This October marks 132 years since Winter Park was incorporated as a town. According to the City of Winter Park, the initial purpose of the area was to provide refuge for northerners looking to escape cold winter temperatures. Now an esteemed year-round hotspot within Central Florida, the city remains, in a sense, a refuge for both residents and visitors. Full of parks, museums, brick roads and architecture, Winter Park has no shortage of artistic beauty. Park Avenue, the quaint main drag, is lined with numerous boutiques and critically-acclaimed restaurants that, undoubtedly, add flavor to Orlando’s expanding local food scene.
Here’s a snapshot of where to experience the best of Winter Park.
Park Avenue & the Surroundings
Downtown Park Avenue is undeniably the best-known strip of Winter Park. This prevalent street is lined with historic buildings, many of which now house shops and eateries while maintaining their original charm. For a lesson on the city’s history and an up-close look at the chain of lakes, the Winter Park Scenic Boat Tour is a must-do excursion. The outing lasts approximately one hour and departs daily on the hour, from 10 a.m.-4 p.m. Aboard a pontoon-style boat, you’ll coast by notable sights like the beautiful Kraft Azalea Gardens and the former home of the beloved Mr. Rogers, who graduated from Rollins College in 1951. For more lakeside leisure, you can launch a kayak from Dinky Dock Park, adjacent to the university.
Retreat to picturesque Central Park to take in gorgeous greenery right on the Avenue. Typically held on the second Thursday of the month at 8 p.m., this nature space transforms into an outdoor movie venue for Popcorn Flicks In The Park, courtesy of Enzian Theater. The family-friendly films are free; all you need is a cozy picnic blanket or chairs and snacks. Peterbrooke Chocolatier is close by, and their famous chocolate-covered popcorn or gelato will definitely meet your movie munching needs.
Brunching on the Avenue is a breeze thanks to restaurants galore. The Briarpatch hits the spot with tasty griddle favorites like blueberry-stuffed pancakes, and specialties like the pork belly waffle and smoked salmon benedict. With a farm-to-table focus, Boca has a number of appetizing flatbreads and salads. And, for a morning perk, Barnie’s Coffee Kitchen has delicious lattes and energy-packed oatmeal and toasts. All three of these restaurants offer alfresco seating so you can drink up the scenery with every bite. Just across the street from Boca, you’ll find the Morse Museum of American Art, showcasing paintings and pottery, in addition to the largest collection of Louis Comfort Tiffany. Visit in the months of November through April and take advantage of free admission on Fridays from 4-8 p.m.
Lunch options on the Avenue are easy to come by too. Bosphorous serves flavorful Turkish cuisine, while Prato’s specializes in Italian dishes like wood-fired pizza. Garp & Fuss is another epicurean gem, located in an elusive secret garden. Drinks and eats in their solarium are bound to be a relaxing break from the Avenue, which can get quite busy on weekends. The secret garden is also home to The Ancient Olive, a gourmet shop selling handmade pastas, a myriad of olive oils and vinaigrettes, as well as hosting hands-on workshops and food tastings.
Wander off Park Avenue to find even more local merchants of all kinds. New General, a coffee shop and general store, has local coffee, healthy eats and an array of products such as magazines, plants and home decor. Writer’s Block Bookstore not only carries independent books as well as bestsellers, but they also host frequent author events. Make your way to The Alfond Inn to marvel at the stunning art that graces the lobby, which courtesy of the Cornell Fine Arts Museum at Rollins College. The hotel’s restaurant, Hamilton’s Kitchen, is another popular brunch spot. And if you visit Winter Park via the SunRail, dine close to the train station at The Coop, a family-friendly eatery known for some of the most authentic southern food in the area.
The Winter Park Farmers Market is held every Saturday morning from 7 a.m.-1 p.m. in the old train depot. You’ll find a bevy of local purveyors selling organic juices, produce, plants, fresh flowers and more. Once you’ve worked up an appetite, nibble your way through the onsite food vendors. Another popular event that takes place here is the Winter Park Sidewalk Art Festival, always held on the third Saturday in March [note: this is the only Saturday that the farmer’s market is closed]. One of the nation’s largest outdoor art festivals, artists and art aficionados alike flock to Winter Park from all over the world to attend this yearly show.
