Dust off your sun hats and grab your bowties! Brooksville Main Street is thrilled to announce the next edition of the Downtown Street Market on Saturday, May 16th, 2026. This month, we’re bringing the spirit of the Bluegrass State to the heart of Florida with a high-energy Kentucky Derby theme.
Whether you're a fan of the "Run for the Roses" or just looking for a festive day out, this market is the perfect place to celebrate the home stretch of spring. From equestrian-inspired decor to the finest Southern hospitality, it’s going to be a winning day for the whole family!
The market will transform South Brooksville Avenue into a champion-level shopping experience. Attendees can explore a winner's circle of offerings, including:
Derby Style & Boutique Clothing: Find the perfect spring dress or dapper accessories.
Handcrafted Goods & Unique Gifts: Artisan-made items that are sure to place first in your heart.
Original Artwork & Home Décor: Refresh your living space with beautiful local creations.
Plants, Flowers & Produce: Seasonal blooms to keep your home looking vibrant.
Baked Goods & More: Local treats sweet enough for a southern social.
The Fun Doesn't Stop There: Visitors are encouraged to grab a bite from the featured food trucks, stroll through our historic district to visit downtown retail shops, and enjoy a leisurely lunch at one of our many brick-and-mortar restaurants. This event is family-friendly and pet-friendly, so bring the whole crew!