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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
+ Google Map

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

South Central Park transforms into a German biergarten as we invite you to sample over 50 craft and international beers, your favorite Bavarian food, and live music! Entrance is FREE, tickets for the beer and wine tasting will be on sale shortly.

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November 2019

Wine Chocolate and Cheese 2019

November 7 @ 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! Downtown businesses will host a wine and cheese OR a wine and chocolate pairing! Attendees will purchase a ticket and receive a map and a tasting glass to visit all of the participating locations. Live music on the street a great night to explore downtown with friends while enjoying great wine & bites. Check-in will begin promptly at 5:30PM on the southeast corner of…

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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
Free

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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