Blake Walsh

15 Free Things to Do in Winter Haven, FL

  • Published 2022/11/30

The city of Winter Haven in Central Florida is any lake lover’s paradise.

Located 51 miles from Tampa, Winter Haven may not be as big as most cities within Polk County, but you shouldn’t underestimate it.

Its quaintness, set within an All-American downtown, is a breath of fresh air.

Dubbed the Chain of Lakes City, Winter Haven is home to almost 30 lakes, all linked by a canal and offering lots of majestic sceneries.

Before it became known for its outdoor recreation, it was called Harris Corners in 1884 for its thriving fruits and vegetable industry.

After its incorporation in 1911, it saw a boost in the financial industry.

Now, it’s a hidden gem in Florida brimming with recreational sites like Legoland theme parks and vintage aircraft museums!

Below are some free things to do in Winter Haven, Florida, should you want to visit.

Go on a Nature Hike at Marshall Hampton Reserve

On Thornhill Road, a wonderful world of nature awaits your arrival.

Marshall Hampton Reserve is your best option for multi-use trails and a vast expanse of land.

Acquired in 2008, this nature reserve runs along the edge of Lake Hancock and is a local favorite because of its extraordinary collection of wildlife.

The trails run over approximately seven miles, highlighting the oak hammocks as you go further and further into the woodlands.

If you have a horse you’d like to ride around, get your free permit at the Polk County office.

The 60-acre pond also provides serene nature viewing, with the occasional bird greeting you while you’re at it.

Best of all, Marshall Hampton Reserve doesn’t require you to pay anything to visit!

Join Open Mic Night at Gram Parsons Derry Down

In downtown Winter Haven, entertainment doesn’t always come with an entrance fee.

Gram Parsons Derry Down, opened in 1964, is a historic listening venue that offers high-quality shows and events.

Back then, it was only a venue that brought together The Shilos, where Gram Parsons played.

Soon enough, the place became a powerhouse of Central Florida culture.

So, in 2014, the Derry Project opened to preserve this historical establishment and to help branch out to serve the community.

While some of Gram Parsons Derry Down’s upcoming shows need you to buy a ticket, its Open Mic Night is free.

Enjoy a night of songs and performances from veteran and beginner musicians, artists, and those who want to share their craft.

Come on over to 5th Street to experience this for yourself.

Enjoy a Free Ski Show by the Cypress Gardens Water Ski Team at Lake Silver

Who would want to turn down a free water skiing show?

Cypress Gardens Water Ski Team, formed to bring performance water skiing to Winter Haven, held its first show in 1943.

They mainly performed at Cypress Gardens Theme Park.

When the park closed in 2009, they transferred to Lake Silver, within Martin Luther King Park.

Every third Saturday of the month, this team never fails to wow the crowd with impressive stunts on the water.

From elaborate costumes to various acts and events, you’ll find no dull moment when you sit with the crowd alongside your family.

If these shows are your cup of tea, you can watch the Cypress Gardens Water Ski Team on South Lake Silver Drive.

Learn Local History at the Museum of Winter Haven History

Winter Haven’s history is one worth studying and learning.

You can do this at the Museum of Winter Haven History.

This non-profit museum details the past and culture of Winter Haven before it became a modern city.

It hosts a diverse set of artifacts and memorabilia showcasing the lifestyle of townsfolk back in the day.

View photographs, signages, and even costumes within glass-enclosed displays.

You might even catch a special themed exhibition if you come by at the right time.

Let the Museum of Winter Haven History jog your memories or help you create new ones!

This museum is free and open to the public on Pop Avenue Northwest.

Rest by the Shade at South Lake Howard Nature Park

Winter Haven’s list of natural attractions appeals to everyone.

South Lake Howard Nature Park’s appeal is its 1,000-foot boardwalk.

Walking down this boardwalk shows you the wildlife in the area and Lake Howard, also a part of the Chain of Lakes within the city.

This park on South Lake Howard Drive also features a one-mile looped trail that you can take.

Bring your bike or rollerblades for a more immersive journey along the paved pathways.

South Lake Howard Nature Park also has an observation pier you can spend your afternoon in.

This place can be your nature escapade whenever you’re in Winter Haven.

Practice Your Skateboarding Skills at the Winter Haven Skate Park

Are you a fan of extreme sports?

Then, you shouldn’t miss the Winter Haven Skate Park when you travel to this city.

This unsupervised skate park, part of Martin Luther King Jr. Park, is a well-rounded facility extending to over 17,500 feet.

Its facility tapers into two parts: a flow bowl and a street course that runs in a linear movement.

To mark the natural topography of Winter Haven and the area overlooking Lake Silver, the linear street course comes in two primary levels shaped into it.

Whether you are into bicycling or skates and scooters, you have a place in this outdoor venue.

Winter Haven Skate Park is on South Lake Silver Drive, should you visit.

Play with Your Family at Simmers-Young Park

Simmers-Young Park on American Spirit Road is a multipurpose park with 12 fields.

Spanning over 200 acres, this park is home to many soccer and cricket matches.

With at least a 250-seating capacity, it’s easily a favorite among athletes and sports lovers looking for a venue to practice or host friendly competitions.

There’s also a playground for the kids and a pavilion area for relaxing and enjoying the view.

If you’re also looking for a park that would cater to your pet’s needs, Simmers-Young Park is the park for you.

It has a dog area onsite for your pet’s enjoyment.

Admire the Lake Scenery at Martin Luther King, Jr. Park

Martin Luther King, Jr. Park is a well-known park housing various amenities and facilities for everyone.

