15 Best Things to Do in Winter Haven (FL)

Written by Bart Meeuwesen
Updated on
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In Polk County, the city of Winter Haven has been home to LEGOLAND Florida since 2011. With three parks, this resort is on the site of Cypress Gardens, an amusement park and botanical garden established in the 1930s. 

So, I think it’s fair to say that Winter Haven is used to welcoming guests to the city. A truly remarkable thing about this place is the Chain of Lakes, with dozens of interconnected bodies of water throughout the city.

LEGOLAND itself is on Lake Eloise, and has continued Cypress Gardens’ long-standing tradition of a daily water ski show.

Downtown Winter Haven also needs to be kept in mind, with lovely 1920s architecture, and a year-round farmers’ market on Saturday mornings.

1. LEGOLAND Florida

LEGOLAND FloridaSource: Rob Hainer / shutterstock

The world’s second-largest LEGOLAND theme park took over from the old Cypress Gardens in 2011. The 145-acre park has become the showpiece of a growing resort, which had three main parks when I wrote this list.

Across 14 different sections, the rides, shows and play areas at LEGOLAND Florida are carefully crafted for kids aged 2-12, all with the famous brick system as a theme.

In that spirit, Miniland USA features LEGO models of world-famous monuments and landmarks, while DUPLO Valley has rides and games for toddlers.

The park has also integrated elements from Cypress Gardens, including the gorgeous botanical gardens with a truly massive Banyan tree to check out.

Another holdover is the live action water ski show on Lake Eloise, now with a LEGO theme and awesome stunt choreography.

2. LEGOLAND Florida Water Park

When Cypress Gardens was turned into LEGOLAND, the former water park Splash Island was given a LEGO theme. 

Admission to LEGOLAND Florida Water Park is included with entry to the theme park. Again the attractions here are mainly aimed at children up to the age of 12. 

One of the recent additions is DUPLO Splash Safari, a hands-on zero-depth water playground for children aged six and under.

Elsewhere there’s a lazy river where you can build your own LEGO raft, a wave pool, the Twin Chasers raft slide, and Joker Soaker, a giant interactive play area.

3. Peppa Pig Theme Park

An entire theme park dedicated to the popular children’s TV character, Peppa Pig, opened at LEGOLAND Florida Resort in 2022. 

Requiring a separate package ticket, this is the world’s first standalone theme park for Peppa Pig, and is aimed entirely at preschoolers. 

Among the attractions is Daddy Pig’s Roller Coaster, George’s Fort, Muddy Puddles Splash Pad, and Peppa Pig’s Balloon Ride, an aerial carousel with excellent views of the park.

One of the day’s great successes for my little one was Grampy Rabbit’s Dinosaur Adventure, where you ride a dinosaur train past smoking volcanoes. It will make more sense when you see it. 

Also perfect for burning some energy is the pedal bike tour, with a tricycle trail leading through a multi-sensory environment of woods and mountains.

4. Downtown Winter Haven

Small but buzzing with life and easy to get around on foot, the downtown area on W Central Avenue is full of independent restaurants, bars, performance venues and shops.

Before the days of Cypress Gardens, Winter Haven went through a period of sudden growth followed by bust in the late 20s. 

This period furnished the downtown area with a lot of historic architecture. There are more than two dozen contributing buildings in the historic district here. A prominent one is the Ritz Theatre (1925), still serving as a performance space, and also screening classic movies.

The pet-friendly Winter Haven Farmers’ Market takes place every Saturday morning rain or shine. This is an authentic community market, loaded with fresh produce, arts and crafts, and food trucks.

Finally, when I wrote this article the city had just unveiled a splash pad downtown at Trailhead Park. This is a wonderful amenity for families and is open all year. 

Meanwhile from this park you can set off on a hike or bike ride past the southern Chain of Lakes as far as Lake Alfred.

5. Paddleboarding

As far as I’m concerned, the best way to discover Winter Haven’s Chain of Lakes and canals is on the water. The city’s ample sunshine and thousands of acres of calm water is made for a paddleboarding trip.

Set next to Lake Howard close to downtown, Paddleboard Winter Haven offers rentals by the hour or day. You can also join in on a wide range of tours and experiences.

You can pick up everything you need to know on the Paddle Like a Pro tour, which is 90 minutes long. Still, if you just want enough to get going, there’s also the Just the Basics tour. 

In addition you can sign up for Yoga on the Water or Fit Classes, involving interval training and core workouts. 

For any of these experiences, sunscreen, sunglasses, a hat, and water-friendly clothing are all essential.

6. Living Lake Water Boat Cruises

You can tour the city’s lakes and waterways in a faster and more sedate fashion on a boat cruise. Ideal for families with younger children, Living Water offers a lineup of pontoon tours.

With a local guide you’ll get up close to rich aquatic life, seeing gators, otters and profuse birdlife, from anhingas and herons to osprey. 

I was fascinated by the anecdotes about Cypress Gardens, and the tours take in the old bridge where the attraction’s famous southern belles once stood.

There are one-hour and two-hour tours, and you can also head out onto Lake Eloise to see the LEGOLAND ski show from a new angle. 

Other worthwhile options include sunrise and sunset cruises, including the LEGOLAND fireworks show on Lake Eloise.

7. Theatre Winter Haven

I reckon there’s a love of performance in Winter Haven’s veins, as the city also has one of the top community theaters in the country. 

Founded in 1970, Theatre Winter Haven puts on a MainStage season with five performances. These take place in the modern complex at Chain O’ Lakes Park, with seating for 332 in the main auditorium.

I saw Little Shop of Horrors and Hairspray, and was astonished by the quality of performances, and all-round production values. Along with the MainStage series, there are also SecondStage shows, and student Academy productions.

