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May 2019

Bark in the Park 2019

May 3 @ 6:00 pm - 9:00 pm
South Central Park Downtown Winter Haven Winter Haven, Florida + Google Map
Free

It’s a dog day in South 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 7PM. See you there!

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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
$25

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 to begin the crawl.

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July 2019

Treasure Hunt Downtown 2019

July 21 @ 11:00 am - 2:00 pm
Chamber of Commerce, 401 Ave B NW
Winter Haven, FL 33881 United States
+ Google Map
Free

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 mini figure. Once you have spotted…

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August 2019

MSWH 24th Annual Meeting

August 7 @ 5:30 pm - 7:00 pm

The Main Street Winter Haven Board of Directors invites you to join us on August 8th, from 5:30-7pm for our 23rd Annual Meeting! Enjoy appetizers and drinks before our guest speaker and new MSWH officers are introduced. Location is TBD. If you are a current member of Main Street Winter Haven, please RSVP. If you are not a member, tickets are $25 to attend and can be purchased here.

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Ladies Night Downtown 2019

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

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.

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September 2019

Bourbon and Blues 2019

September 27 @ 8:00 am - 5:00 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
Free

Save the date: December 7th - 31st Annual Carols in the Park

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