The serene lake within the vicinity sometimes hosts water skiing shows of the highest quality for free!

If you prefer to stay outside, there’s a path that runs across the lake that you can exercise around.

Plan a picnic with your loved ones and enjoy the peace this park brings.

Everywhere you hang out at Martin Luther King, Jr. Park on South Lake Silver Drive, you should enjoy it.

Have Fun at the Splash Pad at Chain of Lakes Downtown Trailhead Park

Are you planning to spend your leisure time with your loved ones, especially kids?

Take them to Chain of Lakes Downtown Trailhead Park.

This trail park is a transportation-themed park with picnic areas and a play area for the kids.

Its centerpiece is the splash pad, where your kids can enjoy a refreshing time after exploring the city.

This place is also ideal for some reflection and meditation.

Make room in your itinerary for Chain of Lakes Downtown Trailhead Park, located on 4th Street.

Wander the Trails at Lake Hartridge Nature Park

Unleash the outdoorsy version of yourself when walking down Lake Hartridge Nature Park trails.

This park on Havendale Boulevard offers recreational opportunities for those traveling alone or with a group.

Stand by the picnic pavilion and shelter as you admire the scenery from afar.

Its one-third-mile paved trail is also a sanctuary for wildlife lovers looking to study more animal species while having fun.

Other amenities include a playground, a fishing pier, and a boat ramp.

Spend time with nature at Lake Hartridge Nature Park, your next stop on your Winter Haven exploration.

Other Things to Do Nearby

Have you finally gone through each of the spots above?

Don’t worry, for there are more free things to do nearby Winter Haven.

Enjoy the Illusion at Spook Hill

Welcome arch of Spook Hill

JennLShoots /

Spook Hill in Lake Wales, Florida, is a tourist spot you shouldn’t miss for the ultimate Florida experience.

The drive to Lake Wales only takes only 23 minutes from Winter Haven.

This stop is a gravity hill or an optical illusion.

When driving past this hill, prepare to roll upward in neutral gear.

The road of Spook Hill

Ebyabe, CC BY-SA 3.0, via Wikimedia Commons

It has also inspired a spooky legend involving an Indian tribe, a warrior chief, and a giant gator.

Spook Hill is on North Wales Drive.

Spot Wildlife at Circle B Bar Reserve

Osprey at Circle B Bar Reserve

Peter Pasterczyk /

Located on Winter Lake Road, Circle B Bar Reserve brings you that once-in-a-lifetime nature preserves experience.

Spanning 1,267 acres, this reserve also boasts a diverse set of ecosystems.

Previously a cattle ranch, Circle B Bar Reserve now also features a variety of trails for your hiking preferences.

Don’t forget to bring your camera with you and capture the essence of nature all around you at this site.

Great heron at Circle B Bar Reserve

Julie rubacha /

Look out for wildlife, like gray foxes, squirrels, and other unique reptile species.

Most importantly, be wary of alligators on the lake.

Circle B Bar Reserve is in Lakeland, 16 minutes from Winter Haven.

An alligator at Circle B Bar Reserve

Terry Kelly /

Bring Your Kids to Mackay Gardens and Lakeside Preserve

Do you need to go on a family outing outside of Winter Haven but are unsure where to go?

Mackay Gardens and Lakeside Preserve is a family-friendly spot that’s completely free!

This historical site was purchased in 2004 and is also a go-to platform for celebrating birthdays or hosting corporate programs.

If you’ve got the time, stroll along the hiking and fitness trails alone or with a loved one and make it a challenge for the both of you.

There’s also a playground to satiate your kid’s outdoor curiosity.

The whole family is a part of the fun at Mackay Gardens and Lakeside Preserve!

You only need to drive 11 minutes from downtown Winter Haven to reach this park in Lakeland.

Admire the Shrubs and Flowers at Hollis Garden

Scenic view of Hollis Garden

Sean Pavone /

In the neighboring city of Lakeside, a floral paradise awaits you.

Hollis Garden is a botanical garden that helps bring back your love for art and floriography.

With its neoclassical structure and public art displays, it’s easily a refuge for those seeking to admire the beauty of nature.

Close view of a flower at Hollis Garden

Leodidthis /

Spanning 1.2 acres, the park has various blooms, including native trees and ornamental shrubbery.

Savor the atmosphere of Hollis Garden while you take a few photos here and there.

You can find this lovely garden escapade at Lake Mirror Park, approximately 24 minutes from Winter Haven.

The grounds of Hollis Garden

AHPix /

Check Out the Exhibitions at the Polk Museum of Art

Exterior of The Polk Museum of Art

Ebyabe, CC BY-SA 4.0, via Wikimedia Commons

Are you looking for art inspiration?

Worry no more!

The Polk Museum of Art has your back.

You don’t have to pay anything to get the art experience you’ve sought.

Founded in 1966, it’s accredited by the American Alliance of Museums.

Entrance to The Polk Museum of Art

Ebyabe, CC BY-SA 2.5, via Wikimedia Commons

Learn from the variety of artworks displayed on the walls of this museum.

Student galleries are also available.

Acquaint yourself with modern contemporary art, Asian art, Ancient American art, and more!

Head to East Palmetto Street in Lakeland, only a half-hour drive from Winter Haven.

Building sign of The Polk Museum of Art

Ebyabe, CC BY-SA 2.5, via Wikimedia Commons

Final Thoughts

Winter Haven’s list of nature preserves, parks, and trails makes this city a must-visit destination.

If you’re planning to go solo or with a group, various activities await you and your loved ones!

Which free things to do in Winter Haven, Florida, are you planning to enjoy?

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