Blake Walsh

20 Best Things to Do in Winter Haven, FL

  • Published 2022/10/21

Winter Haven is a bit of a mystery wrapped in an enigma.

You’ll find it hard to describe the dynamic you’ll experience once you set foot in one of Polk County’s splendiferous cities.

Standing at 51 miles east of Tampa, Winter Haven is a rapidly growing city, with its population surging to almost 50,000 people as of 2021.

The total area of this lovely town is 25 square miles with 17 square miles of land and 8 square miles of water.

Many people are flocking here due to its dynamic terrain consisting primarily of flatland interspersed with gently rolling hills and an average elevation of 146 feet above sea level.

Winter Haven has many beautiful sites, including lakes, streams, rivers, canals, forests, rivers, and springs.

This scenic paradise takes its name from the pleasant climate endured throughout much of the year.

If you’ve never been to the charming town of Winter Haven, it bears mentioning that cooler weather is all you’ll need to enjoy the nature reserves and quaint parks around here.

Whether you’re here on vacation or for business, you’ll enjoy some great activities, like biking, wakeboarding, fishing, and more.

If you’re trying to figure out what to do while visiting Winter Haven, here are the 20 best things to do in Winter Haven, FL:

Check Out the Ultimate Holiday Destination for Kids, LEGOLAND Florida Resort

Exterior of  LEGOLAND Florida Resort

EQRoy /

LEGOLAND Florida Resort is a fun place for LEGO lovers to spend the day playing with toys.

It’s the ideal place for families looking to build memories together with their kids.

Situated 45 minutes away from both Tampa and Orlando, LEGOLAND Florida is the ultimate destination.

The park includes 50 rides and attractions based on popular LEGO products and characters and parks and gardens that feature amazing botanical wonders.

Star Wars battle made with legos at LEGOLAND Florida Resort

Ritu Manoj Jethani /

It’s a 150-acre interactive destination set in beautiful Winter Haven, where your little ones can build the world virtually brick by brick!

Lego buildings at Legoland Florida Resort in Florida

EQRoy /

And when they’re tired of doing that, they can enjoy water rides and other activities or play on interactive rides for juniors.

Just right next to the entrance of LEGOLAND Florida, LEGOLAND Hotel offers 152 LEGO-themed rooms.

You will also find the park’s lakeside resort, the LEGOLAND Beach Retreat, inside with 83 unique bungalows that offer 166 separate rooms each.

Lego Ninjago at LEGOLAND Florida Resort

Ritu Manoj Jethani /

Catch Wonderful Shows at Ritz Theatre 100 Inc

At Winter Haven’s downtown core sits the Historic Ritz Theatre.

You’ll find the performing arts theater company in 263 W Central Ave, providing movie screenings as well as stage productions.

This nearly a century-old arts management business with a local heritage first served as a venue to show vaudeville acts and silent movies.

Ritz Theatre 100 Inc originally went by the name “Williamson” but later changed to “The Ritz” due to a new owner devising a whole new concept for attracting patrons.

By the 1990s, it had gone abandoned for years even though Winter Haven residents demanded its return.

Whatever you have planned for your vacation in Winter Haven, remember that you can always catch some screen time or a stage show at The Ritz Theatre!

Tee off at Willowbrook Golf Course

Swing by 4200 State Road 544 East for a splendid test that stays true.

Willowbrook Golf Course has a well-maintained layout and offers amenities suitable for golfers of all ability levels.

The Grille is available for tee time reservations and post-game celebrations.

The range provides space for hitting some balls before your game and several practice areas you can use to master your puts on the green.

The greens at this municipal golf course roll fast and flat.

There are alligators near the course, but they won’t bother you; just don’t go looking for your lost golf balls near them.

The starter here is friendly and more than happy to assist in planning out your strategy for success.

Enjoy a Nature Walk in Winter Haven’s South Lake Howard Nature Park

Lily pads on Lake Howard

Roxymoxi /

There’s nothing like a picture-perfect, large body of water such as Lake Howard.

