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April 2019

CityWorks(X)po Florida 2019

April 3 - April 4
Ritz Theater, 263 W Central Ave
Winter Haven, FL 33880 United States
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CityWorks(X)po 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. By night, the all inclusive conference continues with networking opportunities at high energy and (X)citing events. CityWorks(X)po FLorida provides a platform for sharing knowledge, stories, ideas, and projects with a focus on strengthening cities of all sizes. Attendees will represent communities from across the state of Florida. (X)po is about connectivity between people,…

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May 2019

Bark in the Park 2019

May 3 @ 6:00 pm - 9:00 pm
Central Park Downtown Winter Haven Winter Haven, FL United States + Google Map

It’s a dog day in Central Park Downtown Winter Haven! Spend your FREE Friday night shopping pet vendors, listening to music, and enjoying time with your favorite four-legged friends. Annual wiener dog race at 7:30PM. See you there! Sponsorship Application Form

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June 2019

Craft Beer Crawl Downtown 2019

June 20 @ 5:30 pm - 8:30 pm
Historic Downtown Winter Haven Winter Haven, Florida + Google Map

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

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July 2019

Treasure Hunt Downtown 2019

July 20 @ 11:00 am - 2:00 pm
Chamber of Commerce, 401 Ave B NW
Winter Haven, FL 33881 United States
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Main Street Winter Haven, in partnership with our downtown businesses, presents our annual FREE Treasure Hunt Downtown. All you need to do is register for the free map, children under 12 years of age please. Check in between 11 AM – 12:30 PM inside covered breezeway of the Chamber of Commerce (located at 401 Ave. B NW, Winter Haven FL 3881) and get started with your adventure! Participating downtown businesses will hide a LEGO® Minifigure inside their business. Once you…

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August 2019

Ladies Night Downtown 2019

August 29 @ 5:30 pm - 8:30 pm
Central Avenue Downtown Winter Haven

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:

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September 2019

Bourbon and Blues 2019

September 27 @ 6:00 pm - 9:00 pm
Gram Parsons Derry Down, 297 5th Street NW
Winter Haven, FL 33881 United States
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Please join us for a night of Live Blues, Premium Bourbon Tasting, Great BBQ, Grove Roots Brewing Co., beer, Wine, Cocktails, and a Signature Mocktail on September 27, 2019, 6 PM. You won't want to miss the silent auction! MSWH thanks you for your support! This event is a fundraiser for Main Street Winter Haven a not for profit 501(C)(3). All proceeds from this event will go to support Gram Parsons Derry Down. The MSWH Board of Directors is proud…

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October 2019

13th Annual Oktoberfest

October 18 @ 5:30 pm - 9:00 pm
South Central Park Downtown Winter Haven Winter Haven, Florida + Google Map

🍻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…

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November 2019

Wine Chocolate and Cheese 2019

November 21 @ 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! 🍷🍫🧀 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…

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Shop Small Business Saturday 2019

November 30 @ 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
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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