Top 15 Attractions and Activities in Winter Haven, Florida

Located in Polk County, the city of Winter Haven has been home to LEGOLAND Florida since 2011. This resort features three parks and occupies the historical site of Cypress Gardens, an amusement park and botanical garden established in the 1930s.

Winter Haven is accustomed to hosting visitors. A particularly notable feature of this city is the Chain of Lakes, which encompasses numerous interconnected bodies of water.

LEGOLAND is situated on Lake Eloise and has continued the longstanding tradition of offering daily water ski shows originally initiated by Cypress Gardens.

Additionally, downtown Winter Haven boasts charming 1920s-era architecture, alongside a thriving farmers’ market held every Saturday morning.

1. LEGOLAND Florida

Source: Rob Hainer / shutterstock

The world’s second-largest LEGOLAND theme park replaced the former Cypress Gardens in 2011. This 145-acre park has become the focal point of an expanding resort, which includes three primary parks as of my latest information.

Spanning 14 distinct sections, the attractions at LEGOLAND Florida are thoughtfully designed for children aged 2-12, all thematically centered around the iconic brick system.

In this context, Miniland USA features LEGO replicas of globally recognized landmarks, while DUPLO Valley offers rides and activities for toddlers.

The park has also preserved elements from Cypress Gardens, including the stunning botanical gardens that showcase a notably large Banyan tree.

Another enduring feature is the live water ski show on Lake Eloise, now themed around LEGO, complete with impressive stunt choreography.

2. LEGOLAND Florida Water Park

Upon the transformation of Cypress Gardens into LEGOLAND, the previous water park Splash Island was reimagined with a LEGO theme.

Access to LEGOLAND Florida Water Park is incorporated with admission to the main theme park. The attractions here primarily cater to children up to 12 years of age.

A recent addition is DUPLO Splash Safari, an interactive water play area designed for children six years old and younger.

Other features include a lazy river where visitors can construct their own LEGO rafts, a wave pool, the Twin Chasers raft slide, and Joker Soaker, a large interactive play zone.

3. Peppa Pig Theme Park

A dedicated theme park for the beloved children’s television character, Peppa Pig, opened at LEGOLAND Florida Resort in 2022.

This park requires a separate admission package and represents the world’s first standalone theme park for Peppa Pig, specifically designed for preschoolers.

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

A memorable highlight for young visitors is Grampy Rabbit’s Dinosaur Adventure, featuring a dinosaur train ride through a valley with smoking volcanoes, which is visually striking.

Another engaging activity is the pedal bike tour, which offers a tricycle trail meandering through a sensory-rich environment of woods and hills.

4. Downtown Winter Haven

Although small, downtown Winter Haven is vibrant and navigable on foot, featuring independent restaurants, bars, performance venues, and retail establishments.

Before the establishment of Cypress Gardens, Winter Haven experienced a period of rapid expansion followed by a decline in the late 1920s.

This historical era endowed the downtown district with multiple significant architectural structures. Noteworthy among these is the Ritz Theatre (1925), which continues to function as a performance venue and screens classic films.

The pet-friendly Winter Haven Farmers’ Market occurs every Saturday morning, come rain or shine, presenting an authentic community market brimming with fresh produce, arts and crafts, and food vendors.

Lastly, at the time of this writing, the city has launched a splash pad at Trailhead Park, providing a wonderful recreational space for families, operational year-round.

From this park, visitors can embark on a hike or biking excursion along the southern Chain of Lakes, extending to Lake Alfred.

5. Paddleboarding

In my view, the optimal way to explore Winter Haven’s Chain of Lakes and canals is by water. The city’s abundant sunshine and extensive tranquil waters create ideal conditions for paddleboarding.

Situated adjacent to Lake Howard near downtown, Paddleboard Winter Haven offers hourly and daily rentals. Various tours and experiences are also available.

The Paddle Like a Pro tour, lasting 90 minutes, provides essential knowledge for enthusiasts, while the Just the Basics tour covers fundamental skills for beginners.

Additionally, options such as Yoga on the Water or Fit Classes, featuring interval training and core strengthening exercises, are available.

For participation in any of these activities, essentials such as sunscreen, sunglasses, a hat, and water-appropriate clothing are recommended.

6. Living Lake Water Boat Cruises

For those preferring a more tranquil means of exploration, boat cruises offer an opportunity to discover the city’s lakes and waterways at a leisurely pace. Living Water provides pontoon tours that are ideal for families with young children.

Led by a local guide, participants can observe a diverse array of aquatic wildlife, including alligators, otters, and various bird species, from anhingas to herons and osprey.

Insightful anecdotes regarding Cypress Gardens can be discovered during the tours, which also include visits to the historic bridge where iconic performers once delighted guests.

Tour durations include options for one-hour and two-hour excursions, with opportunities to witness the LEGOLAND ski show from a unique viewpoint on Lake Eloise.

Other notable offerings encompass sunrise and sunset cruises, featuring the LEGOLAND fireworks display on Lake Eloise.

7. Theatre Winter Haven

It seems that Winter Haven possesses a deep appreciation for the performing arts, evident through its recognition as home to one of the premier community theaters in the United States.

Established in 1970, Theatre Winter Haven showcases a MainStage season comprised of five productions, hosted within a modern complex at Chain O’ Lakes Park, which accommodates 332 attendees in the main auditorium.

