Vincent in Andersonville

Night music at Wicker Park Fest

A few blocks from the Western stop on the Blue Line on the neighborhood’s northern edge, get the engine going at Ipsento (2035 N. Western Ave., 773-904-8177; items from $3) with the namesake latte, which blends espresso and milk with coconut milk, honey, and cayenne. As you head south, stop at Belly Shack (1912 N. Western Ave.; 773-252-1414), which now sells soft serve by the cup ($4) in flavors such as huckleberry lime and bacon chocolate chip; order some togarashi-spiced fries ($3) while you’re at it. If you take Milwaukee Avenue, you’ll soon encounter Irazú (1865 N. Milwaukee Ave., 773-252-5687; entrées from $9.50), a Costa Rican BYO whose oatmeal shake has something of a cult following. Retreat to the lush patio and order the chifrijo, an appetizer of black beans, fried pork belly, pico de gallo, and rice, best shoveled in with chips. You’ll pass Park No. 529 at Wabansia Avenue and Leavitt Street, a tiny slice of a park that seems to attract an inordinate number of handsome young men playing with their dogs. Stop there to rest, or plant yourself on a shady bench at the Bucktown–Wicker Park Public Library (1701 N. Milwaukee Ave.; 312-744-6022).

At Six Corners—the frenetic intersection of North, Milwaukee, and Damen Avenues—several excellent alfresco dining options are within striking distance. Ripasso (1619 N. Damen Ave., 773-342-8799; entrées from $14) serves handmade pastas and can open the three large French doors in its dining room to the street. Birchwood Kitchen (2211 W. North Ave., 773-276-2100; entrées from $6.80) does brunch and burger specials on weeknights and has an adorable backyard patio. Bake (2246 W. North Ave., 773-384-7655; items from $2) is a bakery and café with a quiet garden where you can sit and sip. Lillie’s Q (1856 W. North Ave., 773-772-5500; entrées from $8) serves some of the city’s best barbecue and offers sidewalk seating on quieter Wolcott Avenue. The large and inviting side patio at The Southern (1840 W. North Ave., 773-342-1840; entrées from $7) is a bourbon-steeped oasis on a hot day.

On July 28 and 29, the Wicker Park Fest takes over Milwaukee Avenue from North Avenue all the way to Wood Street; this year’s big acts include Kill Hannah, Joe Pug, and Lucero, a punk-country band from the South. But the neighborhood’s alfresco pièce de résistance is, naturally, Wicker Park itself. The iconic triangular swatch of greenery was made nearly irresistible once Paul Kahan set up his gourmet taco shop, Big Star (1531 N. Damen Ave., 773-235-4039; tacos from $3), less than a block away. Carry out your pork-belly-filled taco de panza ($3) and guacamole ($8) and picnic away. On Sundays from 8 a.m. to 2 p.m., fortify your meal with fruits and baked goods from the Wicker Park farmers’ market, which sets up at the intersection of Damen and Wicker Park Avenues. Nearby, keep summer rolling at Nick’s Beer Garden (1516 N. Milwaukee Ave.; 773-252-1155), where the large patio stays open until midnight on weekends.

Photography: Courtesy of Wicker Park Fest