Oktoberfest comes to Winter Haven with the cold. The beer halls handle the loud nights with live music, giant steins and dancing, and lederhosen stay optional. The communal tables carry the quiet ones, bratwurst and pretzels arriving steadily with a band playing somewhere in the corner. Or a good beer with friends and an early night home. Explore Oktoberfest 2026 events and parties around Winter Haven, compare the dates, and book your tickets before they sell out.
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Fri, Oct 9Downtown Winter Haven Historic District
Main Street Winter Haven's 19th Annual Oktoberfest presented will kick off October 9, at 6:00 PM in Central Park, Downtown Winter Haven. We will have over 30 German, American, and Craft beers to taste! Buy a tasting ticket and sample as many of the beers
TastingLive music
Get the look
Outfits, steins and party kit for the season. Check delivery dates before you order.
Links go to Amazon. As an Amazon Associate, AllEvents earns from qualifying purchases.
Dirndl dressBodice, blouse, skirt and apronShop on Amazon 
Men's lederhosenLeather shorts, braces and allShop on Amazon 
Alpine hatGreen felt, with the featherShop on Amazon 
Trachten suspendersThe look for less, over any checked shirtShop on Amazon 
Lidded beer steinCeramic, with a pewter lidShop on Amazon 
Das Boot glassThe boot-shaped party glassShop on Amazon 
Hammerschlagen gameA stump, nails, a hammer: first nail flush winsShop on Amazon 
Bavarian flagBlue-and-white diamonds for the yardShop on Amazon 
Pretzel saltCoarse salt for homemade BreznShop on Amazon 
Baby lederhosenFor the smallest guestShop on Amazon 
Hot-dog dog costumeFor the dachshund racesShop on Amazon Nearby
Worth the trip from Winter Haven, soonest first.
Sat, Oct 3German American Society of Central Florida, Casselberry
$8.55 – $106.20Live musicFamily-friendly
Sat, Oct 3German-American Society, Pinellas Park
$14.64Live music
Fri, Oct 9N Avalon Park Blvd, Orlando, FL 32828, United States, Bithlo
Family-friendly
Sat, Oct 1014501 S Orange Blossom Trl, Hunters Creek
Family-friendly
Sat, Oct 17Yuengling Draft Haus & Kitchen, Tampa
FreeLive music
Sat, Oct 24German American Society of Central Florida, Casselberry
$8.55 – $106.20Family-friendly
Asked and answered
Oktoberfest events in Winter Haven run from Oct 9 to Oct 9, 2026: 1 event.
Nothing is listed in Winter Haven itself for Oct 2 – Oct 4, but 3 events are on nearby, in Tampa, Casselberry and Pinellas Park.
Yes: 9 more events are listed within reach of Winter Haven, in Tampa, Casselberry, Pinellas Park and Bithlo and more. The soonest is 6th Annual Mactoberfest! in Tampa, on Oct 3–4.
Munich's Oktoberfest runs from September 19 to October 4, 2026, 16 days on the Theresienwiese. It is on now: today is day 14.
Worth the trip
Where the season is the whole city's business, from Munich's meadow to a Bavarian village in the Cascades.
MunichThe original, since 1810
CincinnatiOktoberfest Zinzinnati
KitchenerCanada's biggest
La Crosse, WIOktoberfest USA
Frankenmuth, MIMichigan's Little Bavaria
Leavenworth, WAA Bavarian mountain village
Fredericksburg, TXHill Country's German town
New Ulm, MNSettled by Germans in 1854
DenverDenver Oktoberfest, since 1969
MilwaukeeBrew City's German roots
ChicagoStreet fests all season
New YorkStone Street and the beer hallsKeep exploring
