10 Best Things To Do In Winter Haven, Florida - Updated 2020

1. Visit the iconic Legoland resort to have an exhilarating day with your children

An iconic attraction of Winter Haven is its massive Legoland theme park. From the water park to the Lego rollercoasters, one can be sure to indulge in summer fun here. To enjoy the park to the fullest, we recommend staying at the onsite beach resort, which looks like it’s built out of Legos!

The second day of stay even includes a free ticket for maximum savings. Otherwise, you can opt to lodge at the Legoland hotel, with Lego-inspired rooms. While the children play, you can wind down at the heated pool and bar for a quick summer drink. Rides usually have relatively short wait times of less than 20 minutes, so don’t worry about wasting time queuing! They are all Lego-inspired and a must-do for any young Lego fan.

Legoland Florida

Address: 1 Legoland Way, 33884 Winter Haven, FL

Website: Legoland Florida

2. Bowl a strike at Cypress Lanes

Head to Cypress Lanes for some indoor entertainment. This bowling alley offers hourly lane rentals and group packages, so be sure to bring your friends and family along for some good, clean fun! In between throwing doubles and cheering for your team, you can munch on delicious snacks from the on-site bar. Whether you’re looking to compete or staying for the food, this vibrant establishment will not disappoint. They even offer party planning services to help you organize bachelor or bachelorette parties, birthday parties, and fundraisers.

Cypress Lanes

Address: 2010 Dundee Rd, Winter Haven, FL 33884, United States

Website: Cypress Lanes

Opening hours: Mon - Fri: 9am - 12:30am; Sat: 9am - 1:30am; Sun: 9am - 10pm

Price: 20 - 25 USD

3. Explore Floridian wildlife and fish in a chain of lakes

Fancy a rustic fishing trip in Pol County? Why not head over to the local lakes where fishing and boating are abundant? Located within the city, nine lakes compose this 2,400-hectare (6,000-acre) chain where you can fish and boat in the area with locals.

A tip for you: bass anglers achieve success by “flipping” plastic worms around shoreline plants such as cattail and maiden cane, as well as docks! Some popular species include the largemouth bass and the bluegill, so keep an eye out for them! After fishing, we also recommend hiking or biking the nearby Chain of Lakes trail, where you can overlook the rivers in either the northern chain or southern chain. The local Marine Supply Boating Centre is a family-owned boat dealer offering engine parts, repairs, and rentals, plus fishing supplies. So do support local businesses and don’t worry about procuring your hooks and boats!

Winter Haven Chain of Lakes

Address: 684-, 898 4th St NW, 33881 Winter Haven, FL

Facebook: Winter Haven Chain of Lakes

4. Experience adventure by signing on for beginner wake-boarding lessons

Photo is only for illustrative purposes

Florida in the summer presents an exhilarating opportunity for those who want to get in the water: wake-boarding lessons! A review from their Facebook page reads: “(Owners) Stew and Sam run a wake school like no other. The location, coaching, and wake are all world class. Winterset Lake is spring fed which means it’s the most blue lake on all of the 16 Chain of Lakes. Stew and Sam have competed and judged for Team GB at world level which means they will fast-track your riding ability. You’ll also have a lot of fun on or off the water within Winter Haven’s hot spots. So if you want to wake surf, wake-board or other, Chain of Wakes is the bomb.”

With the promise of experienced coaches and a lovely location, wakeboarding lessons sound ideal while you’re here in Winter Haven! Other forms of water sports are also available, such as tube rides and water ski! So should you already be experienced in wakeboarding, feel free to try out any of these adrenaline-filled activities.

Chain of Wakes

Address: 6380 Cypress Gardens Blvd, 33884 Winter Haven, FL

Facebook: Chain of Wakes

5. Browse through antiques from the 50s and 60s in this quaint shop

Photo is only for illustrative purposes

Sherman’s Antiques is a small nondescript shop from the outside. But within the store, one can be transported back into an array of timelines, from vintage dolls to a framed picture of Marilyn Monroe. This store is packed full of vintage treasures of all kinds of jewelry, dishes, and dolls and every type of memorabilia you can think of, all beautifully displayed from floor to ceiling. You could spend several hours here browsing through the little quirks! The antiques change frequently too, with customers purchasing and new stock coming in, so your experience is a dynamic one too.

Sherman' Antiques

Address: 1103 6th St NW, 33881 Winter Haven, FL

Website: Sherman’ Antiques

6. Take a hike through the Marshall Hampton Reserve

The Marshall Hampton reserve is a slightly more difficult route and thereby might not be suitable for families with small children. Nonetheless, it remains a scenic trail for those who are more athletic. The trail has three walking loops. Palmetto is the closest to the entrance and is a relatively easy walk.

