Retro on Roscoe

Retro on Roscoe

The alfresco action centers on the section of Roscoe Street between Damen and Western Avenues. Approach the bustle by passing under the Metra tracks on Roscoe. During the warm-weather months, three big street festivals set up shop on this strip: Burger Fest ( on July 21 and 22, with a best-burger competition that festival goers vote on; Retro on Roscoe ( in August, one of the city’s largest summer street events, with some of the best music; and Oyster Fest at the end of the season in September, where oysters can sometimes be hard to find (drown your sorrows in beer—namely, Guinness, Harp, or Smithwick’s).

Otherwise, working west, duck into Four Moon Tavern (1847 W. Roscoe St., 773-929-6666, entrées from $8.25), a neighborhood bar with above-average food, a great beer list, and lots of tables outside. On the south side of the next block, look under your feet—the sidewalks are often decorated by a local artist who lives there. Pass through the campy interior of Kitsch’n on Roscoe (2005 W. Roscoe St., 773-248-7372; entrées from $6.99) and make your way to the back patio, which offers comfort food in a pleasant cloister. Across the street, sip wine and nestle in the nooks of the hidden patio at Volo (2008 W. Roscoe St.; 773-348-4600). On a hot day, check out the raucous beer garden at Village Tap (2055 W. Roscoe St.; 773-883-0817). Vegetarians should try Victory’s Banner (2100 W. Roscoe St., 773-665-0227; entrées from $6), which has hearty fare that even meat eaters enjoy; go for its homemade veggie burger from the bricked patio. At the trellised sidewalk area at Turquoise (2147 W. Roscoe St., 773-549-3523; entrées from $14), dine on some of the city’s best Turkish food.

Picnickers should grab sandwiches, served with smiley counter service, from Nohea Café (2142 W. Roscoe St., 773-935-7448; entrées from $7.50). Cubanos are the ticket at 90 Miles Cuban Cafe (3101 N. Clybourn Ave., 773-248-2822; sandwiches from $7), which also runs a small patio with piped-in music. Take your goodies to Fellger Park (2000 W. Belmont Ave.; 312-742-7785), where swarms of children animate the playground equipment, swings, lawn, and spray area. Past Western Avenue’s multitude of strip malls, hike along the bowered riverfront path in Clark Playlot Park (3400 N. Rockwell St.; 312-742-7594) for a soothing but short half mile. Bring your off-road bike to hit the dirt jumps in The Garden, a haven hidden in the woods.

Just outside of Roscoe Village, stop off at Scooter’s Frozen Custard (1658 W. Belmont Ave., 773-244-6415; cones from $2.99), a great neighborhood institution, for a large scoop of anything on the menu—because, after all, summer in Chicago hasn’t truly started until ice cream drips down your arm.