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Taking an Interesting Day Trip to Winter Park, Florida

Taking an Interesting Day Trip to Winter Park, Florida

Winter Park, a tree-lined cobblestone street neighborhood, is on the outskirts of Orlando in the northern corner. Home to Rollins College, a prestigious college, and 11 acres of gorgeous park landscape, Winter Park was a popular winter resort attracting the rich and famous Northerners in days gone by. It is also an excellent place to take a road trip and enjoy a few hours exploring the beautiful Florida town. Here are my suggestions for taking a day trip to Winter Park.

cafes and shops lining the street in winter park fl

Arriving for Your Day Trip

Depending on the day of the week you choose to visit Winter Park, there may be special events taking place. Regardless, parking is free for three hours on the streets. Park Avenue is the main thoroughfare running through Winter Park, so park close to the action.

If you are there in time for breakfast, grab a fantastic Colombian coffee and mixed berries with Nutella toast from CFS Coffee. For a more filling meal, KeKe’s Breakfast Cafe features delicious omelets, pancakes, waffles, and stuffed French toast. The Banana Split Waffle is to die for!

Saturdays bring the Winter Park Farmers’ Market at Central Park West Meadow near the old train depot (corner of New York Avenue and Morse Blvd.). A selection of gourmet foods, plants, herbs, gifts, and more await those who attend this weekly event. Hours for the market are 8 AM to 1 PM.



Winter Park’s shopping scene is pretty incredible. There are street after street of boutique shops and galleries (since 1887), sandwiched in between sublime restaurants and wine bars. For ladies apparel, you’ll love Lilly Pulitzer, Siegel’s, and Versona. Patridge Tree Gift Shop is a great store to shop for home accessories and things you didn’t know you needed, but can’t live without now that you’ve seen them. For kid’s, Maison Drake is excellent for baby needs and clothing.

beautiful street with hanging baskets

I can’t imagine a Winter Park visit without choosing a couple of decadent Peterbrooke Chocolatier’s European chocolates to enjoy along the way, and browsing the incredible selection of books and gift items at Writer’s Block Bookstore.

shopping in winter park florida

Be sure to step inside the Spice and Tea Exchange, serving a wide array of hot and cold tea selections. They also have loose spices and teas, available in any quantity, along with recipes for how to use them. I found the staff there very friendly and helpful.

spice and tea exchange

Parks, Museums, and Art

Stunning parks dot the landscape in Winter Park, with three gorgeous fountains, flower beds, and loads of oak trees. You’ll be impressed with the pristine 11 acres of park literally in the midst of the historic town. It is normal to see people and families of all ages out enjoying the sprawling grounds, reading, relaxing, people-watching, or picnicking.

flowers and gazebo in winter park

Also in Winter Park is Rollins College, sitting on a beautiful campus with Spanish-Mediterranean architecture. It was the first four-year university in Florida and carries a respected reputation.

rollins college gates

Indulge in a fantastic art scene in Winter Park at the Charles Hosmer Morse Museum of American Art, home to the world’s largest collection of Louis Comfort Tiffany works. Items on display range from windows to lamps and are absolute masterpieces. You’ll find the museum on the Rollins’ college campus.   

winter park fountain and sculptures
sprawling winter park

An adorable museum to browse is the Winter Park History Museum, located in a former railroad freight depot. The museum, with children’s programming and speaker series, has changing exhibits, and always interesting and educational ones. It reopens to the public on June 17th.


Lunch or Dinner

Swine & Sons is a delicious place to have a tasty and hearty Southern-inspired lunch. In a shared venue with an upscale grocery, The Local Butcher and Market, Swine & Sons is a counter-order eatery where food is made fresh-to-order. The Hot Chicken and fries is every bit as good as the Nashville’s signature item, and the Pressed Italian sandwich is full of bold flavors. 

The Local Butcher and Market Winter Park

If BBQ isn’t your pick, you’ll find a little of everything in Winter Park: American, French, Thai, Italian, and Turkish. Tabla Indian and Bosphorus Turkish Cuisine are two of the top rated and visited restaurants in the area.


A little historical info about Winter Park is that it was for the elite to use as a winter getaway from the blustery Northern landscapes. The planned city first started with a park and Main Street (now Park Avenue), like most. Then came a railroad passenger depot, a way for the Northerners to arrive, a hotel, and grand shopping attraction. Winter Park was surrounded by orange groves and offered access to enticing lakes.

Attractions and local shops grew due to popularity of Winter Park, and soon a blacksmith, icehouse, and bakery were opened. Rollins College came about in 1885 and was the first higher learning institution in the state.

Still today, Amtrak and SunRail visit this historic and beautiful train depot.

winter park fountain with harp player

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