At U.S. Route 34 and Kendall Point Drive, next to Delta Sonic, a new grocery store is close to opening. Oswego Economic Development Director Kevin Leighty told Shaw Local that Trader Joe's at 1930 U.S. Route 34 is expected to open in early to mid-November. The interior buildout was due to finish this month, and then the shelves get stocked. Three miles of village road away, downtown Oswego begins its own season. The Oswego Downtown Association's Holiday Open Houses run November 5 through 8.
Both seasons start in the same few weeks, but they work differently. On Route 34 you show up whenever you like. Downtown runs on short windows, most of them on Saturday mornings, and a few deadlines come weeks before the events they unlock. Plan around those windows and deadlines and the season is easy. Miss them and you'll be reading about the Cookie Walk afterward.
The Route 34 track: one opening, more on the way
The Trader Joe's opening window is a projection, not a confirmed grand-opening date, so plan on "sometime in the first half of November." The paperwork is mostly done. Village trustees approved a packaged-liquor license for the store at the August 18 Village Board meeting. The company is also building a store at 2741 Plainfield Road in Joliet's Joliet Commons, in the former JoAnn space, and that one is expected by early December.
The corridor is still filling in. The Village's Route 34 development page lists Dutch Bros near Ogden Falls Boulevard for late 2026 or early 2027 and HomeGoods at Prairie Market East for early 2027. None of that changes this December. It does mean the east side of town will run errands on a different map next year.
Ogden Point, the Oswegoland Park District's new center at 201 Ogden Falls Blvd., sits off the same stretch. It opened September 8 for athletics, fitness classes and gym rentals. The four-lane pool and aquatics programs are slated for Winter 2027, so for the rest of 2026 the building is gym and fitness space only. For a cold Saturday afternoon after a downtown morning, it's a new indoor option that didn't exist last December.
The downtown track: a season built in four-hour blocks
Nearly every downtown event is a single morning or midday block, and almost all of them land on a weekend.
| Date | Event | Window | Host |
|---|---|---|---|
| Sat., Oct. 24 | Downtown Trick or Treat | 10 a.m.–2 p.m. | Oswego Downtown Association |
| Thu.–Sun., Nov. 5–8 | Holiday Open Houses | Store hours | Oswego Downtown Association |
| Sat., Nov. 7 | Coffee/Cocoa Crawl | 10 a.m.–2 p.m. | Oswego Downtown Association |
| Sun., Nov. 8 | Gobbler Hobbler 10K & Mashed Potato Mile | See Park District | Oswegoland Park District |
| Fri.–Sat., Nov. 27–28 | Black Friday / Shop Small Saturday | Store hours | Oswego Downtown Association |
| Fri., Dec. 4 | Christmas Walk | 4:30–8:30 p.m. | Village of Oswego |
| Sat., Dec. 5 | Cookie Walk | 10 a.m.–2 p.m. | Oswego Downtown Association |
| Sat., Dec. 5 | Oswego Country Market Holiday Market | 9 a.m.–noon | Oswegoland Park District |
| Sat., Dec. 12 | Jingle Bell Jog | 9 a.m. | Oswego Downtown Association |
The first block is this Saturday. Downtown Trick or Treat runs October 24 from 10 a.m. to 2 p.m. with no registration, and maps of participating stores were scheduled for release October 21. The Christmas Walk is the one evening event in the lineup, and it's the one the rest of the calendar builds toward.
The dates that come before the dates
Two deadlines on this calendar arrive well ahead of their events.
The first is Tuesday, November 24, at 10 a.m. That's when Cookie Walk tins go on sale, online only. The Downtown Association is clear that you have to buy this year's tin to take part in the December 5 walk. The tin price and collection details hadn't been posted as of mid-October, so the association's events page and Facebook are where the purchase link will show up.
