Highland's Fall Runs Through the Square This Year. Here's Who Is Putting It On.
October 15, 2026
October 15, 2026
On Friday, Oct. 30, barricades will close the Highland Square and Washington Street from Main to 9th. From 1 to 5 p.m. a sound system will play on the Square while businesses hand out candy from tables there or from their own storefronts. The application filed with the city expects "1000+" kids. It also has a box for asking the City Council for money, and that box is marked no.
That form is a good guide to the rest of Highland's fall. Nearly every confirmed event between now and Thanksgiving weekend happens on or near the Square at 914 Main St., and each one comes from a local business, civic club, chamber, or charity that applied to the city for its date. The city approves the permits, closes the streets, and keeps the calendar. The events themselves come from other people.
The rest of this post covers who is behind each event and what to expect when you get there.
The application for Treats on the Streets lists the Rinderer Law Firm and Highland Optimist as sponsors. Marshall Rinderer of the firm's office at 907 Washington St. is the responsible party. The event is listed as business-to-business trick-or-treating, so the candy comes from the shops and offices themselves. Participating businesses can set up on the Square or stay at their own locations. The City Council approved the event and the street closures around the Square at its Sept. 8 meeting. The city's celebrations page describes the tradition as costumed trick-or-treating for kids under 12 on the Friday before Halloween.
The time is the detail to plan around. A 1 to 5 p.m. window on a Friday means school pickup, work schedules, and costume changes all come into play, and the closure of Washington Street from Main to 9th affects anyone who usually cuts through downtown that afternoon. The Times Tribune reported the same date and the same estimate of about 1,000 children.
The Saturday after Treats on the Streets is a different story. If you search for Highland Halloween events, you will probably find the Parks and Recreation page for a "Halloween Candy Trail" at Glik Park on "Saturday, October 31st," from noon to 5 p.m., with a pumpkin carving contest. The page opens with "Mask up," and its business participation letter is dated Sept. 1, 2020. Oct. 31 falls on a Saturday this year too, which makes the old page look current. The city's October 2026 calendar lists Treats on the Streets on the 30th and nothing on the 31st. Until Parks and Recreation posts a 2026 date, Friday downtown is the confirmed Halloween event.
For younger kids who want a costume run earlier, the Louis Latzer Public Library is holding Halloween Bingo for ages 3 and up on Thursday, Oct. 22, at 6 p.m. Costumes are welcome and there are prizes.
The earliest event on the calendar is at 5 a.m. on Saturday, Oct. 17, when the Illinois statewide fall trout season opens. The Illinois Department of Natural Resources lists Highland Old City Lake in Madison County as one of its stocked sites. According to the IDNR catchable trout program, no trout may be taken before the opener and the daily limit is five. Anglers need a fishing license and an inland trout stamp unless they are exempt. The state also notes that opening times can vary by site. IDNR stocks more than 80,000 rainbow trout statewide each fall but does not say how many go to Old City Lake.
The Highland Chamber of Commerce is holding a Business After Hours on the Square for members and guests, and it's the one fall date where the sources disagree. The City Council minutes approve it for 5 to 8 p.m. on "Thursday, October 14, 2026," but Oct. 14 is a Wednesday. The Times Tribune reports Thursday, Oct. 15, where the date and the weekday agree. If you're going, confirm the date with the Chamber.
Highland Community Closet runs the November event. The group describes its work as providing essentials to people who need them. Its second annual Soup on the Square is approved for Saturday, Nov. 7, on the north side of the Square from 11 a.m. to 2 p.m. The council record notes that last year's event served 1,400 portions.
That's a lot of soup for a three-hour lunch, especially since the 2026 Treats on the Streets application expects "1000+" kids. The meal is free. The organizer's event listing adds bounce houses, live music, food trucks, vendors, and a kids' vendor corner. It also includes a coat and blanket swap: you can bring coats or blankets to donate and take anything from the donation tent, and you don't have to bring anything to take something. Donations are welcome but not expected, and any proceeds go toward next year's event.
On timing, the organizer's public listing says 10 a.m., while the council approval says 11 a.m. The city-approved 11 a.m. start is the safer one to plan around unless the Community Closet posts an update.
The same pattern of private effort shows up in the buildings around the Square. Cousins Tricia Feyerabend and Shannon Hogg bought a roughly 150-year-old building at 923 Main St. about three years ago. Since then they have turned it into Towne Square Terrace, which holds Hogg's JusTeazin' Salon and Boutique, an upstairs short-term rental run by Feyerabend, and now a new event venue in what used to be an aging garage and overgrown backyard, the Times Tribune reported in July.
"There isn't really a small event venue like this in Highland anymore." Tricia Feyerabend, to the Times Tribune
The venue holds up to 80 seated guests indoors and outdoors, and glass garage doors open onto a covered patio. Renters bring their own food, drinks, decorations, and vendors. The owners also offer the space on weekdays for nonprofit meetings and community gatherings. An exposed brick wall from the original building is the centerpiece inside, and bricks saved from the demolition were cleaned and reused on the new exterior.
The project used Highland's façade improvement program. The program started after the pandemic and covers up to 25% of eligible exterior renovation costs in certain areas of town, with a cap of $10,000 per project and a minimum project size of $10,000. The structure follows the same pattern as the events. The city puts in a set share, and the owners pay for the rest and do much of the finishing work themselves. Their family stained the lumber, painted, refinished furniture, and poured the concrete countertops.
The Highland Chamber's Lighted Christmas Parade has its 2026 theme, "Star Spangled Christmas," and a 6:30 p.m. start. The Chamber's parade page still says the full announcement is "coming SOON!" and doesn't list a date. The city's lighting-ceremony application, on the agenda for the Oct. 5 council meeting, schedules the Square lighting for Nov. 27, after the parade ends. That points to the Friday after Thanksgiving, but the Chamber hasn't confirmed it.
That puts the Chamber on the Square twice this fall, once for a business mixer in October and once for the parade in November. A law firm and a civic club put on Halloween, and a charity serves the November lunch. Together they fill the downtown calendar from the trout opener to the tree lighting.
Our team follows the Square closely, including the events, the new venues, and the city programs that support them. Whether you're thinking about an exterior project like the one at 923 Main St. or wondering how downtown activity shows up in what nearby homes are worth, Wylde Realty Team can give you a clear, local answer. Contact Us whenever it's convenient.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
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