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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…
Find out more »November 2021
Wine Chocolate and Cheese 2021
Main Street Winter Haven hosts our annual Wine, Chocolate and Cheese event in Downtown Winter Haven on November 12, 2021! On Friday, November 12th over 30 Downtown businesses will host a wine & chocolate or a wine & cheese pairing. Your Tasting Passport will take you from business to business to sample each of the combinations! Live music on the street makes for a great night to explore Downtown with friends while enjoying great wine & bites. Tasting tickets can…
Find out more »December 2021
Carols in the Park 2021
32nd Annual Carols in the Park presented by Citizens Bank and Trust December 4, 2021 10AM - 6PM Main Street Winter Haven is thrilled to announce our 32nd 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 »May 2022
Bark in the Park 2022
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 »June 2022
Craft Beer Crawl – Downtown Winter Haven
Come explore Historic Downtown Winter Haven while sampling specialty CRAFT BEERS & BITES 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 to begin the crawl! Special thank you to our presenting sponsor Bank of Central Florida! Tickets are $25 and include a tasting mug and sample tastes of over 30 craft beers and bites 🙂 TICKETS AVAILABLE HERE
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