Having attended performances of Little Shop of Horrors and Hairspray, I was impressed by both the caliber of the productions and the overall state of the theatre’s presentations. Alongside the MainStage shows, SecondStage presentations and student Academy productions enrich the season.

On select Tuesdays throughout the year, audiences can enjoy tribute concerts honoring classic rock and pop music legends.

8. Cypress Gardens Water Ski Show

Cypress Gardens captured public attention with its stunning water skiing performances.

Recognized as the Water Ski Capital of the World, this attraction broke numerous records across the 20th century.

Although Cypress Gardens was integrated into LEGOLAND Florida in 2009, the renowned water ski team persists in entertaining audiences.

These performances occur on the third Saturday of each month at Lake Silver, with a prime viewing location from the recently upgraded Martin Luther King Jr Park.

The seasoned performers have decades of experience, with some team members in their 60s, serving as a nostalgic nod to a bygone era, and their ability still astounds spectators.

9. South Lake Howard Nature Park

In the southern Chain of Lakes area, Lake Howard is the largest body of water located within downtown, encapsulating over 620 acres.

The park situated on the southwest shore exemplifies all that I admire about Winter Haven. Here, mere moments away from downtown’s bustling storefronts and amenities lies a picturesque natural wetland.

A boardwalk traverses the wetlands, offering splendid views of the lake. The park attracts a rich variety of wildlife, particularly wading birds like egrets and herons.

Alligators are also plentiful, with young alligators often spotted in shallower areas near the fishing dock.

10. Auburndale Speedway

I openly admit to having a fondness for stock car racing, and my experience at the Auburndale Speedway in Winter Haven was thoroughly enjoyable.

Auburndale Speedway is a ¼-mile paved track, hosting events nearly year-round, with a brief pause during the summer from mid-June to late August.

Racing events generally occur on Saturday nights, featuring diverse classes such as Pure Stocks, Mini Stocks, Street Stocks, A-Mods, Crown Vics, Mini Cup, and Bandoleros.

For an exhilarating family experience, be sure to attend the Nights of Destruction event, scheduled for late March, which showcases two nights filled with monster trucks, demolition derbies, burnout competitions, and a thrilling figure-8 race involving school buses.

11. Chain O’ Lakes Park

For over 50 years, up until 2008, Winter Haven served as the spring training grounds for two Major League Baseball teams.

The Boston Red Sox held their spring training from 1966 to 1992, followed by the Cleveland Indians from 1993 to 2008.

Their venue was Chain O’ Lakes Park, part of an expansive recreation complex situated on Lake Lulu.

This location is also home to Theatre Winter Haven, the Rowdy Gaines Olympic Pool, and the large AdventHealth Fieldhouse and Conference Center.

Addtionally, on-site amenities include popular chains such as Starbucks, Panera Bread, and Chick-fil-A.

12. Cypress Lanes

Cypress Lanes functions as more of a family entertainment center than merely a bowling alley, having been a cherished local fixture for many years.

The establishment offers 40 bowling lanes, catering to league bowlers and walk-in customers alike. A variety of walk-in packages are advantageous for larger groups; for instance, one package I purchased included two hours of bowling along with a 14” pizza.

Complementing the bowling experience, an arcade with over 70 contemporary games is available, as well as Final Assault Laser Tag, featuring advanced vests and weaponry combined with state-of-the-art lighting effects.

13. Marshall Hampton Reserve

Source: mbarrison / Flickr

For those seeking a respite from Winter Haven’s amusement parks, a vast expanse of nature lies between the city and Lakeland to the west.

Spanning over 1,100 acres, Marshall Hampton Reserve showcases a diversity of ecosystems, including pine flatwoods, cypress dome swamps, and oak hammocks. A notable feature is a 60-acre lake.

Two primary trails offer visitors a glimpse of the reserve’s towering stands of slash pine, live oaks, palmettos, and sweet gum. Both trails are flat and accessible for families.

The Osprey Overlook Loop Trail follows the western shoreline of the lake across open terrain, while I personally preferred the Acorn Hammock Loop, which winds under a lush canopy featuring magnificent oak trees.

14. Whitehead’s Blueberry Farm

Central Florida typically experiences its blueberry season during spring, specifically from late March to early May, depending on annual conditions.

Winter Haven hosts a U-Pick farm located on the southern edge of the city, near the scenic shores of Lake Eloise.

The farm usually operates seven days a week, although it may close periodically to allow for berry ripening, so checking the website beforehand is advisable.

For those pressed for time, pre-picked berries are available for purchase at the farm stand. Additionally, picnic tables are situated beneath trees, making it an ideal spot to enjoy a packed lunch.

15. Willowbrook Golf Course

Source: willowbrook-golf.com

Water hazards are a significant feature at any golf course in Winter Haven, and the 18-hole Willowbrook Golf Course has been operational since 1967, situated on a beautiful landscape between Lake Smart and Lake Fannie.

The wildlife observation during my round was exceptional, with sandhill cranes, ibises, and numerous alligators present throughout the course.

This course presents challenges even for seasoned players, featuring tight fairways with water hazards that penalize less precise shots.

With several doglegs and multiple bunkers, there are sufficient par and birdie opportunities to maintain a positive experience.