In 1570 Lake Howard Dr. SW, Winter Haven, you’ll find a park that’s easy to navigate and brims with sunshine.

The Park comes with three different looped pathways: one measuring a quarter-mile, two at half-mile, and a mile-long, respectively.

The scenery is absolutely fantastic, and there are plenty of good fishing spots – like the one-mile-long trail that boasts only one place to get off for passing bicyclists and pedestrians, which makes it all the more worthwhile.

It’s almost like a one-mile-long challenge!

Groves of native vegetation surround the boardwalk, where bird-watchers can observe ospreys, red-winged blackbirds, great blue herons, among other wildlife.

It also welcomes trail-weary canines, and there are paths made for your furry friend where they can sniff around at leisure.

Experience Breathtaking Wildlife at Marshall Hampton Reserve

Located in Winter Haven, Florida, the 1,173-acre Marshall Hampton Reserve offers various recreational activities and beautiful scenery.

For nature lovers, this reserve is a must-see.

It exhibits a blend of oak hammocks and hardwood forests, allowing the perfect habitat for wildlife watching and outdoor activities alike.

The terrain of this reserve best suits all kinds of native wildlife, from wandering armadillos to nesting indigo buntings.

Also on site are a kiosk and a dog-friendly trail system where you can enjoy bike riding with your pet.

The general vicinity of the reserve is Circle B Bar Reserve that has wilder flora and fauna to take in.

Marshall Hampton Reserve is home to hardwood forest wetlands, a 60-acre pond, and mesic Flatwoods and is most abundant in slash pine, live oaks, palmettos, and sweet gum.

Enjoy Jazz, Food, and Ambiance at Apple Lounge

As if you needed another reason to love Apple Lounge, they have a habit of throwing the best wing-eating competitions.

This fantastic restaurant at 803 Recker Hwy, Winter Haven, also prides itself on serving juicy half-pounder burgers and freshly fried pickles.

Gather up the family on Taco Tuesdays for a free shot with every Margarita, or enjoy an ice-cold draft beer on a hot summer day without breaking your budget.

Apple Lounge is a bar without a sport’s line score.

And despite some of its patrons smoking in front of the bar, it welcomes pool sharks and trivia fans alike to test their skills on some friendly sporting games.

And for those who love music, you’ll usually hear local bands perform here as well.

Relive the Golden Age of Aviation at Waldo Wright’s Flying Service

In 1855 US Hwy. 92, West Winter Haven, lies Waldo Wrights Flying Service, which has been the go-to place for people of all ages wanting to enjoy the exhilarating thrill of traveling via vintage biplanes.

Waldo Wright’s Flying Service offers vintage plane experiences that take you back to the ‘good ole days.’

You can relive the 1930s riding their New Standard D-25 for a barnstorming ride or the 1940s riding their Boeing Stearman N2S-3 for a more hands-on WWII adventure.

You’ll be able to experience another era all together aboard Waldo’s own Travel Air 4000 on floats!

This biplane that once flew passengers during the golden age of aviation will take you on an entirely different type of trip.

With their Travel Air E-4000 ride, you can relax and enjoy nature while still getting some personal attention from their pilot.

Dive Into Life at Winter Haven Chain of Lakes

Sunset in Winter Haven Chain of Lakes

Shannon Carnevale /

There are a lot of lakes located in Winter Haven.

In fact, nine lakes make up this 6000-acre chain.

People come here to get a taste of the fishing and boating fun.

The Chain Of Lakes is a series of lakes connected by canals that stretch from Lake Hartridge to Lake Winterset in the far Southeast part of the city limits.

Pier at Winter Haven Chain of Lakes

Noah Densmore /

Boats and shorelines provide access to the South Chain and lakes Shipp, Summit, Cannon, Hartridge, and Howard.

The North Chain is accessible via lakes Rochelle, Haines, and Conine.

You’ll see fish attractors in those areas.

Bass anglers use the technique of “flipping,” casting plastic worms around shoreline plants, such as maidencane and cattail, as well as trolling them behind piers.