The second is December 1. That's the last day for refunds on Oswego Holiday Express, the Park District's shuttle-based event at South Point. Everyone who comes has to be registered, infants included, and children under two get $10 off. Shuttles leave every 20 minutes, and accessible shuttles run on Friday evening. The Park District's October highlights list Holiday Express as December 10–12, but the registration system shows sessions Friday through Sunday, December 11–13. Those dates line up with the calendar, so book from the registration listing.
December 4 through 6 is the weekend to plan first
Most of the season comes down to one three-day stretch. In order:
- Friday, December 4, 4:30–8:30 p.m. The Village's free Christmas Walk goes on rain or shine. It has local choirs, Santa's reindeer, live ice sculpting, an inflatable sled hill, the annual tree lighting performance, and Santa's "North Pole home away from home" for kids with wish lists. Later in the evening, the Oswego Fire Protection District leads its illuminated emergency vehicle parade down Main Street, with decorated trucks, cars and favorite characters. Downtown stores open their doors for browsing. The Village says more 2026 details are coming, and it posts updates on its Facebook page.
- Saturday, December 5, from 9 a.m. The Oswego Country Market Holiday Market runs 9 a.m. to noon at the Little White School Museum. The Cookie Walk starts at 10 a.m. and runs until 2 p.m. The two overlap for two hours, so you can do both in one morning if you already bought your tin in November.
- Sunday, December 6. The Park District hosts Family Gingerbread House Decorating.
The next weekend fills up too. Holiday Express runs December 11–13, and the Jingle Bell Jog steps off Saturday, December 12, at 9 a.m. The jog has no timing and no awards. Every runner gets a long-sleeve tech shirt and jingle bells, and Santa, cocoa and cookies wait at the finish. The Park District's Date Night Drop-Off is on the calendar that same Saturday.
After that, the Park District schedule moves indoors and gets quieter. It lists Santa on the Line on December 15, the A Christmas Carol radio play December 16–19, and Happy Noon Year on December 31. Gingerbread Drink & Decorate sessions for adults run December 1, 3 or 9.
The downtown watch list
The storefronts on these walks are changing, too. Several downtown restaurants are in the works, and none has a confirmed opening date yet. Don't plan the Christmas Walk around any of them. Just watch for them.
- Hell's BBQ is moving to 228 E. Washington St. The Village approved a $40,000 incentive for the space, and the owner hopes to open by year-end, with a patio planned as a later phase, Shaw Local reported.
- Wholey Granoly is a breakfast spot going into the former Dairy Barn space at 121 S. Main St., according to Shaw Local. The Village's downtown page targets the end of fall.
- Billy Bricks is coming to 5 S. Madison St. The Village lists it for the end of 2026, and the restaurant has an announcement list for its grand opening.
- DillaDawgs is the Aurora food truck heading into the former Freddie's Off The Chain space at 11 S. Madison St., Patch reported. Its website still says "coming soon."
- Ellwood Steak & Fish House is planned for 180 W. Washington St. The Village's downtown page puts it at the end of 2026 or early 2027.
- Bistro Manila is a Filipino counter-service restaurant relocating from Naperville. It's taking over 4542 Route 71, the former Asadoras Argentinas Burgers, with no opening date announced, according to Patch.
At 174 S. Harrison St., the Village expects the first retail phase of Harrison Street Square, with TermiNader Fitness as a committed tenant, to finish by the end of 2026. An outdoor second phase follows. If you want the backstory on how downtown storefronts have been filling, our earlier piece on Oswego's storefront loan fund covers it, and our Oswego neighborhood guide has the wider picture.
Trader Joe's is expected to open in the first half of November. Downtown's open houses start November 5. Cookie Walk tins go on sale November 24 at 10 a.m., the Holiday Express refund window closes December 1, and the Christmas Walk lights up Main Street on Friday, December 4.
If all this new activity on Route 34 and Main Street has you wondering where your own home's value stands heading into the new year, the Lori Johanneson Team is happy to walk you through it over cocoa. Start with What's My Home Worth? and we'll take it from there.
