Naperville This August: One Owner, Two Restaurant Districts, and the Last Free Weekend of Summer

"We provide a second destination for folks to come and really have a great dining and entertainment experience." That line came from Rich Dippolito, the developer behind the $53 million overhaul of Westridge Court into what's now called Block 59, and he wasn't talking about downtown. He was talking about Route 59, three miles west of the Riverwalk, where a shopping center that opened in 1990 is turning into Naperville's second dining district. Meanwhile, back on Washington Street, one restaurant group has quietly picked up four of downtown's best addresses. Two different bets on the same summer, and if you've eaten out in Naperville even twice this year, you've probably tasted both without realizing they were connected.

The Address Downtown Keeps Handing to the Same Person

Will Cullen opened his first Naperville restaurant, Empire Burgers + Brew at 48 W. Chicago Ave., back in 2016. A decade later, his company, Empire Restaurant Group, controls a stretch of downtown real estate tight enough to walk in ten minutes:

• Empire Burgers + Brew, 48 W. Chicago Ave.
• Northcott Liquorette, 40 W. Chicago Ave., a Prohibition-styled speakeasy concept with absinthe fountains
• The George, 245 S. Washington St., an American tavern that opened this year with menu items named for real Naperville figures, including a burger stamped table-side with a replica of former mayor George Pradel's police badge
• The Belmont American Steakhouse, 35 S. Washington St., Cullen's sixth concept, now open in the space Catch 35 occupied for 21 years before closing in June 2025

That last one is worth sitting with. Catch 35 ran for two decades as one of downtown's anchor seafood rooms. When it closed, the space didn't go to a new independent owner rolling the dice on a concept. It went to someone who already had three other properties within a four-block radius. If you've noticed The George's dining rooms filling up fast on weeknights, or that Northcott's speakeasy vibe and The Belmont's steakhouse menu feel like they were built by people who talk to each other, that's because they were.

Three Miles West, a Different Kind of Downtown

Block 59 exists because of a gap Dippolito's team identified: residents on Naperville's west side were driving up to 20 miles for restaurants they could otherwise get closer to home. The fix wasn't another independent concept. It was recognizable national brands, clustered fast.

Cheesecake Factory and First Watch opened first, followed by Shake Shack, Stan's Donuts & Coffee, Velvet Taco, Yard House, Crisp & Green, and Piccolo Buco, a Cooper's Hawk-backed pizza concept. CAVA is still coming. So is Ruth's Chris Steak House, expected sometime this year.

So downtown and Block 59 aren't competing for the same dinner reservation anymore. Downtown is doubling down on ownership concentration and local history. Block 59 is betting on brand recognition and proximity. If you live on the west side and used to default to downtown for every dinner out, this is the year that stopped being the only option.

The Weekend That Just Changed the Shape of the Calendar

This past Sunday, Naperville Neighborly Days returned to downtown for the first time in two years. The block party, formerly known as Old Naperville Day, had been on hold because of the Washington Street Bridge repairs that tied up the same stretch of downtown the event usually occupies. With the bridge work finished, the city brought it back on August 9, an 11 a.m. to 7 p.m. run through the heart of downtown.

Tomorrow night closes out River Sounds, the free Tuesday concert series that's run at Jaycees WiFi Park since July 7. It's a small, specific kind of programming: musicians play from the lawn until around 8 p.m., then the show shifts to a floating stage just west of the covered bridge, so the music carries across the DuPage River instead of just across the grass. Tomorrow is the last one this season.

Between the two, this is the week the free, walk-up-anytime version of Naperville's summer calendar starts to thin out, right as the ticketed, plan-ahead events take over.

What's Free, What's Ticketed, and What's Left

The free Friday movie series opened July 31 at Rotary Hill and already played Goat on Aug. 7, but Shrek on the 21st and the Mario movie on the 28th are both still ahead, with bingo starting at 7:30 p.m. and the film at 8:30. If you've never gone to a Naper Nights show, know that it's a paid lawn concert at Naper Settlement, not one of the town's free series.

Last Fling Is Coming

The season's biggest event is still ahead. Naperville's Last Fling runs Labor Day weekend, Sept. 4 through 7, with live music, a carnival, and festival food filling downtown before it wraps with the Labor Day Parade on the final day. Locals who've lived through a few of these know the pattern by now: the back half of August turns kinder, warm days and cooler evenings, and the kind of light on the Riverwalk that "makes the Riverwalk look staged." That stretch is exactly why so many people refuse to book anything over the holiday weekend itself. The town saves its biggest party for last, and it's easier to enjoy once you're not also stuck driving back from somewhere else.

Between now and then, downtown's summer sculpture display is still up along the Riverwalk if you haven't walked the full route yet, and both farmers markets are hitting peak sweet corn and tomato season.

The Short Version

Two dining districts are pulling in different directions this summer, and one operator now holds enough of downtown's real estate to make that trend visible from a single walk down Washington Street. Layer that onto a calendar that just lost its free Tuesday-night concerts and just got a two-year-absent block party back, and August in Naperville looks less like a slow wind-down and more like the town rearranging its own habits in real time.

If you're the kind of resident who tracks these shifts because you love this place, you already know that the same instincts that tell you where to eat downtown this month are the ones worth having when you're finally ready to talk about buying or selling here. Alejandro Trujillo and the team at RE/MAX NEXT work Naperville block by block, the same way they'd tell you where to find parking for Last Fling. Whenever that day comes, reach out for a home valuation, or just to talk through what your corner of downtown is actually worth these days.