Best of the South Side 2008: Woodlawn

In 1893, the World’s Columbian Exposition brought economic prosperity to Woodlawn. Unfortunately, it left economic hardship in its wake that would persist for much of the next century, especially as a sudden racial succession turned the neighborhood from 87% white in 1930 to 89% black in 1960. Racial issues and class tensions, particularly with its northern neighbor the University of Chicago, only exacerbated its economic problems, and admittedly they’re far from resolved, even today. With the school’s continued expansion south of the Midway Plaisance, these issues will only continue to influence the identity of the neighborhood. But whatever its future may hold, there’s much to appreciate in this historic area.

Best Bikeshop
Blackstone Bikes
Some bike shops have lousy owners who treat you like shit and then charge you an arm and a leg for basic repairs. Blackstone Bikes is no such bike shop. And with Tati essentially closed for business, Blackstone is pretty much the only morally acceptable option in the area left. And I don’t use the term “morally” lightly–these guys are as focused on helping neighborhood youth as they are on fixing your bike at reasonable prices. They don’t just teach bike basics, either. They also offer advice on running a small business, and like to incorporate volunteers into all levels of their operation to give hands-on experience. While other shopowners bitch at you for bringing them service, these guys hold workshops to teach you how to do repairs yourself. But what else would you expect from a non-profit organization? Seriously, this one’s a real no-brainer. 6100 S. Blackstone Ave. Tuesday-Friday, 1pm-5pm; Saturday, 12pm-5pm. (773)241-5458. (Sean Redmond)

Best Place to Get Jerked Around
Jamaican Jerk Spice
Founded by a former employee of Richard’s (a more established Jamaican joint in Woodlawn, on 61st and Prairie), Jamaican Jerk Spice offers a Spartan atmosphere, Styrofoam plates, and delicious Caribbean nourishment. Jerk chicken and pork are staples, obviously, but so are curried goat, imported Jamaican sodas, and plantains, prepared to order. The place has the look of a miniature cafeteria, and all the sides are a la carte. A meal can get a bit pricey (I forked over $8), but lunch is a better deal–probably the reason why the place is popular with Woodlawn locals. And like most establishments in Woodlawn, it’s cash-only. 6500 S. Cottage Grove Ave. (773) 955-4333 (Lisa Bang)

Best All-Purpose Facility
Experimental Station
The Experimental Station was born from the ashes of a 2001 fire that destroyed a building used by artist Dan Peterman for his socially conscious art projects. The Experimental Station’s organizers picked up that legacy and ran with it. Today it is a hive of progressive and artistic projects, ranging from tenants like Blackstone Bikes and Backstory Café to more transient uses like Jamie Kalven’s Local Human Rights Documentation Project. This summer, the Experimental Station has hosted a reading by Thomas Frank (author of “What’s the Matter with Kansas?”), a series of beginning bike mechanic classes, and a performance by DJ Kool Herc, not to mention a weekly farmers market that’s working to fix the Woodlawn food desert. 6100 S. Blackstone Ave. (773) 241-5458. (Sam Feldman)

Best Comfort Food
Around since immigrant laborers needed lunch in the 1930s, Daley’s has weathered the massive changes to Woodlawn it has seen pass. Not only does its lengthy history give it a perspective few institutions on the South Side can match, it also gives Daley’s solid recipes for everything from pancakes to hamburgers. The history is as thick as the grease; it’s also as thick as the ties that bind Woodlawn together 6307 S. Cottage Grove Ave. Monday-Sunday, 7am-10pm. (773)643-6670 (John Thompson)