The perfect Bridgeport bike ride
Nothing puts me in the mood to bike like the fall. Colder weather makes me think of the coming winter. I get FOMO and take out the bike.
But where to go? Let me suggest a place with history, good views, and mellow residential streets ideal for biking. Let me share my perfect Bridgeport bike ride.
(Depending on your speed, this 3.3-mile ride could take around a half hour.)
Palmisano Park
The tour begins at Palmisano Park, at 27th and Halsted. The hill there has one of the best views of the skyline. A former quarry and then a trash mound, the city turned it into a park in 2009.
This park, with its prairie grass and a fish-stocked pond, is a great entry point for Bridgeport, one of the city's oldest neighborhoods. Bridgeport is home to immigrants, artists and some of the most old-school Chicagoans you’ll ever meet. Its name comes from river barge captains forced to unload their cargo at the Ashland Avenue bridge because it was too low to the river.
I lived a block west of Palmisano Park when I moved to Chicago 12 years ago. Back then, Palmisano was my go-to spot — for a picnic, and for the Fourth of July, when crowds would gather to catch 360-degree views of fireworks across the city. It was also my scenic cut-through to the Orange Line’s Halsted station.
That station is a great way to get to the neighborhood, if you’re coming from far away. You could also bike Halsted Street itself. The street recently got decent bike lanes, stretching up to Greek Town and down to 59th Street.
Next, let's head east on 29th Street.
Impallaria Bakery and Deli, 2952 S. Wallace St.
Turn south on Wallace and reach Impallaria Bakery. This old-school Italian bakery churns out zeppole for Saint Joseph’s Day. The eclairs are my mom's favorite.
As you continue south, notice how some homes appear sunken below street level. They were built before the city raised its streets and downtown in the mid-1800s to allow for sewers. As we cross 35th Street, notice Rate Field, current home of the White Sox, to the east.
Daley House, 3536 S. Lowe Ave.
No tour of Bridgeport would be complete without acknowledging "Hizzoner's" longtime family base. This bungalow is the home of former mayor Richard J. Daley. It’s where his family raised seven children, including former mayor Richard M. Daley. Now it's the home of his nephew Patrick Daley Thompson, former 11th Ward alderman.
Ramova Theater, 3520 S. Halsted St.
Crossing Halsted, you'll notice the theater's big neon sign. This block had little going on years ago. But that changed when a group of local investors revitalized this old theater into a concert venue. Across the street is Electric Funeral, a punk-themed bar with colorful drinks owned by the same people behind the cafe that ends this tour.
Bridgeport Arts Center, 1200 W. 35th St.
This gigantic former warehouse on the banks of Bubbly Creek is home to dozens of artist studios, a Maritime Museum, a wedding reception space and cafe. I recommend visiting during "3rd Fridays," a monthly open house. I’ve enjoyed evenings here getting lost in the five stories and stumbling into artists studios where they offer wine and conversation.
St. Mary’s Catacomb Cafe, 1039 W. 32nd St.
Who can pass up a self-serve, donate-what-you-can cafe in the basement of one of Bridgeport's oldest churches (it was completed in 1892)? It's spacious, decorated with biblical figurines, and a patio. But the hours are limited: Thursday to Saturday for non-parishioners.
Continue east on 32nd Street.
UrbanLab, 3209 S. Morgan St.
This spot, with its rusty steel outer wall, is a home and workspace of architecture firm UrbanLab. Founders Sarah Dunn and Martin Felsen built it on the site of a former grocery store. Look through the fence to see the mound of debris this structure is built into. UIC professor Stewart Hicks has an excellent video tour of the site on YouTube.
Co-Prosperity Sphere, 3219 S. Morgan St.
This art gallery is, in my opinion, the cultural and artistic heart of the neighborhood. I've witnessed art shows, a drag show and a vinyl record sale there. It’s HQ to the Public Media Institute, which runs Lumpen FM (105.5 FM) from inside. The radio station was co-founded by Ed Marszewski, the son of Maria from the famous Maria's Packaged Goods up the street.
Head east on 32nd Street. Stop at Halsted's crosswalk. Just to the south is where city planner Riley O’Neil was fatally struck by a driver.
O’Neil worked in the city transportation department’s Complete Streets program, which redesigns roads to make them safer for pedestrians, cyclists and drivers.
Jackalope Coffee and Tea, 755 W. 32nd St.
Our tour ends with cheap coffee and sandwiches on a cul-de-sac. It’s punk, it’s colorful, it’s named after a mythical antlered rabbit. Jackalope is my favorite spot in the neighborhood to sit, read and work.
Tell us what you think! Did I miss your favorite spot or street? What neighborhood should I tour next? Write me at [email protected]
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