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The young woman behind the counter seemed a bit wary of two Caucasian strangers, as if she suspected we were undercover cops. Perhaps the place fills up after church services let out. The wall behind the counter was crowded with framed photos of regulars, memorabilia from the Civil Rights Movement and a Sears Tower-shaped plaque honoring the late Mayor Harold Washington.Īt 11am we were the only customers - there wasn't even a pot of coffee on the burner. It was a cozy, old-fashioned café with booths and a long lunch counter, decorated for the holidays with tinsel and poinsettias. We stopped for brunch at the Roseland neighborhood's S & E Diner, 11117 South, where signs told us the building was for sale. At 119th we crossed the Major Taylor Trail bike path, named after the black man who dominated bicycle racing at the turn of the 20th Century. We passed the Cedar Park Cemetery, the Halsted Bowl bowling alley and the Jetsonian Kleen Towne Cleaners building. Here the concrete was covered with a grainy slush that was easier to walk on than the glare ice we encountered up north and Kevin, half a foot taller than me, set a brisk pace. Virtually everyone we'd encounter for the next 90 blocks was African-American. Halsted became a four-lane street with parking, left-turn bays and sidewalks lined with storefront churches, day-care centers, barbershops and Harold's Chicken shacks - we counted three within a seven-mile stretch. As we crossed into the city the scenery suddenly changed from rural to urban. At the apex of the bridge I found a bootleg CD of Atlanta rapper Gucci Mane's album "Trap-A-Thon" lying in the snow and we shot a self-portrait with the water behind us. On the way to the bridge over the river we passed the Riverdale Marina where a couple of yachts hibernated at the dock. At 10am, after ducking behind trees to pee, we began our march. There were no sidewalks here and wooded areas on either side. We were just south of the Little Calumet River, Chicago's southern border. An hour and a half later Pace Bus 352 dropped us off at 130th and Halsted in the village of Riverdale, between Whistler Forest Preserve and the Joe Louis "The Champ" Golf Course. An ice storm hit the night before and the sidewalks of our neighborhood, Humboldt Park, were glazed and treacherous as we made our way to the CTA Blue Line. 9, long after the temperature had dropped below freezing and several inches of snow had fallen. This fall I persuaded my buddy Kevin Monahan to join me on this excursion, but we kept procrastinating until Sunday, Dec. The highway ends at the Kentucky border by Cave-in-Rock State Park, which used to be a hideout for Ohio River pirates. Early on, Halsted was referred to as the Egyptian Road because it eventually made its way to southern Illinois, known as "Little Egypt." Today Illinois Route 1 follows the street from I-57 at 99th Street far into the south suburbs. Later it was renamed after William and Caleb Halsted, brothers and bankers from Philadelphia who helped Chicago Mayor William Ogden finance his real estate ventures. If I could complete the 20-mile stretch in a day it would be the longest walk of my life.Īccording to Streetwise Chicago by Don Hayner and Tom McNamee, Halsted was originally named First Street, then Dyer Street in honor of Charles Volney Dyer, an abolitionist who aided hundreds of freedom seekers on the Underground Railroad. Halsted is shorter than Western, but with less car lanes and slower traffic it's also a more walkable street and perhaps a more interesting one. It runs through Chicago from 129th Place in gritty West Pullman, a working-class, black neighborhood, to Grace St., 3800 North, in gentrified Boystown, the center of gay life in the city.
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I decided it was time to take on Halsted Street, one of our most famous and varied thoroughfares.
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When Time Out Chicago recently did a special on Western Avenue, one of the world's longest streets, it reminded me how satisfying it was to complete those urban hikes. Walking an entire street is a great way to get a feel for the vastness of our town and to experience its architectural, economic and cultural diversity. A few years later I followed Western Avenue from Blue Island to Evanston, about 24 miles, over the course of two days. Back in '95 I strolled Milwaukee Avenue from the West Loop to the suburb of Niles, about 11 miles. But I have taken some epic hikes in the city. I don't walk much in Chicago most of the time I ride a bicycle or take transit.