14 Best Things to Do in Winter Springs (FL)

Written by Bart Meeuwesen
Updated on
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This city in Central Florida has the only piece of developed shoreline on Lake Jesup. That 16,000-acre body of water is thought to be home to more than 10,000 alligators.

On the shores you can hike in ancient cypress forest, with trees dating back 2,000 years. Local stables will take you on horseback treks, or you can take a seat on an airboat and zip across the lake to see its gators and marvelous birdlife. 

From live music to the Scottish Highland Games, there’s something exciting going on all year at Central Winds Park by Lake Jesup. I’m not lying when I say that Winter Springs is a city that knows how to have fun.

1. Central Winds Park

Central Winds ParkSource: kellyv / Flickr
Central Winds Park

The setting for many of Winter Springs’ annual events is this beautifully tended park on the shore of Lake Jesup by the Cross Seminole Trail. 

With baseball fields, basketball courts, a fishing pier, it’s easy to see why Central Winds Park is so popular. For passive recreation there are covered pavilions, picnic areas, a dog park, and playgrounds for the little ones.

One annual shindig not mentioned in my article is the 4th of July, and Winter Springs always puts on a great fireworks show here. 

On the northwest side, the park also has a nature preserve leading down to the lakeshore. Lake Jesup is renowned for its gators, and a walk along the nature trail is an eye-opening experience. I saw a couple of big ones hiding among the bald cypresses on the shore.

2. Cross Seminole Trail

Winter Springs is near the north terminus of a 23-mile trail, wriggling through Orlando’s northern suburbs on former railroad rights of way.

If you’re like me and like exploring places by bike, this trail opens up a big swath of Central Florida. In the south the path connects to the six-mile Cady Way Trail through some of Orange County.

In Lake Mary in the north you can use it to get onto the Seminole-Wekiva Trail, continuing for another 14 miles into Seminole County along the corridor of the old Orange Belt Railway.

Locally the Black Hammock Trailhead has a parking area and restroom. From here you can ride to Central Winds Park or continue on to Spring Hammock Preserve, with its stands of ancient cypress trees.

3. Spring Hammock Preserve

Heading northwest, the Cross Seminole Trail takes you into this 1,500-acre property on the west shore of Lake Jesup.

One of the many things I adore about Spring Hammock Preserve is its botany. Growing here is what is believed to be the largest stand of tulip poplars in the state. 

There’s also a rare species of fern, and some of Central Florida’s oldest and largest cypress trees.

In the past there was a boardwalk that took you all the way through the swampy cypress hammock to the shore of Lake Jesup. This was awaiting repairs when I came. 

Adjoining the preserve to the west is Big Tree Park, which is home to Lady Liberty, a cypress dating back 2,000 years and standing 90 feet tall.

4. Black Hammock Airboat Rides

A hair-raising fact I learned recently about Lake Jesus is that it’s believed to be the most alligator-infested lake in the United States.

At the last estimate there were thought to be as many as 13,000 gators live on this 16,000-acre body of water.

So while a swim might be out of the question, this is an excellent place to see native Floridian animals in the wild. By the shore, a few minutes from Winter Springs, the Black Hammock offers Coast Guard-certified airboat rides on a fleet of four different vessels.

Gators are guaranteed, but you’re also bound to see turtles and breathtaking birdlife, including bald eagles and osprey. Bird Island in the middle of the lake harbors the largest colony of wading birds in Seminole County.

Back on dry land you can try southern specialties like fried catfish and gator tail at the restaurant, and check out some exotic birds in the aviary.

5. Bear Creek Nature Trail

For a small taste of the spectacular nature all around Winter Springs, you can escape to this short trail along Bear Creek on the east side of the city.

After a few steps Winter Springs’ suburbs will be a distant memory. The trail extends for almost a mile, with palms, live oaks and magnificent old-growth cypress trees by the path.

You’ll cross the creek on a couple of little footbridges, and there are picnic tables here if you want to bring a bite.

Like almost everywhere in the Winter Springs area, gators are part of the experience. An enormous one, estimated to be five feet long, is known to live in these woods. So my common sense advice is to take extra care if you’re here with children or dogs.

6. Hidden Palms Ranch

If you want to see more of the untouched wilderness around Lake Jesup, I’d point you towards this horseback-riding center on the north shore.

Hidden Palms Ranch offers trail rides into the Lake Jesup Conservation Area. This property is made up of deep wooded hammocks and floodplain wetlands.

Around May, masses of shorebirds stop here during their spring migration. At any time of year, you’re likely to see hundreds of American white pelicans by the water.

In the woods, birds of prey like bald eagles, osprey and hawks can be spotted on the branches. Trail rides last about 90 minutes and are available for groups of up to five.

My ideal time to come is definitely late summer when the landscape turns yellow with the blooms of thousands of wild sunflowers.

7. Museum of Seminole County History

No more than five minutes away in Sanford, there’s an informative history museum for the entire area. 

This attraction is in two buildings, the older of which dates back to 1926. The Old Folks Home was established as a place for destitute older people to stay, and then became the offices for the County Agricultural and the Home Demonstration Agent in the 1960s. 

Exhibits cover a great deal of topics, from the Native Americans of Central Florida to early forts, 19th-century life, and the development of agriculture and industry. I spent quite a while reading up on the history of the county’s fern-growing business. 

