Craft Beer Crawl 2023

Historic Downtown Winter Haven Winter Haven, Florida

A long time ago in a Downtown far, far away....or right here in your community! Main Street Winter Haven invites you to celebrate May the Fourth with good friends and […]

Bark in the Park 2023

Central Park Downtown Winter Haven Winter Haven, FL, United States

Spend your FREE Friday night shopping pet vendors, enjoying a cold beverage, and enjoying time with your favorite four-legged friends. Bark in the Park will be held in Central and […]

Wine, Chocolate & Cheese

Central Avenue Downtown Winter Haven

Main Street Winter Haven hosts our 9th Annual Wine, Chocolate, and Cheese event in Downtown Winter Haven, on November 3, 2023, from 5:30-8:30 PM! We invite you to explore Downtown […]

Starlight Skating – Downtown Winter Haven

Get ready to glide into the holiday spirit as an enchanting ice skating rink arrives in Downtown Winter Haven for two unforgettable days on December 2nd and 3rd! Join us […]

Starlight Stroll – Downtown Winter Haven

Join us for an evening at the heart of downtown Winter Haven and partake in the Starlight Stroll! Experience the magic of the Holiday Season as the city comes alive […]

Sidewalk Shopping – Downtown Winter Haven

Join us for a festive day of shopping and holiday cheer in Downtown Winter Haven! On December 16th, from 10am to 2pm, Central Avenue comes alive with a sidewalk shopping […]

CityWorksXpo Florida – 2024

Historic Ritz Theater 263 W Central Ave, Winter Haven, FL, United States

CityWorksXpo Florida is a gathering focused on sharing knowledge to build stronger communities. During the day, attendees will be immersed in thought-provoking presentations, performances and engaging dialogue. At night, the […]

Beer & Bubbles

Historic Downtown Winter Haven Winter Haven, Florida

Join us for Main Street Winter Haven's Beer and Bubbles presented by Bank of Central Florida! Discover the charm of our city as you stroll through downtown, sampling an array […]

Main Street Monsters

Historic Downtown Winter Haven Winter Haven, Florida

We are excited to announce - Main Street Monsters 2024 presentd by Citizens Bank & Trust! This month-long scavenger hunt will be held in Downtown Winter Haven beginning July 1st. […]