14 Best Things to Do in Winter Springs (FL)

Written by Bart Meeuwesen
Updated on
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Located in north-central Florida’s Seminole County, Winter Springs is part of the Orlando, Kissimmee, Sanford metropolitan area and had a population of nearly 34,000 residents at the time of the last census.

Its central location makes travel to some of the state’s most popular tourist destinations easy and doable in a day, and the town is particularly well-known for the fairs, festivals, and holiday celebrations it hosts throughout the year.

Day trips to Daytona Beach and Cape Canaveral are popular options, and regardless of interests, finding ways to occupy your time won’t be an issue.

Below are 14 things to do in and around Winter Springs, Florida.

1. 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

During most of the fall and winter months, the Florida weather is downright perfect. For art-loving travelers who’ll be in Winter Springs in mid-October, there’s no better way to get your fill of mild sun and lovely art than spending some time at the Winter Springs Festival of the Arts.

It’s held at the Winter Springs Town Center and has been going strong for more than a decade.

Local, regional, and national artists will be on-hand displaying their creations, and the festival has gained quite a reputation for its tasty food options too.

Check out Winter Springs’ website for more information.

2. Winter Springs Hometown Harvest

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

In November when much of the country has chilled noticeably and experienced the first signs of winter, Floridians are usually basking in the sun and temperatures that tend to hover in the 70s and low-80s.

For many Northeasterners and Midwesterners, it may not sound like traditional fall weather, but Winter Springs Hometown Harvest Fest is about as traditional as fall celebrations get, and includes live entertainment, pumpkin carving, painting contests, and hay rides too.

Like the arts festival mentioned above, it’s held at the town center and is known for its tasty food options provided by local restaurants and amateur chefs.

3. Winter Wonderland

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

Be warned; Christmas scenery in Florida may include swaying palm trees, temps in the 80s, and bathing suit-clad revelers wearing red Santa hats.

Taking place on December 7th, Winter Springs’ Winter Wonderland Celebration has been wowing holiday lovers for nearly 40 years.

Of all the festivals the city hosts, it’s one of the longest-running perennial favorites and includes more activities than it’s possible to list.

Suffice it to say that boredom won’t be a problem, and with a Christmas tree lighting ceremony, parade and even dance classes, there’s a little something for everyone regardless of age and interests.

4. Scottish Highland Games

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

Taking place over two days in mid-January 2020, Winter Springs’ Scottish Highland Games is another of the city’s long-running events that’s a trans-Atlantic celebration of all things Scottish, and primarily focuses on the roles Scottish immigrants have played in the settling and development of the area.

The games are held at the ever-popular Central Winds Park, and after more than four decades, have attracted quite a following.

Many guests have been attending for years, and with such a variety of highland games, dancing, and culinary creations, it’s no wonder.

It’s a unique opportunity at cultural immersion, whether you’re from Scotland, Iceland, Vietnam, or anywhere else for that matter.

5. Central Winds Park

Central Winds ParkSource: kellyv / Flickr
Central Winds Park

Featuring baseball fields, basketball courts, fishing piers, and nature trails, it’s easy to see why Central Winds Park is such a popular attraction for sports and nature lovers who want to get outside and burn some calories without wasting valuable time behind a dirty windshield.

Central Winds Park is located on the southwest corner of Lake Jesup, and in addition to the previously mentioned amenities, includes covered pavilions, picnic areas, a dog park, and playgrounds for the little ones.

It’s a great place to catch a little league game or just take an afternoon stroll along the paved paths as the sun dips below the horizon.

6. Winter Park’s Park Avenue Shopping District

Winter Park’s Park Avenue Shopping DistrictSource: Park Avenue, Winter Park / Facebook
Winter Park’s Park Avenue Shopping District

For more than a decade, the area that’s now the Park Avenue Shopping District has been a popular city attraction and winter retreat for wealthy northeast and Midwesterners intent on escaping winter’s unpleasant grasp in their home cities.

Now, it’s one of the area’s most trendy retail centers, and home to a thriving collection of restaurants, bars, shops, boutiques, galleries, and museums. For those who’d rather get the essence of the area in one location, there’s no better place to do it.

Featuring live entertainment, a great farmer’s market, and a relaxed and cultured environment, it’s no wonder it’s often referred to as Florida’s ‘Little Europe.’

7. Charles Hosmer Morse Museum of American Art

Charles Hosmer Morse Museum of American ArtSource: 407apartments.com / Flickr
Charles Hosmer Morse Museum Of American Art

Louis Comfort Tiffany was a world-renowned artist and craftsman who lived from the 1840s until the 1930s and was most well-known for his glass and cast bronze lamps.

Sporting the world’s most complete collection of works by Tiffany, the Charles Hosmer Morse Museum of American Art is another of Winter Park’s cultural and artistic icons that’s easily accessible for those staying in nearby Winter Springs.

The items on display include pottery, paintings, jewelry, and leaded glass. Much of it was originally housed in the artist’s home and studio in Long Island, New York. The museum is open year-round but closed on Mondays.

8. Park Avenue Food Tour

Park Avenue Food TourSource: Orlando Food Tours / Facebook
Park Avenue Food Tour

With dozens of restaurants featuring everything from traditional American fare and amazing seafood to dishes with international influences from South America, Europe, and Southeast Asia, finding delectable things to fill your grumbling stomach won’t be a problem when visiting Winter Park’s Park Avenue.