Meander just a bit from the main drag to find Hannibal Square, featuring relaxed dining, romantic date night destinations, unique boutiques and a local wine bar, among other sites. A bit of a contrast to bustling Park Avenue, Hannibal Square boasts a more intimate atmosphere, while still exuding the charisma Winter Park is notorious for. Stationery brand Rifle Paper Co., loved for its hand-drawn florals and vibrant colors, has its flagship location here on Pennsylvania Avenue.
When hunger strikes, pop into Pepe’s Cantina for delicious Tex-Mex and a spirited outdoor bar with a generous happy hour (11 a.m.-7 p.m. daily). Dexter’s is legendary for its Sunday brunch and nightly live music. For a more casual meal, try Sausage Shack or an acai bowl at CFS Coffee. Vinia Wine Bar carries a vast selection of vinos from Europe in a contemporary setting and, thus, makes for an attractive date destination. For a romantic dinner, there are a number of other date night worthy options. Chez Vincent and Hannibal’s on the Square both specialize in French cuisine. Armando’s is the place for Italian fare and Mynt Fine Indian Cuisine is another favorite rounding out the diversity within Hannibal Square.
Orange Avenue & Fairbanks Avenue
South Park Avenue leads you to the prestigious Rollins College, a private liberal arts school recognized as Florida’s first college. The Cornell Fine Arts Museum is located on the Rollins College campus, but is open to the public with free admittance. There are a number of other cultural stops in this region, including the Albin Polasek Museum and Sculpture Gardens. This museum overlooks Lake Osceola and includes artist Albin Polasek’s home, sculpture garden, chapel and gallery. In addition, the Casa Feliz Historic Home Museum is open to the public every Sunday from 12-3 p.m., allowing visitors to wander through the home and enjoy live music thanks to the Music at the Casa series. Docent-led tours are also available during these times.
Dining options on this side of Winter Park range from plant-based to BBQ to Orlando’s yummiest tacos. Ethos Vegan Kitchen cooks up hearty meals comprised with mostly organic ingredients. If you’re in the mood for a crispy hot chicken sandwich or a sharable charcuterie plate, grab a table at Swine & Sons, located inside The Local Butcher & Market. Praised by locals and critics, The Ravenous Pig will wow you with stunning interior, beer brewed in house, craft cocktails and inventive fare featuring modern American cuisine. The Porch offers a playful dish called TV Dinner, complete with your choice of hot dogs or chicken tenders, mashed potatoes with gravy, macaroni & cheese, corn on the cob and a Little Debbie snack for dessert.
Krungthep Tea Time serves unique sandwiches and has a wide variety of teas and desserts, such as their impressive Strawberry Cheesecake High Hat. Enter through Buttermilk Bakery’s door and arrive at pastry heaven, with fresh baked croissants, cookies and savory selections too. All these food options will fuel you up for exceptional shopping and another must-experience place: The Heavy. This beautiful shop offers a perfectly curated selection of gifts and decor, great local coffee, a flower bar and a myriad of plants both large and small. If you love fashion and all things vintage, Avalon Exchange sells gently-used threads and accessories you won’t find at a typical thrift store.
Cross over 17-92 to find some of Orlando locals’ best bites. For example, BBQ lovers will dig 4 Rivers Smokehouse and its scrumptious brisket. Meanwhile, just a couple blocks down, Hunger Street Tacos offer a fresh, creative and authentic twist on tacos, quesadillas and desserts.
More on Orlando Avenue & the Surroundings
Orlando Avenue offers its own selection of memorable finds. Mead Botanical Gardens is one of the best places to explore the natural beauty of Winter Park. This free sanctuary provides visitors plenty of open space to stroll, plus a butterfly garden and hiking trail.
When you’re craving bottomless sangria and mimosas on the weekend, Bulla Gastrobar is the place to be. They also have a tapas happy hour that spans all week from 4-7 p.m. Once you’re finished your meal, sweeten your day at The Glass Knife. While they also offer breakfast and lunch, the cakes, donuts and pastries will have you sweetly hooked.
Located in Winter Park Village, find some of the tastiest slices at Pizzeria Valdiano. This local restaurant has won “Best Pizza” in Orlando for several years. You can get a whole pie or just grab a slice. Have a hankering for something more upscale? The Hangry Bison boasts a great mixture of hand-built burgers, fine bourbon and locally-brewed craft beer.
You see… Winter Park really is a year-round hotspot, no matter the season!