| May 2025 | |
| 09 Friday | The Whites of Spring 20255:00pm - 8:00pm CST CIBM Bank, 204 S Market, Monticello, IL, 61856 A Refreshing Way to Enjoy Historic Downtown Monticello The Whites of Spring celebrates the arrival of Spring in downtown Monticello. Sample white wines as you walk, sip, and shop at participating merchants and restaurants. There will also be a few appetizer locations! This event is on Friday, May 9, from 5 - 8:00 pm around historic downtown Monticello. Wine sampling is reserved for ticketed guests, but all are invited to enjoy extended shopping hours. The printed map and wine glass pickup location will be in CIBM Bank at 204 S Market St., Monticello, IL 61856, starting at 4 PM. We ...more |
| November 2025 | |
| 28 Friday | Reds of Christmas 20255:00pm - 8:00pm CST Historic Courthouse Square in Downtown Monticello, Monticello, IL, 61856  Mingle with old & new friends alike in Monticello this holiday season! There’s no better way to kick things off than with the First State Bank and Trust Reds of Christmas, a shop walk with wine, appetizers, and dessert tastes throughout our historic downtown. Ticketed guests will receive a commemorative tasting glass at check-in for red wine sampling while shopping.
Tickets are on sale at 3 PM on October 31, 2025!
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| December 2025 | |
| 18 Thursday | Candles & Carols 202505:00 PM - 8:00pm CST Downtown Monticello, 110 S State St, Monticello, IL, 61856  Come to Downtown to enjoy a community celebration! Make some family memories for the holidays!
5 - 8 PM:
Horse-Drawn Carriage Rides available!
Local Retailers and Restaurants are open for last-minute shopping!
Grab a selfie for fun holiday photos in Rotary Park!
6:00-7:30 Join in a Community Carol Sing-a-Long!! Make some family memories for the holidays!
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Downtowns thrive on what you can see when you’re here.
When people are walking, browsing, and spending time downtown, it doesn’t just feel lively—it becomes more vibrant. That’s why seeing people in downtown Monticello matters. Every sidewalk conversation, every window shopper, every patio seat filled helps tell the story that downtown is active, welcoming, and worth exploring.
A busy downtown isn’t just a nice moment—it’s momentum.
Monticello is fortunate to have such a strong and “healthy” healthcare base right here in the community. The Main Street organization appreciates Christie Clinic's investment in downtown Monticello and their continued longevity as a trusted part of our local landscape.
It’s National Public Works Week, and we truly couldn’t do all the things we do without the support of Mayor Stoner and the @City of Monticello, Illinois Government Public Works Department. From parklet installation to keeping our streets clean and looking their best, their attention to detail helps keep our downtown district running smoothly—and looking good while doing it.
Design is one of the four cornerstones of the Main Street program, helping ensure the historic integrity of our National Historic District is preserved. It also supports thoughtful integration of public art, beautification, and seasonal décor that enhances downtown’s character while keeping its history front and center.