Latest Events

May 2023

The Whites of Spring 2023

4:00pm - 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 to downtown Monticello. Sample white wines as you walk, sip and shop participating merchants and restaurants.  Newly added will be a few appetizer locations! This event is on Saturday, May 6 from 4-8:00 pm around historic, downtown Monticello. Wine sampling is reserved for ticketed guests, but all are invited to enjoy extended shopping hours.
The map and wine glass pickup location will be in CIBM Bank at 204 S Market St. Monticello IL 61856 starting at 4 PM.
Huge thanks to CIBM Bank as our event sponsor!!  Thanks as well to Bespoke Gift Company for their help with the glasses!
For a little added fun, we encourage everyone to wear their best Derby-inspired hats for a bit of fun that day!  While you're at it, grab a selfie with your group using the hashtag #makeitmonticello to be entered in a drawing for $50 of Chamber Bucks, to spend on your next visit to our beautiful downtown, thanks to the Monticello Area Chamber of Commerce!!

November 2023

Reds of Christmas 2023 - Sold Out!

5:00pm - 8:00pm CST

Historic Courthouse Square in Downtown Monticello, Monticello, IL, 61856

This event is now sold out, however, you can still join us to enjoy the atmosphere and shopping on Friday...without wine, appetizer, or dessert tastes.
Come mingle with old friends in Monticello this holiday season! There’s no better way to kick things off than with Reds of Christmas, a shop-walk with fifteen wine tastes, along with appetizer and dessert tastes along the way in our historic downtown. Ticketed guests will receive a commemorative tasting glass at check-in to use for red wine sampling while they are shopping.
Tickets are $25 and are available online only. Ticket sales will close one week prior to the event, or upon sell-out, whichever comes first. A final map of participating shops will be provided at the event. 
Special thanks to our sponsor First State Bank and Trust for their support of this event!!  We also want to thank Bespoke Gift Company for their partnership with Monticello Main Street for this event!


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Monticello Main Street
P.O. Box 392
(217) 762-9318


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 | Copyright © 2006-