Latest Events

May 2022

The Whites of Spring 2022

5:00pm - 8:30pm CST

Downtown Monticello, 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 7 from 5-8:30 pm around historic, downtown Monticello. Wine sampling is reserved for ticketed guests, but all are invited to enjoy extended shopping hours, and visiting pop-up makers.
Once again, the map and wine glass pickup location will be in Wabash Depot (our tourism lobby and office location).  
Ticket sales will start on April 1st at 8 am and close May 3rd at 12 am, or upon sell-out, whichever comes first. 
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 2022

Reds of Christmas 2022 - Sold Out!

5:00pm - 8:30pm CST

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

Update: Thank you for your interest, however, this event has been sold out.  Here is a Google Map of the businesses participating on the day of the event, so even if you can't grab drinks, you sure can take advantage of the long shopping hours at each location!!
Jingle and mingle in Monticello this holiday season! There’s no better way to kick things off than with Reds of Christmas, a wine walk and shop event in our historic downtown. Ticketed guests check in and receive a commemorative tasting glass to pop in and out from spot to spot for red wine sampling and 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 of Monticello 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-