Happy Hour
The Attic Door
28 W Plant Street, Winter Garden, FL 34787
Tue–Thu · opening at 4:30 PM–6 PM
- Miller Lite — $5
- Yuengling — $5
- Corona — $5
Needs confirmation · 2026-09-23
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Find your next happy spot
Downtown Winter Garden happy hours & drink specials
Compare supported specials in Downtown Winter Garden, including prices, schedules and restrictions. Check each venue page for its sources and last verification date.
9 venues with drink specials · 5 with food-only specials.
Filter Downtown Winter Garden deals by time or priceHappy hours & drink specials
Drink Specials
Crooked Can Brewing Company
426 W Plant St, Winter Garden, FL 34787
Monday · exact hours unconfirmed
- Draft beer for eligible guests — 30% off
Partially confirmed · 2026-09-24
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Happy Hour
The Hangry Bison — Winter Garden
250 W Plant St, Winter Garden, FL 34787
Mon–Fri · 3–6 PM
- Hangry Hour drinks — From $5
Partially confirmed · 2026-09-23
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Happy Hour
Harlow Grove
186 S Main Street, Winter Garden, FL 34787
Mon–Fri · 4–6 PM
- Short Rib Empanada — $9
- Truffle Fries — $8
- Goat Cheese Croquettes — $15
Venue confirmed · 2026-10-16
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Mangoni Italian Market Pizza
251 Tremaine St, Winter Garden, FL 34787
Schedule conflict · call before visiting
- Draft beer — $5
- Mimosa — $6
- Wine by the glass — $6
Conflicting sources · 2026-09-23
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Matthew’s Steakhouse
360 W Plant St #102, Winter Garden, FL 34787
Tue–Sun · 3–5 PM
- Filet mignon sandwich — $18
- Whipped ricotta & beet crostini — $12
- Artisan cheese pairings — $14
Official source checked · 2026-09-23
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Spoleto Italian Kitchen — Winter Garden
21 S Main Street, Winter Garden, FL 34787
Mon–Fri · 3–5 PM
- Beer — 50% off
- Wine — 50% off
- Select pizzas — $3 off
Official source checked · 2026-09-23
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Urban on Plant Kitchen & Bar
132 W Plant Street, Winter Garden, FL 34787
Reported Mon–Fri · 3:30–6:30 PM; confirm
- Specialty cocktails — Reported $3 off
- Wine by the glass — Reported $2 off
- Draft or bottled beer — Reported $1 off
Needs confirmation · 2026-09-23
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Happy Hour
The Whole Enchilada — Winter Garden
129 W Plant St, Winter Garden, FL 34787
Tuesday · all day
- Taco combos — Special pricing; amount not supplied
- Classic margaritas — $8.99
- Red Hot Silly Peppers cocktail — $10
Venue confirmed · 2026-10-12
See all hours, deals & restrictions →Food-only specials
These venues have qualifying food deals; a drink special is not confirmed.
Food Specials
AJ's Pizza Joint
42 W Plant St, Winter Garden, FL 34787
Monday-Friday, 11 AM-3 PM
- Two NY-style slices + fountain drink — $8.99 / bundle
- Two NY-style slices + AJ's Lager — $10.99 / bundle
Official source checked · 2026-09-24
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Happy Hour
Bruno’s Oysters
426 W Plant St, Winter Garden, FL 34787
Wednesday · happy-hour times unconfirmed
- Happy-hour oysters — $2
Partially confirmed · 2026-09-23
See all hours, deals & restrictions →Food Specials
Harrell's Hot Dogs + Cold Cones
54 W Plant St, Winter Garden, FL 34787
Wednesday-Friday; exact hours unconfirmed
- All-beef hot dog, 3 toppings, fries + fountain beverage — $12.99 / bundle
Partially confirmed · 2026-09-24
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The Tasting Room at Chef’s Table
99 W Plant Street, Winter Garden, FL 34787
Mon–Fri · 4–6 PM
- Cup of soup — Price unconfirmed
- Duck fat fries — Price unconfirmed
- Roasted bell pepper dip — Price unconfirmed
Partially confirmed · 2026-09-23
See all hours, deals & restrictions →Food Specials
Thai Blossom
99 W Plant St, Winter Garden, FL 34787
Mon–Fri · 11 AM–2:30 PM last seating
- Pad Thai lunch · base price — $13.49
- Teriyaki lunch · base price — $13.49
- Broccoli lunch · base price — $13.49
Official source checked · 2026-09-23
See all hours, deals & restrictions →Other listings to check
These listings have other selections or still need supported offer details. Check their venue pages before planning a visit.