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November 2019

Shop Small Business Saturday 2019

November 30, 2019 @ 9:00 am - 6:00 pm
Historic Downtown Winter Haven Winter Haven, Florida + Google Map

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!

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December 2019

31st Annual Carols in the Park

December 7, 2019
South Central Park Downtown Winter Haven Winter Haven, Florida + Google Map

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…

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November 2020

Starlight Nights Downtown

November 25, 2020 @ 5:00 pm - January 6, 2021 @ 5:00 pm
Historic Downtown Winter Haven Winter Haven, Florida + Google Map

 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…

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Shop Small Business Saturday 2020

November 28, 2020
Historic Downtown Winter Haven Winter Haven, Florida + Google Map

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…

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May 2021

Bark in the Park 2021

May 28, 2021 @ 5:30 pm - 8:30 pm
Central Park Downtown Winter Haven Winter Haven, FL United States

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  

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July 2021

Treasure Hunt Downtown 2021

July 17, 2021 @ 11:00 am - 2:00 pm
Chamber of Commerce, 401 Ave B NW
Winter Haven, FL 33881 United States

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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November 2021

Wine Chocolate and Cheese 2021

November 12, 2021 @ 5:30 pm - 8:30 pm
Historic Downtown Winter Haven Winter Haven, Florida + Google Map

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…

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December 2021

Carols in the Park 2021

December 4, 2021 @ 10:00 am - 6:00 pm
Central Park Downtown Winter Haven Winter Haven, FL United States + Google Map

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…

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May 2022

Bark in the Park 2022

May 6 @ 5:30 pm - 8:30 pm
Central Park Downtown Winter Haven Winter Haven, FL United States + Google Map

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      

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June 2022

Craft Beer Crawl – Downtown Winter Haven

June 16 @ 5:30 pm - 8:30 pm
Central Avenue 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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