If you live in Old Town, you already know the drill. Wells Street closes off in mid-June, tents go up along Lincoln and Wisconsin, and half the neighborhood spends a weekend wandering through paintings, ceramics, and a garden walk that gets you into backyards you'd otherwise never see. You call it the art fair. Everyone does.
What most residents don't clock is that they're actually watching two separate events, staged by two separate organizations, on the same weekend, a few blocks apart. One is run by a historic preservation nonprofit. The other is run by the neighborhood's business association. Neither reports to the other. And once you notice the split, the rest of Old Town's calendar this year, plus the wave of new restaurants filling in behind it, starts to look a lot less like a random collection of good news and a lot more like two different visions of what this neighborhood is for, playing out on the same six blocks of Wells Street.
The One Everyone Knows
The 2026 Old Town Art Fair was scheduled for June 13 and 14, with gates at Lincoln and Wisconsin, ten to seven on Saturday and ten to six on Sunday, rain or shine. It's in its 76th year, which makes it one of the older continuously run art fairs in the city, and it's organized entirely by volunteers under the nonprofit Old Town Triangle Association. More than 200 artists get juried in by a panel of gallery owners, curators, and working artists, and the fair draws an estimated 30,000 to 35,000 people over the two days, depending on which year's recap you read.
The part locals actually love, though, is the Garden Walk: a self-guided tour through more than 50 private gardens tucked behind the Triangle's historic homes, open for exactly this one weekend a year. That detail matters, because the Old Town Triangle Association isn't a merchants' group trying to drive retail traffic. It's the organization tasked with protecting the historic district itself, including the landmarked homes on West Burton Place where artists Edgar Miller and Sol Kogen spent the late 1920s converting deteriorating Victorians into sculpted, mosaic-tiled studio apartments. The fair is rooted in this historic district and is a separate event from the Wells Street Art Festival.
The One Happening at the Same Time, a Few Blocks Over
Here's the part that gets lost. The Wells Street Art Festival is a separate event from the Old Town Art Fair, typically landing on the same weekend, and it's organized by the Old Town Merchants and Residents Association, not the Triangle Association. OTMRA functions as the neighborhood's chamber of commerce. The Wells Street Art Festival takes place among the shops, restaurants, and bars that line Wells Street itself.
So for one weekend in June, Old Town effectively runs two art fairs with overlapping names and adjacent footprints, each answering to a different institution with a different job. The Triangle Association's fair is held in the historic district; the merchants association organizes a separate festival on Wells Street. If you've ever wondered why the fair seems to sprawl further than you remember, or why some vendors feel like they belong to a different event entirely, that's why. You're not misremembering. You're looking at two fairs stitched together by proximity, not by design.
OTMRA's New Idea for the Rest of the Year
The merchants association didn't stop at one festival. Old Town Oktoberfest debuted on Wells Street in September 2025 and returns September 19 through 21, 2026, complete with bratwurst, pretzels, live traditional music, and Masskrugstemmen, the stein-holding endurance contests that have become the event's signature. OTMRA lists the Wells Street Art Festival and Oktoberfest together as its two signature street festivals, one in June and the other in September.
Oktoberfest is a new event in a neighborhood with a long German history. Old Town was Chicago's first German neighborhood, settled by German farmers whose truck gardens earned the area its old nickname, "The Cabbage Patch." Oscar and Gottfried Mayer opened a small butcher and sausage shop on Sedgwick Street in 1883 that eventually became Oscar Mayer. Founded in 1888, the House of Glunz on North Avenue is still the oldest family-owned wine shop in the country, started by a German immigrant. That history predates the festival.
A French Afternoon Wedged in the Middle
There's a third thread, smaller than the other two but worth knowing if you live here. In 2023, Old Town and Montmartre in Paris became officially twinned neighborhoods, building on Chicago and Paris's status as Sister Cities since 1996. The connection shows up every mid-July, when Old Town hosts a Bastille Day celebration with cabaret, film screenings, and French-themed offerings across local venues and wine tastings.
