Bridgeport and Bronzeville are two of the oldest and proudest South Side neighborhoods. This route, which weaves through the historic neighborhoods, is a great one for both casual and experienced cyclists alike.
I start off at the Reg, taking 57th Street north to Ellis Avenue and then Ellis north to 53rd Street, before heading west two blocks to Drexel and again turning north. Once past 51st Street heading north on Drexel, the road opens up into a beautiful boulevard, where a 15–yard wide patch of grass sprinkled with trees divides the southbound and northbound lanes. Drexel Avenue is part of a large boulevard network in Chicago, featured on other nearby streets like the Midway, King Drive, and Garfield Boulevard, as well as other boulevards that can be seen throughout the city. The boulevard system in Chicago was built in 1849 in an effort to beautify the city. Today they continue to serve that function well.
Along with the beauty of the boulevard, Drexel is great to bike on, as it is equipped with a bike lane. I head north on Drexel until it ends at Oakwood Boulevard, passing by some impressive architecture. including Victorian mansions and row houses, Martin Luther King College Prep, a magnet high school, and Grant Memorial Methodist Church. I take a left onto Oakwood, also equipped with a bike lane, and as I head west I am moving from the west edge of Kenwood further into Bronzeville
After three short blocks on Oakwood, I turn north again on King Drive, a busy South Side thoroughfare that also conveniently has a bike lane. I pedal north to 35th Street where I take a left and head west. Thirty-fifth Street does not have a bike lane, but is a wide street with only one lane of traffic each way and is bike friendly. The headquarters of the Chicago Police Department are located just five blocks west in a new white building with blue windows. As I continue west, I pass under the Green Line and through the campus of the Illinois Institute of Technology. I carefully cross over the Dan Ryan expressway, crossing from Bronzeville into Bridgeport. As I continue west, the tan stone and black roof of US Cellular Field towers to my left. “The Cell,” as it is more affectionately known, houses the Chicago White Sox. Some Sout Side purists still refer to the stadium as “Comiskey Park”, after the late owner of the Sox from 1900–1931, Charles Comiskey, for whom the stadium was originally named.
Further west on 35th are two Bridgeport staples. The first is Grandstand Sports, home to any type of sports paraphernalia a Chicago sports fan could ever possibly need or want. The second is Morrie O’Malley’s, a shack of a hot dog joint on the corner of 35th and Union, that serves a mean Chicago dog and some great soft serve in the summer. I continue west to Halsted Street, saving my stomach for another foodie stop down the road. I head north on Halsted, one of Chicago’s most famous north-south streets. Halsted is equipped with a bike path, but can be heavy with traffic.
I head north on Halsted to 29th Street, where I turn left and venture onto a paved trail at Stearns Quarry Park. The path takes me up a grassy hill for some great Chicago views. Past the Stevenson and Dan Ryan Expressways with Pilsen coal plants in the foreground, one has a clear look at the towering downtown skyline and the pristine lake.
As I take the path down on the north side of the hill I am led back to Halsted, but not before I pass by what is now a wetland habit that still resembles the limestone quarry it functioned as in the 1930s.
I cross Halsted at the northeast end of the park and head onto residential 26th Sstreet. Even in the off-season, Bridgeport residents take pride in their local baseball, as Sox flags fly from the porches of many houses. The area is also home to large Irish population, as many Irish immigrants moved to this area of Chicago in the late 19th and early 20th centuries, so Irish flags are often flying, as well. I take 26th to Canal Street where I turn south, rolling through rows of houses until I hit 31st Street. On the southeast corner of the intersection is my foodie destination, the Maxwell Street Depot. Open 24/7, “The Depot”, a one–room grill with a walk-up window, serves grease accompanied with sandwiches, fries, and fried onions. I pull over and wolf down a Polish sausage before hopping back on my two-wheeler.
Having circled through Bridgeport, I head back east to Bronzeville on 31st Street. Thirty-first does not have a bike lane but does not have much traffic. Before crossing the Dan Ryan back into Bronzeville, I stop at Ferro’s Restaurant on 31st and Wentworth. Though I do not have room left for their specialty Italian sausage, I grab some of their delicious Italian ice for dessert. I have a scoop of both lemon and strawberry, which hits the spot.
A half–mile further east on 31st and I run into King Drive again and take it back south. Cruising south in the MLK Drive bike lane, I pass through the heart of Bronzeville. At the corner of 35th and King I pass Mississippi Rick’s to my left, a jerk chicken–lover’s paradise. From there I continue on King, another beautiful tree-sprinkled boulevard, all the way south to 51st Street, before veering southeast onto Elsworth Drive. Elsworth winds through Washington Park, where cricket and baseball teams are still out playing in the vast fields to my left. I take Elsworth to Morgan Drive where I take a left, passing by the DuSable Museum of Africam American History to the east, before taking a left onto 57th Street and heading east back to campus.
In that short hour and a half ride I hit a ton of great locations, but there were many that I missed as well. That really is the beauty of the city: there is a unique story around every corner.
Care to join me or have ideas for future routes? Email email@example.com.