-time plus when it comes to knocking out a 30-mile bike ride, which happens to be an excellent way to spend a summer weekend morning.

We recently asked three in-the-know Chicagoans to disclose their absolute favorite rides. Then we mapped ‘em all out, with plenty of stops and photo ops along the way.

Also: beer. It’s important to stay hydrated out there.

Matt Duer, Assistant Manager at Rapha Chicago

The route: The North Shore loop, from Wicker Park to Fort Sheridan and back. “We work our way out of the city north on the Lakefront Trail before 7 a.m. — the earlier the better, as it gets congested later in the day,” Duer says. Keep heading north toward Evanston, hopping on Sheridan Road when Lake Shore Drive ends. Follow Sheridan as it winds through the North Shore ‘burbs and flip at Fort Sheridan.

The mileage: About 60 miles
The sights: Lake Michigan, Northwestern University, the Bahá’í Temple and secluded tree-lined streets
The fuel: Duer grabs coffee at the Rapha Clubhouse before hopping on the bike. Then, on his way back to the city, he oftentimes makes a slight detour to refuel at Other Brother Coffeebar (1549 Sherman Ave., Evanston), a cyclist-owned cafe.
1514 N. Milwaukee Ave.

Alex Tweedie, Co-Owner of Roscoe Village Bikes

The route: The North Branch Trail. “It starts at Caldwell Woods and can take you all the way to the Chicago Botanic Garden through Skokie Lagoons,” Tweedie says. “There are so many places to stop and hang along the way, or you can just ride to the Botanic Garden, have lunch and turn around.” There are a few major roads between your start and finish, but overpasses set you up for miles with hardly any pauses.

The mileage: 30 miles
The sights: Woodsy forest preserves, lagoons and the picturesque Chicago Botanic Garden
The fuel: Tweedie suggests hitting the Garden View Cafe at your turnaround point. But don’t overdo it. You’ve got to get back on the bike to knock out another 15 miles.
2016 W. Roscoe St.

Gillian Fealy, Owner of Live Grit

The route: Southwest, starting from Live Grit HQ in the West Loop and heading out of the city along Ogden Avenue. “The ride winds through the southwest suburbs of Berwyn and Riverside before we hit the rolling hills of German Church Road,” Fealy says. Turn off Ogden onto Gilbert Avenue in Western Springs. That’ll turn into Willow Springs Road, which intersects with German Church Road about 5.5 miles south of Ogden.

The mileage: 44 miles
The sights: Lagunitas Brewing Company, Brookfield Zoo, stretches of city and suburbia, plus some incline for good measure
The fuel: Fealy’s group stops at a gas station to fuel up on water and snacks (ice cream isn’t off limits) before turning around and heading back to the city. Once back at the shop, cold beers are the reward.
1010 W. Monroe St.

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