5 DuPage Downtowns Worth Exploring Before Summer Ends
Summer may be winding down, but some of the best reasons to explore Chicago’s western suburbs are still ahead.
Late August is a particularly good time to visit DuPage County’s downtown districts. Farmers markets are still running, outdoor art remains on display, festivals are filling local parks, and patios are still busy before fall schedules take over.
And these are not interchangeable suburban Main Streets. Naperville, Wheaton, Glen Ellyn, Elmhurst, and Downers Grove each offer a noticeably different way to spend a summer afternoon or evening.
If you have a few weekends left before the season changes, these five downtowns deserve a spot on the list.
1. Downtown Naperville
If you want the downtown with the most to fill an entire day, Naperville is the obvious place to start.
The Naperville Riverwalk gives downtown something few suburban business districts can match: 1.75 miles of brick paths along the West Branch of the DuPage River, with covered bridges, fountains, public art, landscaped gathering areas, and easy connections back into the restaurant and shopping district.
Late summer also gives visitors one last chance to catch Downtown Naperville’s Summer Painted Sculptures. This year’s installation features 24 painted dog sculptures and one cat placed around downtown, and they remain on display through September 1.
Then comes Naperville’s unofficial goodbye to summer. The Naperville Jaycees’ Last Fling returns September 4 through 7, bringing live music, food, carnival rides, family activities, a business expo, and the Labor Day Parade to the downtown and Riverwalk area.
That mix is what makes Naperville work so well for a spontaneous summer day. You can walk the Riverwalk in the morning, stop downtown for lunch and shopping, and stay into the evening without needing to move the car.
Naperville’s downtown is also a major reason the suburb continues to receive national attention. Earlier this year, Naperville was named the No. 1 Best City to Live in America, with its walkability, community amenities, schools, and overall quality of life contributing to its appeal.
2. Downtown Glen Ellyn
Glen Ellyn is probably the downtown to visit right now if you want an actual late-summer event weekend.
From August 20 through 23, the Glen Ellyn Chamber Carnival takes over the Crescent/Glenwood lot downtown with rides, games, concessions, and a classic end-of-summer carnival atmosphere.
At the same time, one of the village’s biggest cultural weekends happens just minutes away.
The 57th Annual Festival of the Arts runs August 22 and 23 from 10 a.m. to 5 p.m. at Lake Ellyn Park, bringing together dozens of artists, live music, food, beer, children’s activities, and the village’s ongoing Summer of the Monarch programming.
Lake Ellyn itself is part of the reason this stop feels different from the other downtowns on this list. The 28.7-acre park sits close enough to downtown that it is easy to combine the festival with restaurants, shops, and a walk through Glen Ellyn’s compact business district.
Downtown Glen Ellyn is also directly served by the Metra Union Pacific West Line, making it one of the easier DuPage day trips if you would rather leave the car behind.
There is also a real estate reason buyers keep gravitating toward the area. Glen Ellyn combines an established downtown with older residential architecture, parks, train access, and highly sought-after neighborhoods. Our latest Glen Ellyn housing market update shows how that lifestyle appeal continues to support strong housing demand.
3. Downtown Wheaton
Wheaton is at its best on a Saturday morning.
The Wheaton French Market continues on August 22 and August 29 from 8 a.m. to 2 p.m., bringing fresh produce, flowers, baked goods, specialty foods, crafts, jewelry, and rotating vendors to the pavilion near Main Street and Liberty Drive.
On August 22, there is an added reason to stay downtown. The Wheaton Concours Car Show runs from 10 a.m. to 2 p.m. at Memorial Park, so visitors can move almost seamlessly from the market to the car show and then into the surrounding restaurant and retail district.
If you cannot make that weekend, Wheaton still has another strong end-of-August option. Shakespeare in the Park is scheduled at Memorial Park on August 27, 28, and 29 at 7 p.m.
The downtown itself has more depth than many first-time visitors expect. The Downtown Wheaton Association counts more than 200 locally owned businesses and over 50 restaurants within the district, alongside boutiques, arts and cultural destinations, and frequent community events.
Wheaton is less about one headline attraction and more about how easily everything connects. The French Market, Metra station, Memorial Park, restaurants, boutiques, and Illinois Prairie Path are all close enough to make downtown feel genuinely walkable.
4. Downtown Elmhurst
For something more visual, head to Elmhurst before the umbrellas come down.
The Umbrella Sky Project is still suspended above sections of downtown through September 30, transforming ordinary streets into a canopy of color. Elmhurst is only the sixth U.S. city to host the internationally exhibited installation, making this more than typical seasonal downtown decoration.
Summer is also one of the easiest times to explore more of the city without constantly searching for parking. The Explore Elmhurst Express Trolley continues operating Fridays and Saturdays through September 19, providing free hop-on, hop-off transportation between downtown and other Elmhurst destinations.
On Sundays, the Elmhurst French Market continues through September 27 from 9 a.m. to 2 p.m., giving visitors another reason to combine brunch, shopping, and a walk through downtown.
That makes Elmhurst particularly good for someone who wants a less event-dependent day. You do not have to arrive during a specific two-hour festival window to have something to see.
Downtown also plays a large role in Elmhurst’s appeal as a place to live. Our guide to living in Elmhurst looks more closely at its walkability, Metra access, restaurants, housing, and proximity to Chicago.
5. Downtown Downers Grove
Downers Grove is the pick when you want a downtown that still feels distinctly local.
Start on Saturday morning at the Downtown Downers Grove Market, held near the Main Street train station. The market continues through October 17, including upcoming dates on August 22 and August 29, with food, local vendors, and live music creating a busy morning around the station.
From there, Main Street gives you plenty of reasons not to leave immediately. Downtown Downers Grove has maintained a mix of independent shops, restaurants, coffee spots, entertainment, and community gathering places that makes it feel less like a planned shopping district and more like an established town center.
One of its defining landmarks is the historic Tivoli Theatre, a fully restored downtown movie house that still pairs modern projection with the atmosphere of a classic suburban theater. On Saturday evenings, the main auditorium even features its Wurlitzer pipe organ before the first show.
That combination of market, Metra access, historic architecture, restaurants, and local businesses makes Downers Grove a particularly easy place to spend a slower summer Saturday without needing a major festival as the reason to go.
Which DuPage Downtown Should You Visit First?
That depends on the kind of day you want.
Choose Naperville when you want a full day built around the Riverwalk, shopping, dining, and late-summer activity. Head to Glen Ellyn this weekend if art, a carnival, and Lake Ellyn sound better. Pick Wheaton for the French Market, Memorial Park, and a compact walkable downtown.
Elmhurst is the most photogenic choice while Umbrella Sky is still up, while Downers Grove works best for a relaxed Saturday built around the market, Main Street, and the Tivoli.
What they have in common is that none requires a trip into Chicago to deliver a genuinely walkable day of food, shopping, events, and local character.
For even more communities to explore, see our guide to the best downtowns in Chicago’s Western Suburbs.
Thinking About Making DuPage County Home?
Visiting a downtown is also one of the fastest ways to understand what living in a suburb actually feels like. Walk from the train station, see where people gather on a Saturday, explore the surrounding residential streets, and notice how easily restaurants, parks, shops, and everyday errands fit together.
The Cory Tanzer Group at Option Premier helps buyers and sellers throughout DuPage County and Chicago’s Western Suburbs, including Naperville, Wheaton, Glen Ellyn, Elmhurst, Downers Grove, and surrounding communities.
If one of these downtowns feels like somewhere you could see yourself living, we can help you compare neighborhoods, commute options, current inventory, and the local housing market before deciding where to focus your search.
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