Like a Local: The City of Winter Park

Learn about the dining, culture, shopping and gorgeous nature that make Winter Park a favorite among Orlando’s locals.

Learn about the dining, culture, shopping and gorgeous nature that make Winter Park a favorite among Orlando's locals.

By Nate Shelton

Think you know Orlando? If you've only experienced our tourism districts, think again. Throughout the area, unique cities and neighborhoods offer outstanding restaurants, vibrant arts and culture, bespoke retailers and outdoor adventures, and the City of Winter Park is one of the best. If you haven't been there yet, you owe yourself a visit — here's why!

Getting to Know Winter Park

Approximately 20 minutes northeast of downtown Orlando, and not to be confused with Winter Garden to the south, Winter Park gained its name after the arrival of the South Florida Railroad in 1880. The highly rated Rollins College — Florida's first four-year university — opened shortly thereafter, heralding the city's refined future.

Today, Winter Park's epicenter is Park Avenue, a tree-lined, cobblestoned street bursting with acclaimed eateries, museums and some of the Orlando area's best shopping. The city also has much for outdoor enthusiasts, including a robust parks system and a gorgeous chain of lakes.

To really experience Winter Park, you'll want to stick around for a few days, and one of the best places to do it is The Alfond Inn. Owned and operated by Rollins College, it boasts 112 guest rooms, a full range of amenities (including a pool) and a riveting art collection. What's more, all of the hotel's profits endow a scholarship program at Rollins.

Learn more: Orlando Hotels & Resorts

Dining in Winter Park

Some of Orlando's top culinary artists ply their trade in Winter Park, including James Beard-nominated Chefs James and Julie Petrakis of The Ravenous Pig, a seasonal gastropub. (You can also try their fare at The Polite Pig at Walt Disney World Resort's Disney Springs.)

Learn more: Orlando Restaurants

Another key Winter Park chef is Brandon McGlamery, who has two restaurants on Park Avenue — Luma on Park and Prato — with a third in nearby Maitland at Luke's Kitchen and Bar. They specialize in progressive American, innovative Italian and classic American cuisine, respectively.

Other local favorites in the Park Avenue area include steaks and seafood at Blu on the Avenue, Umi Sushi, French cuisine at Chez Vincent and The Alfond Inn's fresh-focused Hamilton's Kitchen. Just a short drive from the city's core, enjoy Spanish cuisine at Bulla Gastrobar, seafood at Reel Fish Coastal Kitchen and world-class desserts at The Glass Knife, among other options.

Shopping in Winter Park

Shopaholics will love Winter Park's exquisite array of retailers, many of which are on and near Park Avenue. For instance, homegrown boutiques like Tuni and John Craig will have adults looking their best, while Tugboat & The Bird and Bebe's and Liz's will do the same for children.

Learn more: Orlando Shopping

You'll also find outposts from nationally recognized retailers Lilly Pulitzer and J. McLaughlin. Both are part of the lineup at Shops on Park, which offers 20,000 square feet of shopping and dining on Park Avenue.

And yes, you can buy more than clothes in Winter Park! Specialty merchants include Peterbrooke Chocolatier, Williams-Sonoma and Writer's Block Bookstore, to name a few. On Saturdays, the city offers even more unique shopping at the Winter Park Farmers' Market.

For still more retail opportunities, make the short drive from Park Avenue to Winter Park Village. The outdoor shopping center has a host of stores and restaurants, plus one of the area's best movie theaters.

Arts & Culture in Winter Park

Feed your inner artist at Winter Park's galleries and museums, including Rollins College's Cornell Fine Arts Museum, which offers free admission. This facility's collection — more than 5,500 pieces from the ancient to modern periods — is so expansive that a portion is displayed as the Alfond Collection of Contemporary Art at The Alfond Inn.

Learn more: Orlando Arts, Culture & History

Nearby, you can peruse the world's largest collection of Louis Comfort Tiffany's creations at The Charles Hosmer Morse Museum of American Art. Similarly, the Albin Polasek Museum & Sculpture Gardens is devoted to the work of its titular sculptor. Or, develop your own artistic talents with a course or two at the Crealdé School of Art.

Winter Park also hosts two annual, outdoor art shows. In March, the Winter Park Sidewalk Art Festival attracts more than 200 artists — and 350,000 guests — to Park Avenue and adjacent Central Park, while October's Winter Park Autumn Art Festival exclusively features Florida artists. Admission to both is free.

If live theater is more your thing, book a date at The Winter Park Playhouse. Just blocks from Park Avenue, the 123-seat venue is the only professional musical theater in Florida. And at Casa Feliz, you can enjoy live music and a tour of the historic home on Sunday afternoons.

Outdoors & Recreation in Winter Park

Winter Park's chain of lakes — 12 in all — includes 2,781 acres of pristine waterways, and the Winter Park Scenic Boat Tour is a fun, relaxing way to experience it. You'll see all manner of wildlife, not to mention multimillion-dollar mansions, during the narrated, one-hour excursions, which also go past Rollins College and Kraft Azalea Gardens.

Learn more: Orlando Sports, Recreation & Outdoors

The latter is one of 11 amenity-laden public parks maintained by the city, with other standouts including Mead Botanical Garden, Lake Baldwin Park, Phelps Park and Ward Park. And if seeing so much green has you aching for a tee time, don't worry: You can get your golf on at the Winter Park Golf Course, a 9-hole, public course that's on the U.S. National Registry of Historic Places.

With so much to see and do, it's no wonder why locals adore Winter Park — and why you should make it part of your travel plans the next time you're in Orlando!

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Written by Nate Shelton, Consumer Content Writer at Visit Orlando. He’s a native Floridian who appreciates the entertainment, historical and culinary aspects of Orlando and Orange County.

 

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Related Categories: Arts & Culture , Shopping , Sports, Recreation & Outdoors , Restaurants , Orlando for Adults

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