Downtown Naperville has two weeks left with one of its longest-running wine rooms. Sixty-Four Wine Bar & Kitchen at 123 Water Street serves its last guests on Wednesday, Nov. 25, and its Reserve Room closes with it. In September, Lennon's on West Jefferson closed about a year after opening.
The businesses opening in the same few blocks are a different kind of place. Downtown has gained churros, açaí bowls and gyros, and 15 W. Jefferson is the address for a Mexican restaurant planned around breakfast, lunch and dinner. Where the departing venues asked guests to settle in for the night, most of the new ones are built for a single stop, which turns an evening downtown into a short walk between several counters.
Two Closings at 16 W. Jefferson
The clearest example is a single storefront. The Daily Herald reported that Lennon's opened at 16 W. Jefferson Ave. in August 2025 as a mixed dining and entertainment concept. Owner Jeremy Stolberg had described it as a place where guests would "come and stay." The restaurant announced its closing on social media in September and wrote:
"This is not the goodbye we hoped to have, but we are deeply thankful for the time we were given and for every person who was part of the Lennon's story."
The same report said the space had been through this before. AltaVida, a Latin-inspired entertainment complex with a casual Spanish cafe, operated there before Lennon's and also closed in less than a year. Downtown Naperville Alliance Executive Director Dawn Portner told the paper that Lennon's gave no reason for closing. Twice in a row, a concept built around staying for the whole night lasted about a year or less at this address.
Across the Street, Smaller Formats
Two doors east, at 8 W. Jefferson Ave., Lola's Handcrafted Churros opened in late September. It sells handmade churros, churro loops and churro sundaes. Owner Mayra Serna founded the business with her sisters. The Daily Herald noted that Naperville is Lola's third location. A churro sundae takes the length of a stroll. The storefront is built to be one stop on a longer evening.
Directly across from the former Lennon's space, 15 W. Jefferson Ave. is the address for Jose and Ivonne Oliver's Cantina Taco Grill. Jose Oliver also runs Taco Grill and Salsa Bar in Westmont. He told the Daily Herald he had hoped to open on Sept. 15 but moved the date because of unforeseen issues. NCTV17 listed Oct. 29 as the planned opening.
Cantina is the full-service restaurant in this group, and it is planned around the clock more than around late nights. The plan calls for breakfast, lunch and dinner seven days a week. Chicago Food Magazine described a brunch menu with shrimp-and-poblano omelets and chilaquiles, and later meals of tacos, seafood, steaks and house-made margaritas. The Daily Herald's preview also mentioned bone marrow and pork belly tacos and salmon with mole sauce. Serving three meals a day means the room fills at several points in the day instead of relying on the late evening.
The Fall Downtown Roster, Block by Block
Sorted by street, the changes all fall within a short walk of each other.
| Business | Address | What it serves | Status on Nov. 12 |
|---|---|---|---|
| Lola's Handcrafted Churros | 8 W. Jefferson Ave. | Churros, churro loops, sundaes | Open since late September |
| Cantina Taco Grill | 15 W. Jefferson Ave. | Modern Mexican, three meals a day | Announced for fall 2026 |
| Former Lennon's | 16 W. Jefferson Ave. | Dining and entertainment | Closed in September |
| State & Liberty Clothing Co. | 144 W. Jefferson Ave. | Men's athletic-fit clothing | Targeting mid- to late November |
| I Heart Gyro | 22 E. Chicago Ave. | Greek and Mediterranean | Open |
| Deep Purpl | 120 Water St., Suite 101 | Brazilian açaí bowls | Open |
| Sixty-Four Wine Bar & Kitchen and Reserve Room | 123 Water St., Suite 105A | Wine bar and kitchen | Last day of service Nov. 25 |
| SEE Eyewear | 214 S. Main St. | Prescription glasses and sunglasses | Slated for November |
The Chicago Avenue and Water Street openings fit the same pattern. I Heart Gyro took over a space at 22 E. Chicago Ave. that another gyro shop had occupied. Founder Khalil Faykov opened the first I Heart Gyro in Vancouver, Washington, about 10 years ago and describes it as a fast-casual restaurant. "Hopefully this will become the spot for gyros in the area," he told the Daily Herald. Naper Today reported in mid-October that Deep Purpl, a Brazilian açaí bowl cafe, had opened at 120 Water St. Portner also listed Lizzano Focacceria & Spritzeria and Slyce of NY, a New York-style pizza concept, among the businesses coming to downtown. Both are smaller-format food concepts.
Sixty-Four's Last Two Weeks
Sixty-Four is the exception on this list. It is leaving after a decade, and the shorter-lived concepts set that run in context. Patch reported that the owners announced the closing after 10 years in Naperville, saying it was "time to move on with other opportunities."
If you are a regular, the details are practical:
- Last day of service: Wednesday, Nov. 25, the day before Thanksgiving.
- Gift cards and platinum cards: The owners ask holders to use them before the closing. Refunds after the closing can be arranged by calling 630-780-6464.
- Event bookings: Anyone who reserved the space for an event can get a deposit refund through the same number.
- The Reserve Room: It closes along with the main wine bar and kitchen.
That leaves two weekends for a final visit, and the final weeknight falls on the busiest travel evening of the holiday week.
More Visits, Shorter Stays
Downtown is not losing visitors. On Oct. 7, at the Naperville Area Chamber of Commerce's State of the Naperville Commercial Real Estate event, Naperville Development Partnership President Monica Conners said downtown economic growth tracked through the city's Placer AI software was up 15% year over year. She said Block 59 was up 125% over the same period. According to Naper Today, she also said the city now has more than 400 restaurants.
With traffic up and long-format venues closing, the visits downtown is gaining look different from the ones it is losing. A downtown evening this winter is more likely to run from a gyro on Chicago Avenue to an açaí bowl on Water Street, and then to churros on Jefferson.
Here is a short walking route that covers this fall's changes before Sixty-Four closes:
- Start at Sixty-Four at 123 Water St. for a last glass in the room on or before Nov. 25.
- Walk next door to Deep Purpl at 120 Water St. for something lighter.
- Cross toward I Heart Gyro at 22 E. Chicago Ave.
- End on West Jefferson at Lola's Handcrafted Churros, number 8, across from the Olivers' Cantina Taco Grill at number 15.
If State & Liberty opens on its mid- to late-November target, 144 W. Jefferson adds a retail stop at the far end of the same street.
Living within walking distance of Jefferson Avenue and Water Street means living with this kind of turnover from season to season. If you want to know how it affects owning a home in walking range of downtown, Jill Clark will talk it through with you over a quiet conversation. Request a Private Consultation.