Aerial view of Winter Haven Chain of Lakes

Noah Densmore /

Bowl a Strike at Cypress Lanes

If you find yourself in 2010 Dundee Rd, Winter Haven anytime soon, make sure to stop by Cypress Lanes.

This fun bowling alley has splashy effects, arcade games, and lessons, and they even have a spot for exceptional American grub.

Cypress Lanes features 40 lanes of bowling that will remind you exactly why this activity is such a staple in American culture.

The entertainment facility has a Game Zone that offers you 70 cutting-edge games to sharpen your competitive edge.

Whether this is your favorite pastime or you’re just looking for something fun to do with your friends and family, we promise that you will absolutely love coming here!

From the two-story laser tag to dining and drinks, Cypress Lanes has made itself an all-in-one entertainment facility where all ages can have fun during all seasons.

Buy an Antique Souvenir at Sherman’s Antiques

Sherman’s Antiques is a tiny little shop hiding in plain sight.

You can barely see the building from outside, but once you step into the store, you will be immediately transported back to different eras, thanks to the various items on display.

There are endless vintage treasures you can find here, such as classical dolls and rare picture frames, including one of Marilyn Monroe’s.

Sherman’s has pretty much anything that anyone could ask for related to antiques!

The antiques keep changing as they are either sold or brought in, so the various experiences will vary depending on when someone goes.

Experience Ultimate Wakeboarding With Chain of Wakes

Chain of Wakes is the ultimate experience for any watersport enthusiast!

Enjoy a prime riding location with a professional yet relaxed wakeboarding experience.

Chain Of Wakes’ MasterCraft X Star boat takes you on a 30-minute ride behind the beautiful lakefront property.

Each day begins on the water at around 8:15 am for two stand-up sessions (2 x 30 minutes or 3 x 20 minutes, depending on your preference).

During those 30 minutes, you will ride with some of their professional instructors who can help you master water tricks, such as dolphin rolls, or even show off some freestyle moves like hip tosses and slams.

Visit Woman’s Club of Winter Haven

Exterior of the Woman's Club of Winter Haven

Ebyabe, CC BY-SA 2.5, via Wikimedia Commons

The Woman’s Club of Winter Haven is a fascinating place for people interested in discovering incredible memorabilia.

Located at 660 Pope Avenue, Northwest, Winter Haven’s Woman’s Club House is on the National Register of Historic Places.

It’s under the administration of The Woman’s Civic League of Winter Haven and Vicinity, an organization whose goal is to support the local community.

Building sign of Woman's Club of Winter Haven

Ebyabe, CC BY-SA 2.5, via Wikimedia Commons

As one of Florida’s oldest active woman’s clubs, it provides a relaxing getaway where visitors can relish in beauty and history for months on end.

Not only does the building represent an amazingly preserved part of Winter Haven’s history, but it also serves as an important wedding venue.

It’s easy to see why so many couples choose to get married here at this historic mansion!

Plaque marker of the Woman's Club of Winter Haven

Ebyabe, CC BY-SA 2.5, via Wikimedia Commons

Browse Unique Items at the Village Sampler

When you first arrive at The Village Sampler, you’re greeted with a coat of arms that looks like it was plucked right out of the American Revolution.

You can tell it’s an old place, but for some reason, the inside gives off the vibes of a quaint coffee shop.

The actual building itself is much bigger than it appears on its outside.

After you walk past displays from silversmiths to sportsmen, you realize there must be at least twenty booths here run by local vendors, with everything from antique jewelry to rare books and clocks.

Looking around the store feels a lot like taking a journey home, which explains why so many people return each month.

If you need something special or are looking for a quality product at a reasonable price, a visit to The Village Sampler will be worth it.

Enjoy Mouth-Watering Cajun Creole Dishes at Tempo 1930

The first Publix was a neighborhood grocery store on 58 4th St NW in Winter Haven.

The original location now has Tempo 1930, a popular restaurant that caters to those who enjoy modern southern cuisine and seek out live jazz music, local craft cocktails, and traditional pub fare.

