Winter Park: Orlando's Hidden Gem

Winter Park is a must-visit destination for those who love history, high fashion and upscale dining.

Cobblestone streets, pristine lakes, world-class art and a lively downtown make Winter Park a must-visit destination for visitors and a beloved neighborhood for locals. 

Park Avenue

A long, bustling and walkable shopping and dining thoroughfare teeming with sidewalk boutiques, upscale retail and galleries with artsy jewelry and home décor, Park Avenue is where the action is. Park Avenue is lined with tall, leafy trees on the east side of the avenue and the charming Central Park on the west with rose gardens and shady benches, making this area one of the alluring shopping districts in the state. Cozy cafés and upscale restaurants speckled in between shops urge diners to sit outside and take in the elegant atmosphere buzzing around them. The north end is home to the Charles Hosmer Morse Museum of American Art, one of the region’s most prestigious museums with one of the world’s-largest collections of Louis Comfort Tiffany glass, sculpture and an entire chapel with stained-glass windows. The museum is a trove for late-19th and 20th-century American painting and decorative art.

College Charm

The historic charm of Winter Park is thanks in large part to Rollins College, the state’s oldest college, which was named for one of Winter Park’s founders, Alonzo W. Rollins. The jewellike campus, with its main gates within walking distance from the downtown core, sits on the shore of Lake Virginia. Huge cypress trees line the shore where wanderers can step onto a boardwalk leading to a gazebo overlooking the lake. Nearby, watch students piloting sailboats checked out from the campus boathouse, allowing Rollins students to take to the water at will. Besides enjoying the views and gardens, visitors can see the school’s Cornell Fine Arts Museum. The small but mighty galleries of this free and open-to-the-public museum showcase a private collection with pieces ranging from paintings by Georgia O’Keefe to photos by Chuck Close, as well as traveling shows by artists of national and international acclaim.

Fashion-Forward

Boutiques catering to the aesthetics of the hip college crowd and upwardly mobile fashionistas along with Winter Park’s more traditional shopping patrons make shopping Park Avenue and Hannibal Square a classy and stylish affair. The vibe is a mash-up of traditional Florida flair with more youthful chic of-the-moment. Locally owned shops take pride in presenting collections from top labels and designers. Hannibal Square Two blocks west of Park Avenue on New England Avenue is historic Hannibal Square. This area is ripe with day spas and salons if pampering is what you seek. Dining rooms both upscale and casual frequented by locals make this a popular destination for date nights and celebrations, along with casual brunches alfresco. If little ones are in tow, take them over to Shady Park where a cool splash pad draws them in to frolic among the gushing fountains. 

A Traveler’s Dream

Back in the heart of town, grab an iced coffee or an ice cream cone off Park Avenue and head across the street to Central Park. Pick one of the many inviting benches dappled in shade from the huge oaks and watch families and couples meander around the park’s graceful fountains and walking paths marked by rose gardens and enormous flowerpots. From here you can venture almost anywhere in Central Florida thanks to Sun Rail, Orlando’s new commuter train. On the west end of the park is the train depot where, on weekdays, you can climb aboard and head south to downtown Orlando or go as far north as Deltona. Just east of Park Avenue is Winter Park’s newest jewel, the Alfond Inn. This enchanting boutique hotel was recently recognized by Conde Nast and opened as a unique fund-raiser partner to nearby Rollins College. The lobby, suites and public spaces are adorned with fine contemporary art from notable artists, and Hamilton’s Kitchen is a popular spot for lunch and dinner among visitors and locals.

Farmers Market

Every Saturday, Winter Park becomes a destination for local produce and handcrafted foods. People from all over Central Florida flock to this large, boisterous farmers market in the heart of downtown to eat, drink and load their bags full of fresh veggies for dinner. Vendors’ wares include breads, muffins and bagels, live flowers and plants, herbs, local honey and big vats of kettle corn made on the spot.

Beyond the Avenue

Farther west visitors will encounter the busy shopping and dining destination of Winter Park Village. Just down the road from the new Trader Joe’s and Paddle Board Orlando on beautiful Lake Killarney lives this enclave of high-casual restaurants, entertainment and retail that packs everything for a great night out in one convenient and walkable location.

By Boat

One of the best ways to take in the beauty of Winter Park is by water. Visitors can get a view of the city’s postcard-perfect shores while onboard a relaxing and informative boat tour along the beautiful Winter Park chain of lakes and canals. Observe eagles soaring above and marvel at towering cypress trees, tropical birds and alligators sunning on the beach in front of a 19th-century mansion.

Cultural Treasures

Everyone who comes to Winter Park can’t help but have an opportunity to see great art. Catherine Hinman, the director of public affairs at the Charles Hosmer Morse Museum of American Arts says, “Although we have visitors from all over the world, our museum is still relatively undiscovered by many thousands of visitors who come to Orlando to enjoy the theme parks. Anyone with an interest in art—or American history for that matter—and who has a chance to travel to this city should not miss the Morse.”

“It is considered the most comprehensive and important collection of his works anywhere,” she says.  “Many people are familiar with Tiffany lamps and windows, but when they come to the museum, they are often astonished to see the range of his work. A highlight of a visit is always the Byzantine-Romanesque chapel interior Tiffany designed for exhibition at the 1893 World’s Fair in Chicago, which literally brought fair-goers to their knees and continues to mesmerize our visitors today.”

The museum permanently exhibits surviving objects and architectural elements from Tiffany’s grand, 84-room Long Island estate, Laurelton Hall.  

Another famous Winter Park cultural landmark is on Lake Osceola, the Albin Polasek Museum and Sculpture Gardens. Out on the museum’s grounds are a number of sculptures by the Czech artist plus a quiet garden with lake views. The small gallery inside the house-turned-museum features art from local painters as well as traveling exhibitions.

Visitors Welcome

“Winter Park has been attracting visitors for more than 125 years, when Northerners brought the train to town to escape from winter weather,” says Patrick Chapin, president and CEO of the Winter Park Chamber of Commerce. “Today, our community welcomes visitors from around the globe to experience our charming downtown filled with world-class museums, unique shops and sidewalk cafés.”

With a focus on the future and a spirit rooted in the past, Winter Park is a Florida treasure. For more information, visit the welcome center at 151 West Lyman Ave., or call 407.644.8281.

Shelley Preston
About the author

I was born and raised on Colorado’s Front Range, so Florida felt pretty foreign when I first moved here almost a do...