Overview Old Town Oktoberfest is a three-day street festival on Wells Street in Chicago's Old Town, which its hosts call the city's first German neighborhood, with stein-holding contests between band sets, football on a giant outdoor screen and a Sunday dog parade with three entry classes: Wee Wieners, Pretzel Pups and Big Bratwursts. It runs over a mid-September weekend, Friday evening through Sunday, centered at 1360 North Wells. The Old Town Merchants and Residents Association, the neighborhood's chamber of commerce and community development nonprofit, hosts it, and Special Events Management produces it. The 2026 festival was its second. The same association runs the Wells Street Art Festival every June. On site The food is bratwurst and pretzels and the beer is German. In 2026 the stage ran Friday 5 to 10, Saturday 11 to 10 and Sunday 11 to 8, with the Four Star Brass Band playing both Friday and Saturday, Hello Weekend and Second Hand Soul Band, the Funky Monks closing Saturday with Red Hot Chili Peppers covers, and a Sunday of School of Rock students, the Bratwurst Brothers, live band karaoke and Stache. Masskrugstemmen, the Bavarian stein-holding contest, ran up to four times a day for prizes. The dog parade stepped off at 11 on Sunday morning for its first year in 2026, with dogs sorted by weight: under 30 pounds, 31 to 70, and over 71. Brand presence Special Events Management sells sponsorship directly as custom packages at top, mid and entry levels, and pitches the festival to brands looking to reach active consumers. Vendors apply separately and are not given category exclusivity.