Road Trips

Winter Park Offers Small-Town Charm and History with Grown-Up Amenities

Winter Park's got Old Florida attractions, excellent restaurants and great shopping.

By Megan McDonald March 1, 2018 Published in the March 2018 issue of Sarasota Magazine

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Park Avenue offers a quaint collection of shops and restaurants.

I never thought much about growing up in Winter Park, just north of Orlando, when I was a kid. It was a pretty town—home to posh Park Avenue, the world-famous Morse Museum with its collection of Tiffany glass, and Rollins College’s beautiful, sprawling lakefront campus. But lots of it was still undeveloped. My brother and I used to feed the wild peacocks in the orange groves where a development of salmon-colored Med-Rev homes now stands.

As a child, Winter Park seemed kind of, well…boring.

Thankfully, perspective changes with age, and I’m now well-aware of the charms of my hometown (which was even named one of the best small-town escapes by Garden & Gun magazine back in 2015). Now, when I visit, I always try to take advantage of one of the town’s charming Old Florida attractions, or eat at one of its excellent restaurants. 

Winter Park is a two-hour drive from Sarasota; if you’re spending the night, make a reservation at the luxe Alfond Inn, which is owned by Rollins College and which took the place of the much-beloved old Langford Resort Hotel—where my parents held their wedding reception 38 years ago—after it was torn down. The Alfond is just steps away from Park Avenue, which should be your next stop; throw your bags on your bed and head out the door to explore. 

Park Avenue is Winter Park’s Main Street, home to a big, green park and packed with interesting shops and restaurants. In the spring, the annual Sidewalk Art Festival—now in its 58th year—takes over the park and welcomes tourists and artists from all over the world; over the holidays, there’s a huge tree-lighting ceremony and the entire avenue glitters with sparkly lights. Stop in for a bite and a beverage at Prato Restaurant, which serves seasonal, modern Italian food in a gorgeous space (you’ll want to Instagram the restaurant’s living wall). 

After you eat, grab a coffee for the road at Barney’s Coffee & Tea, then keep walking toward the Morse Museum, home to a globally recognized collection of pieces by Louis Comfort Tiffany, including glass lamps, windows, paintings, jewelry and more; admission is just $6. Beyond that, at the end of Park Avenue, is Casa Feliz, a historic home built by noted architect James Gamble Rogers II. It was saved from destruction in 2005 by a dedicated group of Winter Parkers who raised funds to pick up and move the house to its current location next to the Winter Park Golf Course. In addition to being a popular wedding venue (my husband and I got married there in 2016), it’s open for tours and presents weekly music programs.

Another museum option, also within walking distance of the Alfond Inn, is the Albin Polasek Museum & Sculpture Gardens, dedicated to the legacy of Czech-American sculptor Albin Polasek; it’s home to both a permanent collection and rotating visiting exhibitions. 

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Rifle Paper Co.'s sunny storefront.

A few blocks north, just across the train tracks, is the Hannibal Square area, where you’ll find more shops and restaurants, including the internationally renowned Rifle Paper Co., where owner and creative director Anna Bond sells her whimsical floral stationery and accessories out of a charming brick storefront (they’re also available online at Stock up on stationery, then head to dinner and drinks at The Ravenous Pig, a modern gastropub known for its house-made charcuterie and creative craft cocktails. 

Other must-dos: the one-of-a-kind Winter Park Scenic Boat Tour, during which visitors can pile into 18-passenger pontoon boats and take a historic tour of the Winter Park Chain of Lakes; a visit to the lakefront Kraft Azalea Gardens, where you can chill out with a book and a blanket and ogle the beautiful homes that flank the park; and, if you’re there on a Saturday, the bustling Winter Park Farmer’s Market, which is packed with local vendors. And don’t miss the opportunity for a (free!) round of golf at the eight-hole Winter Park Golf Course, or the chance to walk around Rollins College, which in addition to its beautiful Spanish architecture and lakefront location is home to several galleries and a historic chapel.

Insider Info

From Morse Museum director Dr. Larry Ruggiero 

“Winter Park is a pleasant, picturesque town. The people here want to keep it looking good, and it’s relatively quiet. But at the same time, it’s in a fair-sized metro area with national and international links, like the airport, colleges and attractions.”

“My wife and I enjoy Park Avenue. We love Miller’s Hardware.”

“There’s always something interesting going on at Rollins College—lectures, the Bach choir, etc.”

“Neither the City of Winter Park nor the Morse Museum do a tremendous amount of marketing, so Winter Park is a hidden jewel. For example, Hamish Bowles from Vogue happened to stop in Winter Park and wrote about it and the museum in the magazine. He loved it. That’s the kind of experience we want people to have.”

“Don’t miss the Laurelton Hall experience at the Morse Museum, which really enhances the collection, or The Domes of Yosemite by Albert Bierstadt, which is currently on loan from the St. Johnsbury Athenaeum in Vermont.”

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