It's a lighter touch than the June fair or the September festival, no street closures, no vendor tents, but it completes a pattern worth naming: Old Town now has a dedicated calendar day for its German settler history, its French sister-neighborhood bond, and its American art-colony roots, and each one belongs to a different organizing body or civic relationship rather than being folded into a single generic "neighborhood festival."
Two Organizations, Two Parts of Old Town's Calendar
Step back and the split becomes the actual story. The Old Town Triangle Association exists to protect a historic district and uses its fair to fund and showcase that mission, right down to the Garden Walk giving people access to private, landmarked yards for one weekend a year. The Old Town Merchants and Residents Association organizes its own festivals, while Special Service Area 48 funds streetscape maintenance and public art along Wells Street.
The two organizations are involved in different parts of Old Town's civic life. If you live closer to the Triangle's residential streets, your summer revolves around garden gates and historic home tours. If you live along or near Wells Street itself, your summer revolves around which restaurant just opened and whether the sidewalk in front of it is roped off for a festival again. Both halves are true at once, and that's precisely why a single "what's happening in Old Town" roundup tends to flatten a neighborhood that's actually running two separate civic operating systems in parallel.
The Storefronts Are Catching Up to the Calendar
The restaurant openings this year track the same divide. A few notable additions to the Wells Street corridor in 2026:
- FARE, a healthy-food concept with several existing Chicago and North Carolina locations, is opening at 868 N. Wells Street sometime this summer.
- L Station Chophouse, from restaurateur Le'Roy Patterson, is bringing a steak-forward menu with a Miami and Las Vegas dining sensibility to 455 W. North Avenue.
- SHŌ Omakase opened in August 2025 and has already been named a 2026 semifinalist for the James Beard Award for Best Chef in the Great Lakes region, a fast validation for a restaurant barely a year old.
All three are landing within a few blocks of Old Town's legacy anchors: the House of Glunz on North Avenue, Kamehachi, widely credited as Chicago's first sushi restaurant, Marge's Still, the oldest bar in the city, and The Fudge Pot, the candy shop whose owner also happens to be OTMRA's current president. Together, these openings and longtime institutions give the corridor a mix of old and new.
The One Thing That Doesn't Need a Festival Weekend
Underneath both organizations' calendars sits something that doesn't rotate with the seasons at all. The Second City, at 1616 N. Wells Street, keeps running its Mainstage revue and its e.t.c. stage year-round, with its 114th Mainstage revue cast announced earlier this year and its Victor Wong and Bob Curry Fellowship showcases scheduled on the e.t.c. stage through May and October 2026. Zanies Comedy Club sits nearby on the same corridor. Neither venue needs a street closure or a merchants' association calendar to justify its existence. Comedy has simply been part of Old Town's identity since the artist-colony days of Edgar Miller and Sol Kogen turned this stretch of Wells Street into a creative enclave in the first place, and it's the one thread that doesn't need an organizing committee to keep showing up.
Why This Matters If You Already Live Here
None of this changes whether you should move to Old Town. You already live here. What it changes is how you read your own neighborhood's calendar. The next time Wells Street closes for a weekend, it's worth checking which organization is organizing the event: the Triangle Association or the merchants association. They're not competing exactly, but they're not the same project either; restaurant openings, festival dates, and streetscape upkeep are distinct parts of Old Town's story. Watching the festival calendar, storefront turnover, and foot traffic tells you more about where this neighborhood is heading than any single "new restaurant" headline ever could.
If you're curious how that kind of shift, more commercial energy on Wells Street, a growing fall festival calendar, chef-driven openings landing next to century-old anchors, tends to show up in what buyers are willing to pay for a home near that corridor versus one tucked into the quieter Triangle side streets, that's the sort of block-by-block read Julie Latsko tracks across Old Town and the rest of central Chicago. No pressure to do anything with it. Just useful to know your neighborhood a little better than the last person who wrote about it.
