Monticello Market Downtown – Car & Motorcycle Show 2026 – 11 N Main St., Downtown Monticello, 10am-3pm. Join the Chamber for their Downtown Market. The market will feature a variety of vendors from boutiques, beauty, crafts, fruit stands to food trucks. May features a Car & Motorcycle Show featuring cars, trucks, and motorcycles on display with awards at 2pm. For a vendor list & info 606-348-3064 or visit https://monticellokychamber.com/events/.