The Old Town Art Fair occupied the streets around the Old Town Triangle Center on June 13 and 14, with more than 200 juried visual artists and a $13 suggested donation at the gate. It is among the oldest outdoor juried fairs in the country, set inside a landmark district of Victorian houses on curving streets that the grid never managed to straighten out.
The art is good and the jury is real. But the fair’s most interesting element is the one it treats as an accessory: the garden walk.
The Sleeper Attraction Is the Actual Attraction
Private gardens, in a dense landmark district, opened to strangers for two days. This is a form of exhibition, and a more demanding one than a tent full of framed prints, because a garden cannot be hung, lit or curated into coherence by anybody other than the person who has been tending it for thirty years. One is looking at a decade of accumulated decisions in a space the owner cannot rearrange for the occasion.
Posted 2026-06-16
From the postWe had an absolute blast at @oldtownartfair in Chicago! Thank you to the show organizers and the thousands of people that showed up to support the arts! This ended up being our best show ever and Chicago continues to…
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It is also the only part of the weekend where the neighbourhood itself is the object under examination rather than the venue. The Old Town Triangle survived the Fire, survived urban renewal, and was landmarked before most of Chicago understood what landmarking was for. Walking through its back gardens is a more instructive experience than anything in the aisles, and the fair charges nothing extra for it.
Two Hundred Artists Is a Lot of Artists
A word on scale, since it recurs across every fair in this city’s June. Two hundred juried booths is more work than any visitor can actually look at. The same is true of the Gold Coast Art Fair with its own 200-plus, and of the Wells Street Art Festival running the identical weekend a few blocks west with over 100.
Posted 2026-06-13
From the postBeautiful weather here at the Old Town Art Fair in Chicago and two paintings with new homes!
Three art fairs within walking distance of one another on one June weekend, each presenting more objects than a person can absorb. The result is not abundance. It is a visitor moving at a pace that makes genuine looking impossible, which is precisely the condition that fairs of this scale create and then describe as success.
The corrective is to refuse the itinerary. Pick one fair. Spend the morning in perhaps fifteen booths. The the published calendars lists all of them, which is useful for knowing what to skip.
Posted 2026-06-13
From the postNew work showing at Old Town Art Fair in Chicago. Love this city!
Old Town also hosts the Ginza Holiday Festival at the Midwest Buddhist Temple in August, an event with considerably more history beneath it than this one and a fraction of the attention. The neighbourhood is better at this than its reputation suggests.
When the aisles thicken after lunch, find the garden-walk map, and stand in the smallest garden on it until you have worked out what the owner was trying to do. Nothing in the tents will hold you that long.