Be warned that it’s not known as a place to pick up good-eats on the cheap, but with a little effort, you’ll probably be able to find someplace reasonably affordable.

Featuring wine bars and local microbreweries, coffee shops, bakeries, and full-service restaurants of nearly every description, it’s the kind of place epicurean travelers tend to congregate in large numbers.

9. Winter Park Farmer’s Market

Winter Park Farmer’s MarketSource: PauloAlmeidaPhotography / shutterstock
Winter Park Farmer’s Market

Winter Park and Winter Springs are just 10 minutes from one another by car, and between the two of them, there’s nearly always something going on to entice energetic travelers.

The Winter Park Farmer’s Market takes place at the town’s historic train depot and is held on Saturdays from 7 AM until 1 PM.

The market is known for its fresh baked goods, amazing, locally-grown fruits and vegetables, health and body products, and its prepared food items like salsa, honey, and pasta sauce.

Farmer’s markets are great places to meet locals and pick-up a few recommendations for things to see and do that you might’ve missed otherwise.

10. Cornell Fine Arts Museum

Cornell Fine Arts MuseumSource: Ebyabe / Wikimedia
Cornell Fine Arts Museum

Located on the scenic campus of Rollins College overlooking nearby Lake Virginia, the Cornell Fine Arts Museum’s collection includes thousands of pieces of art and is widely recognized as one of the state’s most complete repositories.

Unlike many small college museums that are sadly underfunded and unimpressive, Cornell is known as a sophisticated innovator and includes pieces dating from medieval and renaissance Europe all the way up to the present.

Many international and cultural influences are represented, and most visitors find the scope and contrast of the works to be impressive.

The museum is open year-round from Tuesday to Sunday.

11. Magic Kingdom Park

Magic Kingdom ParkSource: danmattgreen / shutterstock
Magic Kingdom Park

Located on the grounds of world famous Disney World in Orlando, Magic Kingdom Park is one of those Florida theme park icons that really doesn’t need an overly wordy introduction.

Known for its Cinderella Castle and abundant movie and cartoon characters like Donald Duck and Mickey and Minnie Mouse, it’s a virtual wonderland for traveling families, and one of those attractions that really shouldn’t be passed up.

The Kingdom is divided into distinct areas that include Main Street USA, Tomorrowland, and Liberty Square.

There are just too many dining, retail, and activity options to list, so spend a little time checking out their website before making the trip.

12. LEGOLAND Florida

LEGOLAND FloridaSource: Rob Hainer / shutterstock

Sprawling over more than 100 acres on the shores of Lake Eloise in nearby Winter Haven, LEGOLAND Florida is one of the world’s most extensive facilities dedicated to inspiring creativity in young minds.

Designed primarily with preteen children in mind, it’s full of a fantastic array of interactive exhibits, live performances, and guided activities that are engaging, educational, and downright fun.

The park is laid out in distinct zones and is relatively easy to navigate, even when it’s filled to capacity.

There are a variety of shops and restaurants on site and a popular waterpark that’s a big hit during the dog days of summer.

13. Lake Buena Vista Factory Stores

Lake Buena Vista Factory StoresSource: VIAVAL / shutterstock
Lake Buena Vista Factory Stores

Sometimes even the most diehard nature lovers and beachgoers tire of the toasty Florida sun and miles of coastline; for those looking for a pleasant change of pace and a little air-conditioning, there’s no better place to spend a few hours than the Lake Buena Vista Factory Stores.

Featuring 50 outlets, including internationally famous brands like Calvin Klein, Nike, and Tommy Hilfiger, it’s a retail therapy hotspot. Since there are plenty of dining and kid-friendly activity options nearby, it’s the kind of place that visitors often end up staying at for longer than expected.

The stores are located on State Road 535 in Orlando, and for savvy shoppers looking to save a few bucks, it’s often possible to find coupons online and in travel magazines.

14. La Cava del Tequila

La Cava del TequilaSource: Theme Park Tourist / Flickr
La Cava Del Tequila

Featuring more than 100 varieties of Tequila from south of the border, La Cava del Tequila in Disney’s Epcot World Showcase is a destination best enjoyed by childless travelers, or at least those who’ve pawned their little ones off on unsuspecting in-laws for a few hours.

For those with little or no tequila experience, it’s best to try a sampler, as it’ll give you small amounts of a variety of tequilas. If mixed drinks are more your thing, there’s an unbelievable selection of those as well.

La Cava del Tequila is also known for its tasty and traditional Mexican dishes; many are prepared with local ingredients and contemporary twists.

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

  • Winter Springs Festival of the Arts
  • Winter Springs Hometown Harvest
  • Winter Wonderland
  • Scottish Highland Games
  • Central Winds Park
  • Winter Park’s Park Avenue Shopping District
  • Charles Hosmer Morse Museum of American Art
  • Park Avenue Food Tour
  • Winter Park Farmer’s Market
  • Cornell Fine Arts Museum
  • Magic Kingdom Park
  • LEGOLAND Florida
  • Lake Buena Vista Factory Stores
  • La Cava del Tequila