Monticello Main Street

Latest Events

Year

Upcoming events

October 2026
31 Saturday	Merry on Main All day event CST
November 2026
27 Friday	Reds of Christmas 2026 5:00pm - 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 & Trust Reds of Christmas, a shop walk with fifteen wine tastes, along with appetizer 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 $30 per person. They are available online only. Ticket sales will close upon sell-out. A printed Map will be provided to ticket holders; a Google map will be available here! Visitors without tickets will not receive tastes at each location, but are welcome to shop and enjoy the festive atmosphere with our ticket holders! Special thanks to our sponsor, First State Bank and Trust, for their support of this event!! As well as our wonderful participating businesses: Monticello Mercantile Soy & Lee Clothing Boutique These Four Walls Out of the Blue Polish Pottery En Pointe Yoga Off the Square There's No Place Like Home Stewart Family Hardware Lilly's Flooring Friend$ Video Gaming Parlor
December 2026
18 Friday	Take a Pause before the Clause 05:00 PM - 8:00pm CST Downtown Monticello, 110 S State St, Monticello, IL, 61856 Step away from the hustle, take a breath & enjoy some downtown holiday magic! 5 - 8 PM: Horse-Drawn Carriage Rides Strolling Carolers Enjoy the holiday vibe and grab a selfie in Rotary Park Grab a bite to eat at one of our restaurants! If you and your friends want to carol, we'd love to have you, and we even have a digital songbook you could use! Keep watching this event and our page for information on any restaurant or retail specials and businesses open for last-minute shopping! Songbook

>

ABOUT MONTICELLO MAIN STREET

Home
Events
About Us
B ecome a Partner

SOCIAL

CONTACT US

Monticello Main Street
P.O. Box 392
(217) 762-9318 info@monticellomainstreet.org

SIGN UP FOR OUR NEWSLETTER

Monticello Main Street, Inc. is a nonprofit program of The National Trust for Historic Preservation, dedicated to the revitalization of our historic downtown. Monticello is accredited both as an Illinois and National Main Street community. Monticello Main Street © | PO Box 392, Monticello, IL 61856 | Tel: (217) 762-9318 | Fax: (217) 762-9713 | info@monticellomainstreet.org Copyright © 2006-2026