Street Art Festival

Schedule of Events:

Event Hours: 11:00 am - 6:00 pm
Street Art Competition: 9:00 am - 4:00 pm
Makers Market: 11:00 am - 6:00 pm
Kids Korner: 11:00 am - 5:00 pm
Judging: 4:00 pm
Awards: 5:30 pm

Artists Creating Art on the Streets:
Street Art Fest attendees will stroll the streets and watch as talented artists create artwork of amazing color, depth and complexity - with chalk! The Street Art competition will be judged at 4pm and winners will be announced at 6pm

Entertainment:
Local dance/cheer studios will take the stage and perform. Live music from local bands will fill the air!

Food & Drink:
Brats, burgers, hot dogs, bbq, nachos, ice cream, sno cones, funnel cakes, and MORE will be available for purchase!

Kristin's Concessions - Funnel cakes, elephant ears, pretzels

Highland Lion's Club - Brats, pork burgers, hot dogs

Highland Lion's Club

Highland Jaycees - Beer, soda, and seltzers

Mac's Gourmet Popcorn

Highland Tropical Sno

The Chocolate Affair - Homemade Ice Cream

Off The Rails BBQ - Pulled pork nachos & sandwiches, wings

Off The Rails BBQ

Taste of Balkan - Street corn, crepes, fruit salad

Taste of Balkan - Street Corn

Makers Market:
The Makers Market will include hand-crafted items by local artisans: soy candles and wax melts, macrame, pottery, glitter tumblers, acrylic wine glasses, handmade jewelry, custom hats, holiday decor and MORE!

Black Sheep Plant Co - Macrame Creations

Creations by JD - Inspirational signs

Handmade Crafts by Lynn - Sewn crafts & holiday decor

Marine Meadows - Hand-cut flowers and DIY bouquets

Meadow Branch Pottery - Hand-crafted stoneware

Mealtime Memories - Sourdough Micro-Bakery

Oh My Gaudy - Custom Trucker Hats

Wayne Brendel -Landscape paintings

Sips by Senter - Novelty drinkware

Sugar Creek Candle Co - Hand-poured candles and wax melts

The Sweet Spot - Novelty and nostalgic bulk candy

Urban Twist - Handmade and permanent jewelry

Kids Korner Activities: Sponsored by the Highland Optimist Club and organized by the Highland Civic Woman's Club
Kids will have their own special "Kreative Kids Korner" at this family-friendly event where they will have the chance to make their own works of art, play in a bounce house, and enjoy some imaginative fun and games!

Stop by the Musical Instrument Petting Zoo, hosted by the Highland Arts Center & Music School, where kids can see, touch, and try out a variety of real instruments - no lessons required, just curiosity! It’s a fun, hands-on way to spark a lifelong love of music.
Discover Downstate Illinois will offer an immersive experience for artists of all ages with their Monster Mural. Learn more about all their 21-county region has to offer while painting pieces of Downstate.

Bounce House

Craft Tent

Discover Downstate Monster Mural

Kids Chalk Art

Puzzle Blocks

Giant Tic-Tac-Toe

Kids Korner

Relaxing & Fun Hometown Environment:
Art, music, great food and beverages, all at Highland’s beautiful downtown square, combine to make this an annual event that you don't want to miss!!

View 2025's Street Art Fest Chalk Designs:

The Streets Literally Became a Canvas...

Street Art Fest 2025 was filled with color, creativity, and incredible talent! There were animals, landscapes, abstracts and a host of other pieces that mesmerized the attendees to the event! The artists knocked it out of the park with their chalk masterpieces! With so many outstanding pieces, it was no easy task for our judges - but after much deliberation, the winners were chosen.
Congratulations to this year’s champions!
VIEW ALL 2025 COMPLETED ARTWORK HERE