Monticello
COMMUNITY GUIDE 2026
Streets become works of art at Let’ s Chalk
One of Monticello’ s newest signature events is truly something to chalk about. Let’ s Chalk, a two-day street art festival, transforms downtown Monticello each year in late summer or early fall, turning Walnut and River streets into a vibrant, open-air art gallery.
Often referred to as“ Chalkfest,” the event invites professional and amateur artists from across the United States to create large-scale works directly on the pavement, allowing visitors to watch the art come to life in real time. Bright, bold designs line the streets, ranging from traditional illustrations to striking 3D illusions that appear to leap off the ground and regularly become favorite photo spots for festivalgoers.
Let’ s Chalk was founded in 2022 through a collaboration between nationally recognized chalk artist Shawn McCann and Monticello Mayor Lloyd Hilgart. McCann, a professional street artist and muralist based in Minneapolis, brought extensive experience from chalk festivals across the country, while Hilgart provided local leadership, vision and community connections that helped bring the event to Monticello.
From the start, the festival was designed to be both a high-quality arts event and a welcoming community gathering. Each year, dozens of artists participate, blending nationally known chalk professionals with regional, local and student artists. That mix gives Let’ s Chalk a distinctive character, pairing gallery-level artwork with a strong hometown feel.
While chalk remains the primary medium, many artists incorporate paint and pastels into their work, pushing the boundaries of street art. Creating the artwork is a physically demanding process, with artists spending long hours outdoors and often ending the day covered in color as their pieces take shape. The temporary nature of the art— destined to fade with time and weather— adds to the festival’ s appeal, making each edition a one-of-a-kind experience.
Beyond the artwork itself, Let’ s Chalk offers a full slate of family-friendly activities. Children are encouraged to create their own chalk drawings, while live music, interactive installations and hands-on art experiences keep the downtown lively throughout the weekend.
Food and beverage offerings are intentionally sourced exclusively from Monticello businesses, reinforcing the festival’ s role as a local showcase. Organizers have emphasized keeping the event community-centered, spotlighting local restaurants and vendors alongside visiting artists.
The festival also highlights Monticello’ s evolving downtown, activating River Street, West Bridge Park and nearby businesses with art, music and foot traffic. Equal parts art exhibit, street celebration and community gathering, Let’ s Chalk has quickly become a standout addition to Monticello’ s annual events calendar and a colorful example of how creativity can bring people together.
MONTICELLO COMMUNITY GUIDE | 2026 | 17