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September 2018
Ladies Night Downtown
Ladies Night Out Downtown Winter Haven Thursday Night SEPTEMBER 6. This is a FREE event, come to the corner of 4th Street and Central (across from Wauchula State Bank) to pick up your map of participating downtown business who will be open from 5:30-8:30 offering shopping, dining and cocktail specials! RSVP below to save your spot!
Find out more »November 2018
Wine, Chocolate & Cheese
Tickets are no longer available online. You can still purchase tickets using cash or card at the location below. See you there!
Find out more »June 2019
Craft Beer Crawl Downtown 2019
Come explore Downtown Winter Haven while trying over 25 specialty craft beers in our participating shops and businesses! Preorder your tasting mug and map online and pick them up on the corner of Central Ave and 4th Street NW at 5:30PM to begin the crawl. CLICK HERE TO PURCHASE TICKETS
Find out more »August 2019
Ladies Night Downtown 2019
Enjoy a night of shopping, dining, and cocktail specials in participating businesses Downtown Winter Haven. Register for your FREE map online and pick them up on the corner of Central Ave and 4th Street NW at 5:30PM. Reserve your map BELOW:
Find out more »November 2019
Shop Small Business Saturday 2019
Come out and support your local small businesses in Downtown Winter Haven on November 30th! Be sure to visit each of the participating businesses and pick up some unique goodies for your holiday shopping!
Find out more »December 2019
31st Annual Carols in the Park
31st Annual Carols in the Park presented by Citizens Bank and Trust December 7, 2019 10AM - 7PM Main Street Winter Haven is thrilled to announce our 31st Annual Carols in the Park presented by Citizens Bank and Trust! For over thirty years, artisans, specialty food vendors, and local choral groups have gathered in Downtown Winter Haven’s Central Park to kick off the holiday season. This event has become a tradition for multiple generations, with a special Candy Cane Corner…
Find out more »November 2020
Starlight Nights Downtown
Main Street Winter Haven & The City of Winter Haven are thrilled to announce Downtown's Winter Haven's newest Holiday tradition - Starlight Nights! For six weeks, Downtown Winter Haven will be dazzling with lights as we ring in the season of Holiday cheer and togetherness. Dine, shop, and enjoy a beautiful evening stroll with fun photo opportunities and surprises around every corner. You'll be able to explore the magic of the lights at your own comfort level, whether you'd rather…
Find out more »Shop Small Business Saturday 2020
Come out and support your local small businesses in Downtown Winter Haven on November 28th! Be sure to visit each of the participating businesses and get an early start on holiday shopping! Shop Small Scavenger Hunt: 1. Pick up your Shop Small Scavenger Hunt map at any of the participating businesses, or download the image below! 2. Visit as many of the stops on the scavenger hunt as you can! Each stop will have a staff member to sign off…
Find out more »May 2021
Bark in the Park 2021
It’s a dog day in Downtown Winter Haven! Spend your FREE Friday night shopping pet vendors, enjoying a cold beverage, and enjoying time with your favorite four-legged friends. This year's event will be held in Central and South Central Park Downtown - with favorites like the police K9 demonstration and our Annual Weiner Dog Race! See you there! VENDOR APPLICATION CLICK HERE
Find out more »July 2021
Treasure Hunt Downtown 2021
Main Street Winter Haven, in partnership with our Downtown businesses, presents our Annual FREE Treasure Hunt Downtown. Children under the age of 12 will search for LEGO® Minifigures in the participating locations Downtown! Pick up your FREE treasure map from the Chamber of Commerce Breezeway between 11AM-1PM. Participating downtown businesses will hide a LEGO® Minifigure inside their business. Once you have spotted the LEGO® Minifigure, tell the business owner and they will mark your map. After all stops have been…
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