On selected Tuesdays throughout the year you can catch tribute concerts for classic rock and pop acts.

8. Cypress Gardens Water Ski Show

One of the things about Cypress Gardens that really caught people’s attention was the water skiing feats that took place here.

The attraction became known as the Water Ski Capital of the World, breaking dozens of records throughout the 20th century. 

Although Cypress Gardens was folded into LEGOLAND Florida in 2009, their emblematic water ski team continues to perform for the public. 

These shows take place on the third Saturday of every month at Lake Silver. You can see all the action from the newly renovated Martin Luther King Jr Park. 

The performers have been in the business for decades, and some members of the team are even in their 60s. It’s a nostalgic reminder of a different time, and I was amazed by what the team can still do.

9. South Lake Howard Nature Park

In the southern Chain of Lakes, Lake Howard is the largest in the downtown area, at more than 620 acres. 

The park on the southwest shore is a reminder of everything I like about Winter Haven. Here, within moments of downtown’s shops and amenities, is a picture-perfect natural wetlands.

A boardwalk takes you across the wetlands, and has fabulous views of the lake. The park welcomes a lot of wildlife, in particular waders like egrets and herons. 

Also here in abundance are alligators, and you’ll see young ones in the shallow areas around the fishing dock.

10. Auburndale Speedway

I don’t mind admitting that I’m a sucker for stock car racing, and had a whale of a time at this track in Winter Haven.

Auburndale Speedway is a ¼-mile paved track, with events pretty much all year, except for a summer break between mid-June and late August.

Events normally take place on Saturday nights. A few of the classes involved are Pure Stocks, Mini Stocks, Street Stocks, A-Mods, Crown Vics, Mini Cup and Bandoleros.

For a night of chaotic family fun, look out for Nights of Destruction, around late March. This event brings two nights of monster trucks, demolition derbies, burn out contests, skid cars, and a crazy figure 8 race with school buses.

11. Chain O’ Lakes Park

For more than 50 years up to 2008, Winter Haven was the spring training for two Major League Baseball teams. 

The Boston Red Sox were here from 1966 to 1992, and then the Cleveland Indians spent their preseasons in Winter Haven up from 1993 to 2008.

Their home from home was Chain O’ Lakes Park, which is still part of a large recreation complex on Lake Lulu. 

This is the venue for Theatre Winter Haven, as well as the Rowdy Gaines Olympic Pool, and the cavernous AdventHealth Fieldhouse and Conference Center. 

Also on the grounds are locations for Stabucks, Panera Bread and Chick-fil-A.

12. Cypress Lanes

More of a family entertainment center than a simple bowling alley, Cypress Lanes has been a local mainstay for decades now. 

There are 40 lanes of bowling, with plenty of space for league bowlers and walk-ins. I like the various walk-in packages, which are great value for larger groups. For instance, when I was there the Family Fun Pack gave us two hours of bowling, plus a 14” pizza.

To go with bowling, there’s an arcade with 70+ games, many of which are new. Then there’s Final Assault Laser Tag, with cutting-edge vests and guns, and integrated lighting technology.

13. Marshall Hampton Reserve

Marshall Hampton ReserveSource: mbarrison / Flickr
Marshall Hampton Reserve

If you need a break from Winter Haven’s amusement parks there’s a large expanse of nature between this city and Lakeland in the west.

On 1,100+ acres, Marshall Hampton Reserve is a medley of pine flatwoods, cypress dome swamp, and oak hammock. There’s also open water at a 60-acre lake.

There are two main trails, giving you a taste of the reserve’s large stands of slash pine, live oaks, palmettos and sweet gum. Both are flat and can be walked by families.

The Osprey Overlook Loop Trail traces the western shore of the lake, across open ground. My pick of the two was the Acorn Hammock Loop, under a dense canopy with spectacular oaks along the route.

12. Whitehead’s Blueberry Farm

Depending on the annual conditions, Central Florida’s blueberry season takes place in springtime, between late March and early May.

In Winter Haven there’s a U-Pick farm right on the southern edge of town. It’s a beautiful spot, close to the shore of Lake Eloise. 

The farm is usually open seven days a week, although it may close to allow more berries to ripen. So I’d take a look at the website before heading out.

If you’re pushed for time you can buy pre-picked berries from the stand here. There are also picnic benches under the trees, so it’s worth packing a lunch when you visit.

15. Willowbrook Golf Course

Willowbrook Golf CourseSource: willowbrook-golf.com
Willowbrook Golf Course

You can be sure that water is going to be a factor at any golf course in Winter Haven. Opened in 1967, the 18-hole Willowbrook Golf Course has a jaw-dropping location, on a mature landscape between Lake Smart and Lake Fannie.

What will stick with me about my round here is the wildlife. With so much water all around, it was no surprise to see sandhill cranes, ibises, and plenty of alligators.

This is a course that will challenge the best players. The fairways tend to be tight, with water hazards waiting to claim any shot that isn’t pinpoint accurate. 

There are several doglegs and a lot of bunkers, but enough par and birdie opportunities to keep your spirits up. 

15 Best Things to Do in Winter Haven (FL):

  • LEGOLAND Florida
  • LEGOLAND Florida Water Park
  • Peppa Pig Theme Park
  • Downtown Winter Haven
  • Paddleboarding
  • Living Lake Water Boat Cruises
  • Theatre Winter Haven
  • Cypress Gardens Water Ski Show
  • South Lake Howard Nature Park
  • Auburndale Speedway
  • Chain O' Lakes Park
  • Cypress Lanes
  • Marshall Hampton Reserve
  • Whitehead's Blueberry Farm
  • Willowbrook Golf Course