§ Nearby · 20 min northwest of Lake Wales
Polk County's Chain of Lakes town — restaurants, lakeside bars, live music, and downtown storefronts along Central Avenue.
The town
Winter Haven is built on the Chain of Lakes — 25 interconnected lakes with canals cut between them in the 1910s. Downtown wraps around Lake Silver, Legoland sits on Lake Eloise, and Lake Howard hosts the sunset crowd. It's a 20-minute drive from Lake Wales up SR-60 or US-27.
Come for lakeside dinners, catch live music at Old Man Franks, and browse the Central Avenue food hall and downtown restaurants before heading back east.
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31 matches
Featured restaurant
Lakeside seafood bar on Lake Howard — oysters, peel-and-eat shrimp, mahi, wings, and sunset seats. Host venue for Polk County Open Mic Night on Aug 5.
Where to eat
A working list of standout kitchens and lakeside bars in Winter Haven. Call ahead — hours shift with the season.
American · Steakhouse · Seafood
Classic waterfront dining experience on Lake Shipp with docked-boat seating, steaks, and fresh seafood.
701 6th St SE, Winter Haven
(863) 293-7070
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American · Seafood
Longtime local favorite for fried seafood, burgers, and homestyle plates.
2499 Havendale Blvd NW, Winter Haven
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Steakhouse · BBQ · Happy Hour
Barbecue and smoked meats in a downtown bistro setting — ribs, brisket, craft cocktails, and a popular happy hour.
363 3rd St NW, Winter Haven
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Classic American Diner
Classic Florida drive-in famous for burgers, shakes, and homemade pies.
2030 3rd St SW, Winter Haven
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Breakfast & Lunch
Family-run cafe known for breakfast, meatloaf, pot roast, and classic American comfort plates.
1008 6th St SE, Winter Haven
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Steakhouse
Popular chain known for hand-cut steaks, ribs, and fresh-baked rolls.
300 Cypress Gardens Blvd SW, Winter Haven
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Seafood
Well-known chain for lobster, shrimp, and seafood classics.
5500 Cypress Gardens Blvd, Winter Haven
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American · Waterfront Views
Burgers and seafood with waterfront views, airport-adjacent — casual dine-in and takeout.
615 7th St SW, Winter Haven
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Italian
A go-to for special occasions and celebrations — white-tablecloth Italian in historic downtown.
231 W Central Ave, Winter Haven
(863) 293-0641
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Downtown Food Hall
A downtown food hall with multiple vendors, live music, and a full bar — relaxed outdoor venue.
308 4th St SW, Winter Haven
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American · Seafood · Lakeside
Casual lakeside dining with live music on Lake Howard — seafood, steak, and weekend bands.
1006 Lake Howard Dr SW, Winter Haven
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Steakhouse · Brazilian
Local steakhouse and Brazilian-style churrascaria with a generous salad bar.
4790 S Florida Ave, Winter Haven
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Latin American · New American
Downtown chef-driven kitchen with a rotating Latin-inflected menu, cocktails, and a strong wine list.
20 3rd St SW, Winter Haven
(863) 293-1961
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Food hall · Multiple vendors
Downtown food hall with rotating stalls — pizza, sushi, tacos, coffee, and a full bar under one roof.
302 W Central Ave, Winter Haven
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Cocktails & pints
From craft cocktail rooms on 3rd Street to a whiskey bar with a patio and the town's oldest dive — Winter Haven's bar scene runs the full range.
Craft Cocktails · Lounge
Cozy lounge known for craft cocktails, live music, and a speakeasy atmosphere.
356 3rd St NW, Winter Haven
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Tiki Bar · Waterfront · Live Music
Outdoor tiki deck overlooking the lake with live music and tropical drinks.
1004 Lake Howard Dr SW, Winter Haven
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Whiskey & Craft Cocktail Bar
A premier whiskey and bourbon bar with a welcoming atmosphere and unmatched collection.
239 3rd St SW, Winter Haven
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Sports Bar · Trivia · Live Music
Sports bar with trivia nights, live music, and plenty of screens for game day.
5688 Cypress Gardens Blvd, Winter Haven
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Local Hangout · Karaoke
A beloved community spot for drinks, games, and karaoke nights.
2995 Cypress Gardens Rd, Winter Haven
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Bar & Pool Hall
Casual sports bar with pool, burgers, wings, and cold beer.
Winter Haven
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Lakeside Dive Bar & Seafood
Lakeside seafood bar on Lake Howard — oysters, peel-and-eat shrimp, and sunset seats.
1005 Lake Howard Dr SW, Winter Haven
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Hometown Corner Bar
A local favorite in downtown with live music and a large outdoor patio.
100 3rd St SW, Winter Haven
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Craft Beer & Tap House
Self-serve taproom for beer, cider, and wine — pour your own pint by the ounce.
Winter Haven
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Breweries & taprooms
Craft breweries with biergartens and self-serve taprooms for beer, cider, and wine.
Craft brewery · Biergarten
Craft brewery with a biergarten, food trucks, and rotating house beers.
Winter Haven
4.6 ★ (320)· $10–20· Opens 12 PM
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Self-serve taproom
Self-serve taproom for beer, cider, and wine — pour your own pint by the ounce.
Winter Haven
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After dark
Late-night venues, live music rooms, comedy clubs, billiards halls, and dance floors.
Live Music Venue & Dance Bar
Winter Haven's oldest bar turned live music venue — concerts, dancing, and karaoke nights.
118 3rd St SW, Winter Haven
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Lively Lakeside Music Venue
Lakeside music venue on Lake Howard — live bands, DJs, and sunset sessions.
1005 Lake Howard Dr SW, Winter Haven
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Music Venue & Cocktail Lounge
Cocktail lounge that doubles as a live music venue with a speakeasy vibe.
356 3rd St NW, Winter Haven
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Dance Bar & Nightlife Spot
Lakeside restaurant and bar with weekend dancing, DJs, and late-night energy.
1006 Lake Howard Dr SW, Winter Haven
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Country Dance Bar & Live Music
Country saloon with line dancing, live music, and a lively weekend crowd.
Winter Haven
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