| 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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Are you still looking for that awesome gift?? Then be sure to swing by Monticello Mercantile when you visit Monticello for 2025 Reds of Christmas this year!
Don't wait to grab tickets...this event sells out each year!
This event is a fundraiser for Monticello Main Street. Monticello Main Street is a 501c3 organization, celebrating its 30th anniversary in 2026, dedicated to historic preservation and strengthening our community's economic growth. Learn more at our website!
We’re coming home from the Illinois Main Street State Conference with some awards!!
Our program received an Award for Excellence in Economic Vitality in recognition of our 10 years operating the Monticello Bootcamp and recognized the incredible work of Board President Susan Kesselman!!
Monticello Bootcamp helps entrepreneurs learn about what it takes to operate a business successfully. It is a key factor in Monticello’s business growth and full downtown! This program was championed by Past Executive Director Kerry Redshaw and has been faithfully operated by Callie McFarland from City of Monticello, Illinois Government (and current Board Member) the past 10 years! We’re lucky to have leaders with vision and commitment!!
Susan must be known by everyone! She’s tireless in her support of all things Monticello. She is at almost all the Monticello Farmers' Markets each season and is always available to lend a helping hand to shoppers and vendors! This year she is our Board President and we couldn’t do it all without her!!
It’s wonderful to be recognized by your peers and the program we’ve been a part of for almost 30 years!!
Main Street America
We've often promoted our friend Kat Ryan and her book series set in a fictional town that is loosely based on our beloved community. She has her 9th book in the series out now! So if we previously sucked you into her world...run out and grab the next book!