Old Town Community Events

Chicago has long been considered a city of neighborhoods. Few manage to bridge cosmopolitan and community, neighborhood and nightlife, quite like Old Town, where charming townhouses share real estate with some of Chicago’s most enduring pop culture institutions.

That’s why Old Town Community events run the gamut — sprawling festivals that cover blocks and draw thousands to more intimate affairs.

Ya Gotta Have Art

When it comes to events in Old Town, few are more confusing than the concurrent Original Old Town Art Fair in the Old Town Triangle District and the Wells Street Art Festival a few blocks south of the triangle. They share the same June weekend and an artsy inclination.

But there are differences between the two. The Old Town Art Fair, considered one of the best in the country, celebrated its 70th anniversary in 2018. It draws roughly 30,000 visitors over two days, shows more than 250 artists, includes a garden walk showcasing about 50 private gardens in the neighborhood and charges $10 for adults.

The Art Festival is roughly 25 years younger. It runs to 10 p.m. (Old Town closes at 7 p.m. on Saturday and 6 p.m. on Sunday), more in keeping with its bar- and restaurant-lined locale, features 225 artists, draws slightly bigger crowds, and seeks a “suggested donation” of $7.

Small Can Be Better

The Old Town Merchants & Residents Association keeps the neighbors engaged with small events throughout the year. For example, the 2018 schedule included Old Town Restaurant Week in February; Old Town Theater Week in March; a July networking event co-sponsored with the chambers of commerce from neighboring Lakeview, Lincoln Park and Roscoe Village; a social media seminar series in July and August; a summer social; and September’s Night Out in Old Town.

Appointments in the Park

Lincoln Park, the green space, sits at the eastern edge of Old Town, while Lincoln Park, the neighborhood, is just to the north. Both are easy destinations teeming with events, including:

  • Chicago Sprints Regatta in Lincoln Park Lagoon, one of the largest rowing regattas in the Midwest.
  • Lincoln Park Greek Fest, at St. George Greek Orthodox Church, is entering its fifth decade of serving Greek street foods, sweets and specialty plates along with traditional and modern Greek music, pop music, dance troupes, kids activities and tours of the 95-year-old church.
  • Taste of Lincoln Avenue began as a neighborhood fundraiser in 1984, growing into an event attracting upward of 50,000 attendees over two days. The late-July event in 2018 featured more than 250 purveyors and 30 musical acts, as well as special chocolate, wine and whiskey tastings.