Elston is quite possibly the only road in the country that starts and ends on the same street (Milwaukee Avenue), so to be able to say you traversed the whole damn thing, start at the Café Sandwicheria (455 N Milwaukee Ave) for a hearty fuel-up with a classic turkey, bacon and swiss sammich. Then pedal north, take a gentle right onto Elston, and head past factories and drawbridges to the Hideout (1354 W Wabansia Ave at 1700 N Elston Ave) for a frosty one (drinking and driving is dangerous on two wheels, too) with the hipsters. If you’d like “one for the road,” try the Wine Discount Center (1826½ N Elston Ave), just a little north. They hold a wine tasting every Saturday from noon–4pm, no charge. Pop a bottle in your panniers and head up to Urban Gardener (2211 N Elston Ave), a garden shop with botanical baubles at every turn—last time we were there, they had gorgeous bell jars perfect for violets or orchids. Now it’s on to the long last leg of your journey: The trek to hot-dog Valhalla, Superdawg (6363 N Milwaukee Ave), where the fries are delicious and the vibe is straight-up ’50s. If you’ve still got energy to burn, you’re right at the start of the North Branch trail, where 16 tree-lined miles will take you all the way to the Chicago Botanic Garden. Now that we think about it, you should probably eat two hot dogs at Superdawg.
Elston Path - Damen Path - MLK Path
The Damen bike lane provides lots to see, but remember the painted lines are not an invisible force field—keep an eye out for cars parking or pulling out. Start your trek at Open End Gallery (2000 W Fulton St), an arts and events space that will feature the folk-poppy band Fruit Bats on May 6 at 9pm. Peddle north and drop in to Sprout Home (745 N Damen Ave), a home-and-garden shop that offers everything from acacia-wood serving bowls to tomato plants. Another two blocks takes you to Just Baked (901 N Damen Ave), for delicious homemade sandwiches and ice creams. The menu changes seasonally, but the “Frenchie” ($9)—brie, green apple and cracked-pepper vinaigrette on a baguette—is a current favorite. Roll across the street to Willow (908 N Damen Ave), which offers nature-girly housewares and beautiful sterling-silver rings and necklaces by owner Amy Doehla. It also offers facials and waxing in the back, so if your eyebrows are out of whack, make some time for a tune-up. Another few blocks up brings Paper and Print (1940 N Damen Ave), with a staggering selection of papers, envelopes and hand-made wrapping papers to make posh gifts posher. Cap off your tour de Damen with some refreshing ceviche maki at BYOB sushi joint Coast (2045 N Damen Ave).
Dr. Martin Luther King Jr. Drive takes you through the heart of Bronzeville, along a scenic route of trees and massive graystones. Start at the Monument to the Great Northern Migration (King Dr and 25th St), a statue of a suitcase-toting man that commemorates African-Americans who came to Chicago in the 1920s. Follow the Bronzeville Walk of Fame (25th St to 47th St) past the Victory Monument to the Eighth Regiment (at 35th St), built in honor of an African-American fighting unit that served in World War I. Stop at the Jamaican Market Place (4655 S King Dr) to pick up some jerk spices for summer barbecues, or a Ting grapefruit soda. After your pit stop, head to comedy club Jokes & Notes (4641 S King Dr). It hosts established touring comics on Fridays and Saturdays, often folks with some BET appearances under their belts. If you’ve got time, stop in at Blu 47, a Cajun-inspired restaurant in the same shopping center, and snag some spicy conch fritters. Another five blocks or so, and you’ve reached Washington Park and the end of the official bike lane. If you’re not ready to call it a day, continue down the park to South Chicago Street and bear left, where a bike lane will take you to the breathtaking, historic Oak Woods Cemetery, final resting place of Chicago notables such as Mayor Harold Washington.