Monticello Fall Fest 2023 – Downtown, 21 N Main St., Monticello, KY, 12pm-9pm. The Chamber and Tourism are excited to announce that Fall Fest and The Main Street Project have combined this year to deliver a fun-filled day full of downtown fun. Complete with vendors, food, music, kids activities, and a community trick-or-treat, this is a day in Monticello that you won’t want to miss. Music features Martin McDaniel, Rye Davis and more. Info 606-348-3064 or www.facebook.com/theheartoflakecumberland.