Our monthly ranking of the best happy hours in Winter Park, refreshed for August 2026. Rankings favor venues with verified specials, real menus, and strong ratings out of the 110 happy hours we track here.
Drinks: from 4p-6p $10 Signature Cocktails $8 Wine $2 off on Beer and Seltzers 04:00 PM - 06:00 PM Wednesday Happy Hour from 4p-6p $10 Signature Cocktails $8 Wine $2 off Beer & Seltzers $10 and more
View full profile →When: Daily 4PM to 7PM
Drinks: Daily from 4PM to 7PM and get 25% off all drinks (except canned beverages)
View full profile →When: 5pm - 7pm
Drinks: $8 House Wines $8 House Sparkling $3 off Spritzes & Wine Cocktails $2 off Wine Pours and Draft Beers $10 off Select Wine Bottles Hand Crafted, Wine Based Cocktails
View full profile →When: 2 - 5pm
One of Winter Park's standouts: a 4.5-star hamburger restaurant, happy hour 2 - 5pm, full menu on their profile.
View full profile →When: 4 PM - 6PM
One of Winter Park's standouts: a 4.5-star cocktail bar, happy hour 4 PM - 6PM, full menu on their profile.
View full profile →Drinks: in Town × FREE BRUSCHETTA with Purchase of a Pitcher of Sangria FRIDAY, SATURDAY & SUNDAY
View full profile →When: Monday Through Friday 4pm - 7pm
Drinks: $5 Margarita Tuesday $5 Martini Monday Monday through $5 Martini Monday $5 Margarita Tuesday $5 Martini Monday All day
View full profile →When: Thursday Lunch 11:00AM – 4:00PM
Food: Sunday -- from 11AM to 3PM BRUNCH COCKTAIL “BOGO” SPECIAL – 10
View full profile →Drinks: Specials Monday: $4 Margaritas Tuesday: $3 PINTS Hospitality Night FREE POOL 10p-cl Happy Hour prices -1 WELLS
Food: Tuesday: Hospitality Night; Friday: 5-for-$22 Corona/Corona Lt & Modelo Bkts; Sunday: Hospitality Night
View full profile →When: Mon - Fri 4:00 PM-6:00 PM
One of Winter Park's standouts: a 4.2-star american restaurant, happy hour Mon - Fri 4:00 PM-6:00 PM, full menu on their profile.
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