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  • Downtown Dining Week

    Historic Downtown Winter Haven Winter Haven, Florida

    Get ready for a culinary adventure at the inagural Downtown Dining Week in Downtown Winter Haven from August 15th through 25th! This event is your chance to explore a variety of flavors and dishes from over 20 participating restaurants, each offering exclusive specials at irresistible price points! Whether you're in the mood for a casual […]

  • Shop Small Business Saturday

    Historic Downtown Winter Haven Winter Haven, Florida

    Small Business Saturday® in Downtown Winter Haven Join us in the heart of Winter Haven as Main Street Winter Haven proudly hosts Small Business Saturday®, a festive event dedicated to supporting our local community. Embraced by the spirit of small businesses, this event takes place in Historic Downtown Winter Haven. We are proud to be […]

  • Main Street Monsters

    Historic Downtown Winter Haven Winter Haven, Florida

    We are excited to announce - Main Street Monsters 2026  This month-long scavenger hunt will be held in Downtown Winter Haven beginning July 1st. Main Street Monsters is a FREE event where families are invited to find the hidden friendly monster murals scattered throughout Downtown. This exciting event combines art and technology by engaging kids […]