The Osprey Overlook Loop is mostly on a berm around a large pond. A favorite spot for water fowl, be sure to keep your eyes peeled for some great photographs. Although, be careful here as the berm has a lot of uneven ground and holes.

Continuing on, the Acorn Loop is a nice walk through an oak hammock. There are some low areas that could get soggy if there has been rain, so take care not to slip. There is a picnic table at the entrance if you want to grab some quick packed lunch, but no restrooms so remember to go before you hike.

Marshall Hampton Reserve

Address: 3115 Thornhill Rd, 33880 Winter Haven, FL

7. Spend a relaxing afternoon trailing through the displays at the Village Sampler

Photo is only for illustrative purposes

The owners of this antique shop are warm and hospitable, making your time at the shop highly comfortable and homely. So do not feel afraid of spending some time here browsing through local history and knickknacks! You might even purchase one that catches your fancy. The key feature of the store is the Distinctive Dealer Displays selling antiques, retro, vintage, handicrafts and more and would be a wonderful attraction for those with a niche in treasure hunting and thrift shops.

The Village Sampler

Address: 155 Avenue B, SW, 33880 Winter Haven, Florida

Facebook: The Village Sampler

Things to do near Winter Haven

8. Admire vintage aircraft preciously restored in the Fantasy of Flight

The world’s only museum dedicated to showcasing the history of flight, the Fantasy of Flight places a focus on the pioneering days of early flight, World War I, World War II and beyond. Most of owner Kermit Weeks’ aircraft are airworthy and may still be seen flying from one of the facility’s grass runways or its seaplane runway. In fact, Fantasy of Flight fields more airworthy aircraft than the air forces of Austria, Cuba, Denmark, Kuwait, Portugal or South Africa. Isn’t the variety and sheer history of the collections a sight to see?

Also, check out the immersion environments in the museum, where you can be transported back into a World War II aircraft or feel the sensation of flight. From the lobby, visitors can enter the interior of a World War II-era Douglas C-47 Skytrain, complete with lighting and sound effects as if the aircraft were conducting paratrooper operations. Guests pass a seated paratrooper in full kit and move forward toward the Jumpmaster figure standing at the open side hatch.

Over the hatch blinks a red “ready” light which switches to a green “jump” light as the guest approaches the hatch. Through the hatch is the entry to the attraction. Other immersion environments include a “sensation of flight” simulator, followed by a celebration of the early days of flight.

Then, a passage covered by heavy shrapnel-resistant curtains leads visitors into a full-scale representation of the trench warfare of World War I, complete with aircraft overhead. It was, in part, due to the development of aerial warfare that trench fighting became obsolete. The experience is surreal and exciting, so we highly recommend spending some time immersing yourself in the flight experience through the ages.

Fantasy of Flight

Address: 1400 Broadway Blvd SE, 33868 Polk City, FL

Website: Fantasy of Flight

9. Get a movie experience like no other at the 1928 Polk Theatre, where the grand and lavish layout will amaze you

The Polk Theatre is a beautiful amalgamation of local history and modern film. Despite being a traditional landmark in the area since 1928, the theater still runs new film releases and is extremely lively in the local community. The theater itself has been placed on the National Register of Historic Places by the US Department of the Interior, confirming its cultural and historical importance in Winter Haven. If you are visiting soon, we recommend catching their upcoming summer family classics showing, with oldies such as the Wizard of Oz and Mary Poppins. The interior of the theater is classic and grand, making for an unforgettable film experience.

Polk Theatre

Address: 121 South Florida Avenue, 33801 Lakeland, Florida

Website: Polk Theatre

10. Stuff yourself with barbecue at the Lakeland Pigfest in January every year

Editor's Note: There's no photo available at the time of writing

In the month of January every year, Winter Haven hosts the Lakeland Pigfest, one of the largest barbecue competitions in the southeast and the largest KCBS sanctioned event in Florida. The 2017 Pigfest featured 150 competition barbecue teams during a weekend of good food, good friends, and good tunes to benefit Lakeland-area charities. Your visit will also help the community, as, since 1997, the Lakeland Pigfest has generated over 2 million dollars in charitable donations that have been disbursed to the Lakeland Community through various community partnerships. Admission is free of charge, so all you need is a good appetite and a few bucks to spare for hearty barbecue and music! Stop by a Pig Bucks booth (located near the entrance and various locations throughout) and exchange your cash for Pig Bucks, the official currency of the Lakeland Pigfest.

Lakeland Pigfest

Address: 4175 Medulla Rd, 33811 Lakeland, FL

Website: Lakeland Pigfest

Visit Winter Haven, a homely Floridian city

Winter Haven is a city full of its own charms, from antique aircraft museums to gigantic Legoland theme parks. There is simply something for everybody in the family. If you’re dropping by the city, be sure to explore the attractions listed for the full rustic charm of Polk County!