Downtown Oswego's Old Restaurant Spaces Are Filling Back Up, Mostly After the Holidays

The former Danelli's on Washington Street, the old Dairy Barn on Main and the former Freddie's Off The Chain on Madison are all getting new restaurants, and so is the long-vacant building at 5 S. Madison. That's one of the largest groups of downtown Oswego storefronts to change hands at the same time in years. Village Hall has approved incentives for most of these projects, and for the buildings around them, over the past six months.

Nearly every one of them is aiming to open around or after the Dec. 4 Christmas Walk, the biggest night on the downtown calendar. The new places should arrive close together around the turn of the year, so for this holiday season downtown still depends on the businesses that are already open.

The addresses Oswego already knows by name

Many people in Oswego will still call these buildings by their old names for a while. Here's what is moving into each one, based on the Village's downtown business page and local reporting from this year.

The Danelli's building has the longest history here. Danelli's Italian Restaurant & Pizzeria served from that spot starting in 1985 and closed in December 2024 when its owners retired, Shaw Local reported. Hell's BBQ is moving in from its first brick-and-mortar location at 1019 Station Drive. Owner Keith Richards first announced this summer that the restaurant would close, then changed course and announced the move downtown, according to Patch. Until the new location opens, the Hell's BBQ food truck has been parking at 111 S. Lake St. in Montgomery.

The Main Street building has gone through two closures. Dairy Hut closed in August 2019, and the Dairy Barn that replaced it closed in 2022, Shaw Local reported in July. Wholey Granoly plans to serve breakfast and lunch there and is proposing to enclose the building's existing outdoor patio.

On Madison, DillaDawgs started as an Aurora food truck about a year and a half ago, selling hot dogs and quesadillas. Its announcement for the former Freddie's space mentioned loaded fries, mac and cheese "and yes… there will be a BAR!" as Patch reported. A few doors down, Billy Bricks is doing a substantial buildout of 5 S. Madison for wood-fired pizza, pasta, sandwiches, salads and ice cream.

Village Hall has bet on buildings, too

Several of the incentives pay out only once a business opens or starts making sales.

The $40,000 award for Wholey Granoly depended on the restaurant signing a lease and opening within six months. Ellwood Steak & Fish House gets its $40,000 grant when it opens. The rest of its package, up to $300,000, comes as sales-tax rebates spread over as many as 10 years, so the Village pays only as the restaurant brings in sales. Hell's BBQ already received a $30,000 Village loan in May 2023 for its Oswego Junction restaurant. A Village official told the board the business is still current on those payments, and the new $40,000 award will help pay for about $100,000 in improvements on Washington Street.

The Village's most recent awards for empty buildings follow a different pattern. On Sept. 15, the Village Board voted 5-0 to approve $32,831 for 8 W. Washington St. and $30,327 for 12 W. Washington St., according to the official minutes. Neither building has a tenant. At 8 W. Washington, the planned work includes new siding, gutters, soffits, downspouts, windows and doors, plus paving the gravel parking lot. Board members discussed retail, a restaurant or a medical office as possible uses. At 12 W. Washington, the second-floor residence stays, and the work includes new siding and a larger entrance deck so the first floor can attract a commercial tenant.

With those two awards, the Village has approved incentives to help get buildings ready to lease before any business has signed on. That means more announcements on Washington Street are likely to follow this year's group.

What's already open on Main Street

Until the new restaurants open, downtown's evenings depend on the businesses already operating. The newest is Bay 54, a cocktail lounge at 57 Main St. that opened July 24, according to Patch. Its owners, Dan and Aimee Thomas, are a Plainfield couple, Shaw Local reported. Nash Vegas Saloon, a restaurant and live-music venue, has been open since July 2024 in a 6,200-square-foot former brewery space.

For daytime shopping, American-Male, a men's clothing store, opened at 27 Main St. in June 2025, and Paws on Main, an independent pet supply store, opened in March 2024. These are the storefronts that will host the open houses, crawls and walks on the calendar below.

The season, with the openings lined up against it

Here are the downtown dates from the Downtown Oswego Association and the Oswegoland Park District, along with each new business's stated target. Targets are shown as the businesses or the Village described them, not as confirmed dates.

1. Saturday, Oct. 24, 10 a.m. to 2 p.m. Downtown trick-or-treating.
2. Nov. 5 to 8. Holiday open houses at downtown shops.
3. Saturday, Nov. 7, 10 a.m. to 2 p.m. Coffee/Cocoa Crawl.
4. Sunday, Nov. 8. The Park District's Gobbler Hobbler 10K and Mashed Potato Mile.
5. Early to mid-November. Trader Joe's is expected to open at 1930 U.S. Route 34, near Kendall Point Drive.
6. Nov. 20 and 21. The Park District's Fall Play.
7. Nov. 27 and 28. Shop Small weekend downtown.
8. Friday, Dec. 4, 4:30 to 8:30 p.m. The Village Christmas Walk, with a parade of lighted emergency vehicles down Main Street.
9. Saturday, Dec. 5, 10 a.m. to 2 p.m. Cookie Walk.
10. Dec. 10 to 12. The Park District's Holiday Express.
11. Saturday, Dec. 12, 9 a.m. Jingle Bell Jog downtown.
12. Dec. 16 to 19. "A Christmas Carol" radio play from the Park District.
13. End of fall. Wholey Granoly's target at 121 S. Main St.
14. By year-end. The targets for Hell's BBQ on Washington Street, Billy Bricks on Madison and phase one of Harrison Street Square.
15. End of 2026 or early 2027. Ellwood Steak & Fish House at 180 W. Washington St.

Trader Joe's is the only opening on that list that lands well before the holiday events. It's out on Route 34 near Delta Sonic, not downtown. Bistro Manila is also coming to the Route 71 side of town, moving from Naperville into 4542 Route 71, the former Asadoras Argentinas Burgers. It said it would announce an opening date later, Patch reported.

Plans can still shift. Ellwood's timeline is one example. When the Village Board approved its incentives in June, Shaw Local reported that the restaurant hoped to open by October. The Village's page now says end of 2026 or early 2027, and the restaurant was still in plan review when that page was updated. Remodeling an old building tends to take longer than expected.

Harrison Street Square runs into 2027

The biggest change on the list is also the one that will take longest. Harrison Street Square at 174 S. Harrison St. is turning a former industrial building into a retail center. Phase one, the interior conversion, is expected to finish by the end of 2026. After that, phase two moves outside the building, adding small pop-up shops and community open space. TermiNader Fitness, a planned boutique training studio that received a $34,705 Village award in May, is the only committed tenant so far.

By next year's Christmas Walk, Washington Street could have Hell's BBQ, Ellwood, and new tenants in the two refurbished buildings at 8 and 12 W. Washington. Madison could have DillaDawgs and Billy Bricks on the same block. Harrison Street could have its first outdoor space. This year's walk will use the downtown that's already open, with paper still covering several of the windows nearby.

If you're watching these storefronts change and wondering what it means for the homes a few blocks away, Marzena Castillo follows downtown Oswego closely. Schedule your free consultation, and we can go over what's happening near your street.