Walk Jackson Avenue on the morning of September 19 and you will see booths going up before most people are on their second cup of coffee. This is not a new sight. The Riverwalk Fine Art Fair has closed this stretch of downtown every September since 1985, and this year's edition, the 41st, runs September 19 and 20 from 10 a.m. to 5 p.m., with more than 100 juried artists setting up along the brick paths between Main and Eagle Streets.
What is different this year is everything happening around it, and one thing that finally stopped happening to it.
Three Events, One Footprint
Locals who have lived through a few Septembers know this month gets crowded, but 2026 stacks its calendar in an unusual way. West Suburban Irish brings Irish Fest to Central Park on September 18 and 19. A summer food truck festival lands at Naper Settlement on September 19, the same day. And the Riverwalk Fine Art Fair opens that Saturday and runs through Sunday. Three separate organizers, three separate venues, one overlapping weekend.
| Event | Dates | Location | Hours |
|---|---|---|---|
| Irish Fest | Sept 18 to 19 | Central Park | Varies by day |
| Summer Food Truck Festival | Sept 19 | Naper Settlement | Daytime |
| Riverwalk Fine Art Fair | Sept 19 to 20 | Jackson Ave and the Riverwalk | 10 a.m. to 5 p.m. |
None of these three require a ticket to browse. All three sit within walking distance of each other in the compact downtown grid, which means a single Saturday could realistically include Celtic bands in Central Park, a food truck lunch at Naper Settlement, and an evening stroll past oil paintings and blown glass on Jackson Avenue. Locals have started calling this stretch the unofficial finale of festival season, arriving two weeks after Last Fling closes out Labor Day weekend with its own parade and carnival.
The practical piece worth remembering: downtown's public parking garages do not charge, on this weekend or any other. The Municipal Center Parking Deck at 400 S. Eagle St. sits closest to the western end of the Riverwalk, and the Central Parking Facility at 75 E. Chicago Ave. puts you near Fredenhagen Park and a run of dinner options once the art booths close for the day. Park once, walk the rest.
The Fence That's Finally Gone
Anyone who attended last September's fair, the 40th, may remember a section of the Riverwalk near the Dandelion Fountain and the Free Speech Pavilion looking a little unfinished. That was the Eagle Street Gateway project, a piece of the city's long-range Riverwalk 2031 Master Plan that had been on the books since around 2010 before construction actually started.
The city broke ground on the project in March 2025, with Naperville's Director of Transportation, Engineering, and Development, Bill Novack, describing the scope at the time:
"It will have stairs, ramps that get down to the lower walkway, and a ton of great landscaping."
The target completion was Labor Day weekend 2025. That date has now passed by a full year, which means this fair should be the first in several editions where fairgoers can walk that section of Jackson Avenue without a construction fence rerouting foot traffic around it. The project added two grand staircases, a wheelchair accessible ramp, and a second point of street level access near the Landforms sculpture, work that Congressman Bill Foster helped fund with $900,000 in federal community project dollars. The bigger Riverwalk 2031 plan behind it is aiming at two milestones at once: the Riverwalk's 50th anniversary and Naperville's 200th, both landing in 2031.
For a fair that depends on foot traffic moving smoothly between booths, food vendors, and the Riverwalk's fountains and bridges, a fully open path changes the shape of the day. Fewer bottlenecks near the Eagle Street corner means the crowd that used to pool up there can now keep moving toward the Free Speech Pavilion, where the DuPage Symphony Orchestra ensembles have performed in past years, and on toward the Water Street district.
Where to Refuel: The George's History Lesson
If the fair puts you in the mood for dinner within walking distance, downtown added a genuinely new option this year. The George opened at 245 S. Washington St., an upscale American tavern from owners Dave Miller and Will Cullen built around four distinct seating zones and a covered pergola patio. What sets it apart from a typical new opening is the research behind the name. Miller and Cullen worked with the Naperville Historical Society to build the concept around four real historical figures who all happened to share the name George, including George Pradel, the city's mayor for 20 years, and George Knoch, the namesake behind Knoch Park.
The signature George Dip, a prime rib French dip served with herbed au jus, sits alongside the Badge 13 Burger, a dry aged double patty stamped at the table with a cast iron replica of Pradel's original police badge from his years as Naperville's 13th officer. It is the kind of detail that turns a restaurant opening into a small local history lesson, and it gives fair weekend visitors a reason to treat downtown as a full evening rather than a two hour walkthrough.
The Other Dining Story, a Few Miles South
Downtown is not the only place Naperville's food scene has changed this year. A few miles south at Route 59 and Aurora Avenue, the $53 million redevelopment of the former Westridge Court shopping center, now branded Block 59, has been filling in fast. CAVA opened there on January 12, 2026, bringing Mediterranean bowls and pitas to a corridor that already includes Yard House, Piccolo Buco, Shake Shack, First Watch, and an 8,700 square foot Cheesecake Factory.
The contrast is worth noticing. Downtown's newest opening leans on 19th and 20th century Naperville names and a Historical Society partnership. Block 59's newest additions are national fast-casual and full-service brands arriving at a car-oriented shopping corridor built for a different kind of visit, quicker, driven to, parked directly in front of. Both are genuine growth. Neither replaces the other. Together they say something about where Naperville's dining identity is actually headed: outward as well as inward, with downtown doubling down on its own story while Route 59 imports the brands that suburban Chicago diners already know from Bolingbrook or Willowbrook.
How to Actually Spend the Weekend
If you are deciding how to split September 19 and 20, the logical version looks something like this. Morning at Irish Fest in Central Park on Friday or Saturday. Lunch from a food truck at Naper Settlement Saturday afternoon. Then walk the Riverwalk Fine Art Fair booths along Jackson Avenue as the light softens toward evening, when the crowds thin and the DuPage Symphony's ambient sets carry further across the water. Dinner at The George if you want the newest downtown option, or a patio table in the Water Street district if you'd rather stay riverside.
Sunday belongs to the fair alone, since Irish Fest and the food truck festival wrap Saturday. That makes Sunday the quieter of the two days for browsing art, a detail worth knowing if crowds aren't your favorite part of a festival weekend.
None of this requires a car once you've found a garage spot. That has been true of downtown Naperville for years, and it is one of the few things about this September that has not changed.
If you're the kind of resident who tracks these small shifts in your own neighborhood, downtown's newest restaurant, a finished construction project, a shopping center quietly filling back up, you already understand what makes a place worth staying in. The Kelly Schmidt Group spends the same kind of attention on Fox Valley real estate. If you're ever curious what any of that local momentum means for your own home's value, reach out anytime for a Free Home Valuation.
