| 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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Main Street Facebook
Friend$ is always a great stop during 2025 Reds of Christmas. Consider doing some shopping for that cigar smoker or gambler among your family! You can also simply stop and have a drink with your friends!!
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!
Books are always just the ticket for that hard-to-shop-for person. Hartfield Book Co.even has a title for all of us stressed-out Christmas magic-making individuals!! Be sure to swing by during 2025 Reds of Christmas!
Don't miss out on this fun annual event...tickets are selling out quickly!
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 are honored that En Pointe Monticello calls Monticello home and will be participating in 2025 Reds of Christmas!! It's hard not to feel in the spirit of the season when surrounded by the trappings of the Nutcracker!! They will have all the things that your tiny, or bigger, dancer might need...but they often have some beautiful ornaments and other items non-dancers might enjoy!
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!
You may not have heard...but Willow Tree Missions has added a Christmas Store to their locations. This is the place to visit if you are looking for the perfect Christmas decoration to finish your look at home!! We're thrilled to have them as a part of 2025 Reds of Christmas!
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!