"On Sundays, there's not a coffee option for downtown shoppers, which in the past has impacted customers for other businesses." That's how Jes Meingasner, executive director of the Milan Downtown Development Authority, explained the DDA's newest program to The Sun Times News in August.
Her answer was Sundays on Main. Milan City Council approved a $500 special event request on Aug. 3 that allows up to two food trucks to set up downtown every Sunday from Aug. 9 through Dec. 27. Today is Sunday, Oct. 11, so eleven Sundays are left on that schedule.
Most of the fall and holiday calendar downtown runs on evenings and Saturdays. Each event has its own organizer, and most get a single night. Sunday is the gap in that calendar, and it's the only part of the schedule that runs every week.
The Sunday Gap, and Why a Truck Fills It
Downtown Milan's other events bring a crowd for one evening and then pack up. Sundays on Main works differently. It's meant to fix a regular weekly lull. In the DDA's account, the problem is bigger than the missing latte. Shoppers with no coffee stop downtown on a Sunday spend less time there, and other businesses feel it.
Caffeine & Crumbs opened the series at 11 a.m. on Aug. 9. Meingasner named Bear Truck Coffee and Dora's Donuts as vendors for the weeks after. She also told The Sun Times News that the DDA picks trucks carefully so they don't compete with existing downtown businesses. They also want trucks that do well enough to come back.
The program has no fixed end beyond the approved Dec. 27 date. "We're going to ride it for as long as we have trucks," Meingasner said, adding that she hopes residents will support the trucks if they want the series to continue. We couldn't find a published October vendor roster or a confirmed list of trucks for the coming Sundays, and the Sundays don't appear on the online October event calendar. Treat each Sunday as scheduled but not guaranteed. The DDA's own description makes the series depend on whether trucks keep signing up and customers keep coming.
Two Parking Spaces at the Top of Wabash
On any given Sunday, the trucks park in the first two parking spaces at the top of Wabash Street, near the bike rack and The Play Station.
That location fits the DDA's goal. The Play Station describes itself as a family-friendly indoor play space downtown, with a children's climbing structure, magnet tiles, a gymnastics area and a café area. Putting a coffee truck next door places Sunday coffee right beside one of the downtown businesses most likely to draw families on a cold weekend morning.
For a sit-down breakfast or lunch on a Sunday, Campfire Grill at 1035 Dexter Street is another choice. The Sun Times News reported in January that the restaurant opened under that name after an earlier partnership dissolved, with a scratch-made menu and hours of 7 a.m. to 9 p.m. daily except Tuesday.
October Runs on Evenings, and Several Organizers
Weeknight and Friday evenings are a different story. Downtown Milan's October has a full calendar, and nearly every event comes from a different organization. That's why the only weekly anchor needed the DDA and City Council to approve a new program.
The scarecrows already on Main Street are the work of the Milan Area Historical Society. The Sun Times News described witches, football players, a beekeeper, monsters and pumpkins. Voting is open until noon on Oct. 30 in the 2026 Scarecrows on Main album on the Historical Society's Facebook page. Likes, comments and shares on the original photos each count as a vote.
The rest of the month, in order:
- Thursday, Oct. 15, 5 p.m.: Practically Magical Girls Night Out downtown, with shopping, giveaways, food trucks and music.
- Friday and Saturday, Oct. 23–24: The Haunted Bus Tour & Murder Mixer, a Moving Milan Forward event with Milan Theatre Co. The listing names The Owl, 9 W. Main St., as the venue, says tours run 7 to 10 p.m. both nights, and places Saturday activities in Tolan Square and The Owl.
- Friday, Oct. 30, 5:30–7 p.m.: Downtown Trick or Treating, presented by Dynamic Drains. The Milan Area Chamber of Commerce says merchants and community groups will hand out treats, with the event centered at Tolan Square, 1 E. Main St.
Trick or Treating falls on the same day scarecrow voting closes at noon. A family walking downtown that evening can see the finished displays before the results are announced.
The November Night Away From Main Street
The biggest event of early November isn't downtown. Aid in Milan holds its 10th Annual Empty Bowls on Monday, Nov. 9, from 6 to 8:30 p.m. at Milan Free Methodist Church, 950 E. Arkona Road. According to the 2026 fundraiser page, the event raises money and awareness to help local families facing food insecurity get food and other resources.
It also fills a stretch the downtown calendar leaves quiet. Between Trick or Treating on Oct. 30 and the vendor fair on Nov. 28, the downtown listings we reviewed show no other evening event. For four weeks, Sundays on Main is the only scheduled thing happening downtown.
Three Saturdays That Close Out the Year
From Small Business Saturday on, the calendar moves to Saturdays. The last three Saturdays fall one week apart, and each starts at a different time of day.
| Date | Event | Start | Where |
|---|---|---|---|
| Sat., Nov. 28 | Pop On Main vendor fair | 8 a.m. | The Center |
| Sat., Dec. 5 | Downtown Milan Holiday Parade, presented by Hungry Howie's | 6 p.m. | Downtown |
| Sat., Dec. 12 | Moonlight Madness | 6 p.m. | Downtown |
Pop On Main is described as a Small Business Saturday collaboration with vendor shopping. The parade listing doesn't name an organizer beyond its presenting sponsor. Moonlight Madness promises late shopping, food trucks and vendors, though its page notes more details are still to come. Check that listing again closer to Dec. 12.
Each of these Saturdays is followed by a Sunday that's on the food-truck schedule: Nov. 29, Dec. 6 and Dec. 13. If the trucks keep coming, the busiest downtown weekends of the year will have coffee on both days. The approved run ends on Sunday, Dec. 27, two days after Christmas.
The Work Going On Under and Around the Streets
Two city projects add a different kind of activity to downtown this fall, and neither one is an event.
The first is fiber internet construction. In an Aug. 12 notice, the City of Milan said companies would begin installing fiber as early as mid-July, with digging and boring expected in several areas. It also said five METRO Act permits had been approved in the previous month. The city noted that its control over the exact timing and placement of this right-of-way work is limited, and it didn't name the providers or give completion dates.
The second is still only a plan. On Aug. 19, the city announced a $35,000 SEMCOG award for a corridor-planning study. Topics proposed for it include rerouting trucks, pedestrian safety and downtown parking. The award pays for a study, not construction, and the announcement gave no schedule. The study takes up the same questions behind Sundays on Main, from the opposite end. The DDA's trucks are a small, low-cost way to bring people downtown on the slowest day. The corridor study looks at how people, trucks and parked cars share Main Street at all.
For now, the two parking spaces at the top of Wabash are the experiment you can actually see. Whether they're still in use on Dec. 27 depends, by the DDA's own account, on whether trucks keep showing up and customers keep buying from them.
If you live in Milan and are thinking about what's next, whether that means a move across town or staying closer to a downtown that's adding to its calendar, Stephen Hollowell is glad to talk through how Milan's blocks and streets differ. Schedule a free consultation, and bring your questions over coffee.
