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October 2019
13th Annual Oktoberfest
🍻Main Street Winter Haven's 13th Annual Oktoberfest presented by Victor Smith Law Group will kick off October 18th at 6:00PM in South Central Park - complete with over 40 Florida Craft and German beers! Local Florida breweries will be joining in on the fun - pouring their signature and Oktoberfest style beers! Rick's BBQ and Nutwood will be grilling brats, bbq, pork sandwiches and more. If you are in the mood for wine, grab a glass of Riesling or Pinot…
Find out more »November 2019
Wine Chocolate and Cheese 2019
Main Street Winter Haven hosts our annual Wine, Chocolate and Cheese event in Downtown Winter Haven! 🍷🍫🧀 Main Street Winter Haven invites you to enjoy our annual Wine, Chocolate & Cheese event on Thursday, November 21, 2019. Over 35 downtown businesses will host a wine & chocolate or a wine & cheese pairing. Your Tasting Passport allows you to choose which 25 curated pairings you would like to try. Live music on the street makes for a great night to…
Find out more »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 »March 2020
CityWorks(X)po – Florida
(X)po is a collaborative, co-creative, and multi-disciplinary idea exchange and festival conference occurring annually in Roanoke, Virgina. Main Street Winter Haven is partnering with Greater Winter Haven Chamber of Commerce, City of Winter Haven, Winter Haven Economic Development Council and Visit Central Florida to bring you this exciting conference. Attendees are immersed in thought provoking presentations, riveting performances and engaging dialogue. By night the conference continues with networking opportunities at amazing parties, street-fests, and spectacular live music. Your registration includes…
Find out more »St. Patrick’s Day Celebration
🍀It's a St Patrick's Day Celebration! 🍀 Grab your family and friends, put on your best green shirt, and enjoy performances from Orlando's Celtic Band LOCHLANN and Central Florida Irish Dance School! **Make sure you bring a law chair or blanket to enjoy the show! This St. Patrick's Day Celebration will feature: 💃🏼FREE Show (*bring a chair or blanket) 🥙Food Trucks (with traditional Irish goodies) 🍺Beer & Wine Tent (GREEN beer!) 🎨Kids Games & Crafts ☘️And a Roaming Bagpiper!! Special…
Find out more »July 2020
Treasure Hunt Downtown
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! 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 completed, you will turn in your map to to the treasure chest located in…
Find out more »September 2020
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…
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