Start and end Orange Line, Halsted stop
Walking time 4 hours Distance 3.9 miles
1 Bridgeport’s best known for red-brick bungalows and blue-collar bars, but you’ll also find a surprisingly vibrant patch of greenery. Take in the scene at Stearns Quarry Park (2700 S Halsted St), where you can climb up the 35-foot hill for rockin’ views of the skyline. To get there, exit the station, cross Archer Avenue and walk south on Halsted Street. The former garbage dump turned 27-acre oasis opened in May with hiking trails, a tranquil pond and native plants, plus a fishing pier that’s in the works. Just try not to think about the landfill under your feet.
2 Walk four blocks south and one block east on 31st Street to grab a big, tasty burrito at Pancho Pistolas (700 W 31st St, 312-225-8808) or keep going south on Halsted for blynai (a.k.a. potato pancakes) at the inaccurately named Healthy Food (3236 S Halsted St, 312-326-2724), a heavy-on-the-meat Lithuanian restaurant.
3 Keep walking east from Pancho’s to the Orphanage (643 W 31st St, no phone; $5), a groovy, artist-run performance space and gallery in a church community center. One of Bridgeport’s best-kept secrets, the Orphanage hosts concerts and art shows every Sunday night.
4 Looking for spell-casting herbs, oils or candles? Head back to Halsted and walk south to Augustine’s Authentic Spiritual Goods (3327 S Halsted St, 773-843-1933). The occult store was located across the street until the city confiscated the property under eminent domain. Rumor has it the original owners cursed the old site—which is now occupied by the Ninth District police station. A few doors down from Augustine’s, action-figure emporium Monster Island Toys (3335 S Halsted St, 773-247-5733) offers a different kind of magic: Godzilla makes a personal appearance there Sunday 6, 11am–1pm.
5 Detour one block north on Halsted for a cold one at Bernice’s Tavern (3238 S Halsted St, 312-907-1580). Locals recommend this low-key bar for its live music and bingo nights. We love owner (and self-taught artist) Steve Badauskas’s kinetic sculpture The All-Inclusive Towering Town, a symbolic homage to Bridgeport that appeared in a recent show at the Chicago Tourism Center.
6 Drink enough to brace yourself for the sad state of the Ramova Theater (3518 S Halsted St), three blocks south on Halsted. Only rats and pigeons now manage to get inside the Music Box’s once-gorgeous sibling, a 1,200-seat theater that opened in 1929, but you can still sigh over its Art Deco marquee and elaborate “Spanish Renaissance” facade. It closed in the mid-1980s, but in 2005 Save the Ramova, a group affiliated with Preservation Chicago, began prodding the city to rehab the building.
7 Keep going three blocks west on 35th Street and turn north on Morgan Street to visit the epicenter of the Bridgeport Art District: Co-Prosperity Sphere (3219–21 S Morgan St, 773-837-0145, coprosperity.org), which has an irregular but active exhibition schedule. The gallery’s proprietor, Ed “Edmar” Marszewski, also runs multimedia arts showcase Version Fest. Across the street, the apartment gallery Second Bedroom (3216 S Morgan St, apt 4R, 630-849-7750, secondbedroomproject.blogspot.com) opens one Friday per month and by appointment. Walk south to 35th Street and head west to the Zhou B Art Center (1029 W 35th St, 773-523-0200, zbcenter.org), which contains studios, galleries and a cute café.
8 Half a block west on 35th Street, turn on Aberdeen Street and walk four blocks north to the Monastery of the Holy Cross (3111 S Aberdeen St, 773-927-7424, chicagomonk.org), a monastery and popular bed-and-breakfast run by Benedictine monks whose Gregorian chants can be heard outside several times a day.
9 If spiritual sustenance leaves you craving croissants, stroll half a block east to Bridgeport Coffee House (3101 S Morgan St, 773-247-9950), which roasts its own beans and offers free Wi-Fi. Take in enough carbs for the trek back to the CTA; the safest route runs a few blocks east to Halsted, then north to where you began.