The restaurant is open from 11 am – 11 pm every day, except for Sunday when it opens from 12 pm to 5 pm.

It found its home in the same building as the very first Publix supermarket!

At Tempo 1930, you can savor various dishes, including their premiere Cajun Creole dishes and famous triple blt (pork belly, double bacon, buffalo cauliflower).

This particular bar has mixed drinks in high quantities – all come in different variations, so be sure to check the house specialty each day.

Feel Adventurous and Experience the Paddleboard Winter Haven

A recognized professional paddleboarding business, Paddleboard Winter Haven is located in Winter Haven, Central Florida.

Allow their qualified instructors to take you on the water and provide helpful advice to paddle boarders of all skill levels.

They provide a range of activities, including Paddlefit workouts, Yoga on the water, exclusive paddle board events, business “board” meetings, and introductory excursions.

Polk County has many paddle-boarding possibilities, whether you’re a beginner or an expert.

Paddleboard Winter Haven assists novices with their training and routines.

This pastime is a wonderful way to get some exercise and see the stunning Winter Haven Chain of Lakes.

Try Something New at World Barefoot Center

The World Barefoot Center was founded in 2009 and is situated in Winter Haven, Florida.

They take great delight in leading the field in their sport.

Three of the finest barefoot water skiers worldwide are on their squad, along with some of the best instructors in the world.

Skiers of every age and ability level, from beginners to experts, are accommodated at the World Barefoot Center.

The nicest thing about going there is the diversity of their learners, who range from absolute beginners to international champions.

All sizes, including junior to XXL, can rent barefoot wetsuits at the World Barefoot Center.

Spend the Weekend Relaxing at Cypress Campground & RV Park

Winter Haven, Florida’s Cypress Campground & RV Park, offers visitors to Central Florida an outdoor vacation experience.

Winter Haven, Florida, is the sole campsite, RV park, resort, or camping site on Cypress Gardens Boulevard.

It is bordered by various lakes, retail stores, theaters, restaurants, golf resorts, and other leisure opportunities.

The RV park is next to a Super Wal-Mart and has a private entrance accessible on foot, making it ideal for family camping.

On 19 flat acres of outdoor comfort, the park includes 200 RV camping spots, and 120 pull-through sites, many of which are big rig friendly.

They provide a wide range of facilities, such as year-round events geared toward elders, while maintaining a mix of campers and RVers.

Grab Items to Use at Marine Supply

Maritime Supply is a family-run business that provides a wide range of marine items. Their inventory is unrivaled.

They enjoy having the most pleasant and knowledgeable personnel in Winter Haven, Florida.

In addition to offering components and equipment for a once-in-a-lifetime experience, their mission is to assist customers in finding the ideal watercraft to suit their style.

They can offer you the newest and greatest maritime items to improve your enjoyment of outdoor life.

The newest advancements in boating technology are a specialty of Marine Supply.

Marine Supply is a comprehensive shop for purchases, services, and entertainment!

Relax and Attend a Lesson in Four Purls Yarn Shop

With more than 2,800 square feet of beautiful fiber, Four Purls Yarn Shop is the biggest yarn shop in Central Florida.

It is a family-run yarn store with the name “four purls” in recognition of the four kids.

You’ll discover something in their selection of premium knitting and crochet yarns, needles and hooks, accessories, books, and patterns, whether fiber arts are your pastime or your passion.

They provide a laid-back and enjoyable atmosphere for all skill levels.

Attend a lesson, relax and knit, crochet, spin, or simply be fascinated by their lovely fiber, yarns, and drifting when you drop by.

Final Thoughts

Winter Haven is a rustic city full of surprises.

The many alluring points of interest listed here bring full enjoyment to the fore during any season.

From airy museums to towering Legoland theme parks (with an array of attractions hosted within), there is something here for every being with delightfully thrilling flair!

So if you’re dropping by the city, be sure to explore these targeted spots that collectively represent the charming member of Polk County.

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