One neat display for kids is a table with lots of things they can handle, including fossils and a gator skull.

8. Trotwood Park

Another place where you can enjoy the outdoors in Winter Springs, this spacious neighborhood park has no lack of recreation amenities. For sports you’ve got a basketball court, tennis court, and a baseball diamond.

The big story for parents like me with younger children is the splash pad. Surrounded by stately live oaks, this is a wonderful facility, and has always been packed with children when we’ve visited.

There’s a lot of shade at the splash pad, and even more at the children’s playground, which has tree cover accompanied by shade sails.

Trotwood Park also has a pair of lakes. Lake Maria in the south has a fishing pier. Standing here you should see turtles and wading birds like ibises.

9. Scottish Highland Games

Scottish Highland GamesSource: Central Florida Scottish Highland Games / Facebook
Scottish Highland Games

Taking place over two days in mid-January, Winter Springs’ Scottish Highland Games is a time-honored event, first held in the 1970s. 

Organized by the Scottish-American Society of Central Florida, this is a celebration of all things Scottish, promoting the region’s strong Gaelic and Celtic heritage.

Tropical Central Winds Park may feel a long way from the Highlands’ heather and pines, but still becomes a piece of Scotland for two days every January.

For food and drink, there’s whiskey tasting, haggis, Scotch eggs, fish & chips, shortbread and—my favorite—scones. 

You can also browse a roster of vendors selling traditional Celtic crafts. Best of all for me were the demonstrations, with everything from sheepherding to bagpiping and Highland dancing.

Naturally the spotlight is on the games themselves, with heavy athletics events, from the caber toss to the stone put.

10. Oviedo Mall

On Winter Springs’ southeastern boundary, this mall opened in 1998 and has close to 100 stores. Oviedo Mall has suffered a little in the last decade, losing two of its anchors.

All the same it’s a convenient local shopping and entertainment option. A few of the national retailers here when I came were B. Dalton, GameStop, Dillard’s and Claire’s.

These are accompanied by a lot of local shops and service businesses. District Eat and Play is a lively dining/entertainment center concept for adults, with an arcade, pinball machines, bowling and escape rooms. 

Another hotspot is the 22-screen Regal Oviedo Mall, with stadium seating and a lot of classic films to go with the first-run movies.

11. Winter Springs Festival of the Arts

Winter Springs Festival Of The ArtsSource: Winter Springs Festival of the Arts / Facebook
Winter Springs Festival Of The Arts

In mid-October, there’s no better way to get your fill of mild sun and lovely art than spending time at the Winter Springs Festival of the Arts.

It’s held at the Winter Springs Town Center and had been going strong for more than 10 years when I went to press. 

Local, regional, and national artists will be on hand displaying their creations. The festival has gained quite a reputation for its tasty food and drink options too, with local craft beer.

There’s also live entertainment every year, as well as a kids’ crafts area where youngsters can explore their creative talents.

12. Winter Springs Hometown Harvest

Winter Springs Hometown HarvestSource: FestivalNet.com / Facebook
Winter Springs Hometown Harvest

By late October, much of the country has chilled noticeably and is experiencing the first signs of winter. Things are a little different in Central Florida, where temperatures tend to hover in the 70s and low-80s.

Despite the warm weather, Winter Springs Hometown Harvest Fest is about as traditional as fall celebrations get. 

Held at Central Winds Park, this family event has live entertainment, pumpkin carving, painting contests, and hayrides too.

Naturally this is all a great time for kids, and there’s even more on the schedule for wee ones, with bounce houses, and ‘trunk or treat’.

13. Winter Wonderland

Winter Wonderland, Winter SpringsSource: City of Winter Springs / Facebook
Winter Wonderland, Winter Springs

Taking place in early December, Winter Springs’ Winter Wonderland Celebration has been wowing holiday lovers for nearly 40 years.

This is the longest-running of all of the city-organized festivals, and is sure to bring some extra joy to the holiday season.  

At the heart of the celebration is a Christmas tree lighting ceremony and parade. There’s also live music, food trucks, and all sorts of activities for children.

The event takes place at Winter Springs Town Center, and ushers in the Winter Wonderland of Lights. This is an adorable drive-thru light display at Central Winds Park. 

There you’ll get to see the curious spectacle of palm trees illuminated by twinkling lights. The display is usually in place for the weekend of the festival and the weekend after. 

The date will change year to year, so I’d keep an eye on the city’s website for exact details.

14. Central Winds Music Festival

Yet another date to mark in your calendar, the Central Winds Music Festival takes place in November. This event had just been launched when I was in town, and is all about live music, culture and diversity.

From morning to night there are constant performances from a big and wide-ranging lineup of musical acts.

Nationally renowned acts will headline, while earlier in the day you can see who’s making waves on Central Florida’s scene. There will also be a slew of food vendors, along with games and activities for all ages.

14 Best Things to Do in Winter Springs (FL):

  • Central Winds Park
  • Cross Seminole Trail
  • Spring Hammock Preserve
  • Black Hammock Airboat Rides
  • Bear Creek Nature Trail
  • Hidden Palms Ranch
  • Museum of Seminole County History
  • Trotwood Park
  • Scottish Highland Games
  • Oviedo Mall
  • Winter Springs Festival of the Arts
  • Winter Springs Hometown Harvest
  • Winter Wonderland
  • Central Winds Music Festival