Read Time: 12 mins.
Table of Contents
Introduction
After a few days of thrilling rides and non-stop excitement in Orlando, why not take a breather and explore a side of Orlando that’s just as enchanting but a bit off the beaten path?
Luckily, just a short drive from downtown and Disney, you’ll find Winter Park, a beautiful little town perfect for a relaxing day out. With a breath of fresh air, charming streets, friendly faces, and beautiful scenery, it’s a place where you can witness and soak in some of Orlando’s more laid-back beauty.
So, if you’ve got a few extra days to spare, here’s a guide to the top things to do in this lovely town.
15 Must Things To Do at Winter Park Orlando
Winter Park, Orlando, is like a little slice of ancient Florida blended with modern entertainment. As someone who has been Uncovering Orlando for over 25 years, I’ve visited the municipality dozens of times and have never left unhappy. Here’s a list of 15 activities you must do in Winter Park. Trust me, you’ll want more.
1. Visit the Charles Hosmer Morse Museum of American Art
Thinking “museum,” is not my type? No, my dear. Count on me; you have to visit this museum at least once. Even if you’re not typically into museums, the Morse is different. Walking through the galleries is a feast for the eyes.
Housing over 1,000 works by Louis Comfort Tiffany, including 250 stained glass windows (not just for churches, of course), this museum is a perfect example of stunning art. Plus, the atmosphere is so serene that you can lose yourself for hours. The $6 entry fee for adults is a steal for the experience you get, and children under 12 can enter for free.
Suggested Reading → Best Museums in Orlando.
2. Explore Park Avenue in Winter Park
If you’re looking for lively things to do at Winter Park, Park Avenue is the beating heart of the town.
With 140+ boutiques and 25+ restaurants lining the streets, there’s no shortage of ways to spend your day. Whether you’re sipping on a cappuccino at one of the 30+ outdoor cafes or splurging on unique finds at local shops, this stretch of Winter Park feels like a slice of Europe.
And the food?
Oh my gosh, the restaurants will have your mouth watering just walking by. It’s a place where you can stroll, shop, and dine- all in one go.
3. Shop and Eat at the Farmers Market on Saturdays
Now, you can’t miss the Farmers Market if you’re in town on a Saturday. It’s hands down one of the best things to do at Winter Park, especially if you love fresh, local finds.
With 40 local vendors offering fresh produce, homemade goods, and everything in between, it has become a community staple, with thousands of visitors stopping by each week.
The rows of colorful produce and the smell of freshly baked bread in the air are the true vibes of the place.
We never miss it. My kids and I always snag kettle corn and lemonade while browsing the seasonal picks. It’s held at a historic train depot and runs from 7 a.m. to 1 p.m., so get there early to snag the best finds.
4. Check Out Plant Street Market
Just a 20-minute drive from Winter Park, Plant Street Market is more than just a food hall. It’s a local favorite, a place you can just be. With over 20 traders under one roof, it’s your go-to spot for everything from craft beer to gourmet pizza. The hardest part is choosing what to eat because it’s all so good.
For me, the famous Crooked Can Brewery is a standout, offering 15 rotating taps of locally brewed beer. Yet their macaroons are worth trying, too. I’ve been going here for years, and it never disappoints.
5. Enjoy a Scenic Boat Tour
One of my all-time favorite things to do at Winter Park is the Scenic Boat Tour. This is the time if you’ve never experienced Winter Park from the water. This peaceful, hour-long airboat ride takes you through three of Winter Park’s beautiful lakes, connected by narrow canals and lush greenery. You’ll pass by some multi-million-dollar homes beautifully preserved and learn about the town’s history from expert guides.
It’s affordable, too, at $16 for adults and $8 for kids. This tour is a relaxing and scenic way to see a side of Winter Park you’d never get from the streets alone.
6. Tour Rollins College for History and Beauty
Rollins College is more than just a prestigious institution; it’s one of the most beautiful campuses you’ll ever walk through. With over 70 acres of Spanish-style buildings and blooming gardens, you’ll find yourself completely enchanted by the surroundings. Plus, it’s home to the Rollins Museum of Art, which houses 5,000+ works of art, all for free.
The college is over 130 years old, steeped in history, and offers idyllic views of Lake Virginia that’ll make you want to return to college yourself (well, maybe not). Verily, just walking around Rollins makes you feel a little fancy. Make sure to capture pictures of your Instagram feed. I will thank you later.
7. Go Shopping
If shopping is your thing, Winter Park has you covered. Begin on Park Avenue, where upscale boutiques tempt you with high-end fashion, quirky gifts, and everything in between. If you’re in the mood for mainstream brands, head to Winter Park Village for some serious retail therapy.
Feeling fancy?
Swing by The Mall at Millenia for a luxe shopping experience – Louis Vuitton, anyone?
For foodies, visit The Ancient Olive, where you can sample over 20 varieties of gourmet olive oils. My kids know it’s a guaranteed stop whenever we’re nearby because I can’t resist.
More of a shopping freak? Visit my guide to learn more about Best Shopping Malls in Orlando.
8. Stroll Through Mead Botanical Garden
Are you in the mood to escape into nature? Mead Botanical Garden is one of the best things to do at Winter Park. Spread over 48 acres, it’s a peaceful haven for nature lovers. You’ll find walking trails, butterfly gardens, and an amphitheater for outdoor concerts.
