Main Street Winter Haven
Cocktail Classic Winner
Sage Cocktail Lounge is our Inaugural Cocktail Classic Winner!
Winning the Best Cocktail Lounge, the Best Cocktail, The Espresso Martini, and the Best Bartender, Jess! Congratulations
"Thank you, MSWH, for putting on the Cocktail Classic! We were truly honored to compete alongside such incredible local talent and generations of experience.
I completely attribute these wins to our amazing staff, to Jess and Brittany for being such incredible leaders, and especially to the locals who have shown us so much grace and support over the past 14 months as we’ve continued to learn, grow, and improve.
We’re incredibly grateful for the support and proud to be part of this community. Thank you!"— Josh Pearce
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Ladies Night Self Care Social
September 10, 2026
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Oktoberfest
October 9 | 6:00-9:00 PM Main Street Winter Haven’s 19th Annual Oktoberfest...
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Wine, Chocolate, and Cheese
November 13 | 5:30-8:30 PM Main Street Winter Haven is excited to...
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Small Shop Saturday
November 28, 2026 Save the date to support!
Thank you to our outstanding Benefactors!
A special thank you to our Visionary Benefactors for 10+ years of support
Learn more about Main Street's Projects and Programs