It’s also a hotspot for birdwatchers, with more than 100 bird species calling it home. Best of all, it’s completely free. Pack a picnic, grab a good book, and enjoy the tranquility of this natural oasis. After a few hours here, you’ll feel like you’ve left the city behind.
9. Relax in Central Park
Central Park is the soul of Winter Park. With 11 acres of open green space, It’s perfect for a picnic or just letting the kids run wild. We’ve spent countless afternoons here, just soaking in the fresh air. Don’t miss the rose garden – it’s beautiful.
It also hosts the famous Winter Park Sidewalk Art Festival, which draws over 350,000 visitors each year. Bring a blanket, grab a book, and enjoy the serenity if you want a low-key day. Both locals and tourists gather to take in the simple pleasures, perfect for a family day out.
10. See a Show at The Winter Park Playhouse
Looking for a unique evening out?
The Winter Park Playhouse is a 123-seat theater that hosts Broadway-quality musical performances in an intimate setting. This local gem puts on about 8 productions a year, with tickets ranging from $20 to $45 – a steal for the quality. The shows are always packed with energy and heart, making it an unforgettable experience. I remember catching a one-man show here, and it was unforgettable.
11. Grab a Burger at BurgerFi
Hungry?
BurgerFi is the place to hit when you want a no-fuss, delicious burger. Their Angus beef patties are seriously the best, and the fries are crispy perfection. Plus, on Mondays, kids eat free with a purchased adult meal.
Win-win!
It’s fast, casual, and family-friendly; the shakes are to die for. Don’t miss this spot if you love a good burger (and who doesn’t?). It’s always worth the visit, and trust me, you’ll leave full and happy.
12. Step Back in Time at Winter Park Train Station
Trains, trains, and more trains! If your kiddos are train lovers like mine, they’ll be thrilled to stop by the Winter Park Train Station. Watch the Amtrak and SunRail trains roll in and out of this charming, historic station. It’s fun, affordable, and a great way to explore Central Florida if you don’t like driving. There’s plenty of free parking and tons of shops and eateries nearby. Plus, the air-conditioned train ride is a godsend during hot days. It’s like a mini adventure for the whole family.
13. Stay at Winter Park’s Beautiful Resorts
Planning to stay at Winter Park? Great! The town has some truly beautiful places to stay. The Alfond Inn, with its 112 rooms and stunning architecture, is a great choice if you want a little luxury.
On the more intimate side, Casa Feliz is a charming Spanish-style farmhouse that feels like a romantic getaway. Winter Park also offers a range of Airbnb options for families, from quaint cottages to modern homes. No matter your budget or style, Winter Park has a stay that will make you (and your guests) fall in love with the area.
14. Take Kids to Shady Playground
If you’re traveling with kids, you’ll want to know where the best playgrounds are, and Winter Park has some great options. The Community Playground affectionately called the “castle park,” is always a hit with its wooden forts, slides, and swings.
It’s spacious and perfect for letting the little ones burn off energy. I’ve spent countless afternoons here with my little ones, watching them climb, run, and play while I enjoy a bit of downtime. It’s where kids can be kids, and you can relax, knowing they’re in a safe, fun environment.
15. Paddle Up on Lake Virginia
Paddleboarding on Lake Virginia is the way to go for those craving adventure. You’ll glide across the shimmering waters, surrounded by the beauty of Rollins College and lush greenery. It’s peaceful yet exhilarating, and the kids will love the chance to try something new. Don’t worry if you’re a beginner; the calm waters make it an ideal learning spot.
More Things To Do at Winter Park
While I have only mentioned a handful, there are many other sites to discover. Here are a few more to ensure you don’t miss out on the best parts of Winter Park.
- Enzian Theater: for independent films and dining
- Cornell Fine Arts Museum: for an array of artworks.
- Lake Lily Park: for a family picnic.
- The Grove: a great place for brunch or coffee.
- The Winter Park Historical Society: For more information on local heritage,
- Winter Park Golf Course: for a round of golf
- Albin Polasek Museum & Sculpture Gardens: to watch sculptures.
- The Winter Park Public Library: to browse books or attend community events.
- The Little Blue Box Bakery: for delicious cupcakes and treats.
Ready To Explore?
Winter Park is more than simply a location on a map; it’s a destination full of charisma, history, and amusement for all travelers. Whether you’re sipping coffee by the lakes, strolling down Park Avenue, or watching the sunset at Mead Botanical Garden, there’s plenty for all beings. So mark the spot for your upcoming Orlando trip and let Orlando one of those beauty chapters unfold.
FAQs
How can I enjoy Winter Park’s outdoor activities?
You can enjoy outdoor activities by exploring the picturesque Lake Virginia on a boat tour, strolling through the lush Kraft Azalea Garden, or biking along the scenic Cady Way Trail.
What is the best time to visit Winter Park?
The best time to visit Winter Park is during the fall and spring when the weather is pleasant and outdoor activities are possible without the sweltering heat.
Are there any cultural events or festivals in Winter Park?
Winter Park hosts several cultural events and festivals throughout the year, including the Winter Park Sidewalk Art Festival and the Bach Festival.
Can I visit Winter Park on a budget?
Absolutely! Many attractions in Winter Park, like scenic parks, gardens, and public events, are free or low-cost, making it easy to explore on a budget.
What transportation options are available in Winter Park?
Winter Park offers various transportation options, including a free trolley service, bike rentals, and ample parking for those who prefer to drive.
