Winter Park & Park Avenue District

The City of Winter Park is one of Central Florida’s most visited communities in large part to the award-winning restaurants, sidewalk shopping, acclaimed arts and more in the upscale Park Avenue District. The city also has much for outdoor enthusiasts, including a robust parks system and the gorgeous Winter Park Chain of Lakes.

To really experience Winter Park, you will want to stick around for a few days. One of the best places to do so is The Alfond Inn. Owned by Rollins College, the recently renovated, AAA Four Diamond property boasts 112 guest rooms, a full range of amenities (including a pool) and a riveting art collection. Furthermore, the hotel’s profits endow a scholarship program at Rollins.

Shopaholics will adore Winter Park’s exquisite array of retailers, many of which are on and near Park Avenue. For instance, homegrown boutiques like Tuni Trendy + Chic and John Craig Clothier will have adults looking their best, while Tugboat & The Bird and Bebe’s and Liz’s will do the same for children. Or, go for bespoke designs at Big Frog Customs T-Shirts & More, just a short drive from Park Ave.

You will 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 The Ancient Olive Gourmet, Bang & Olufsen Winter Park, The Farmacy, Rifle Paper Co., 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.

Feed your inner artist at Winter Park’s galleries and museums, including Rollins Museum of Art, which offers free admission. This facility’s collection — more than 6,000 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.

Nearby, you can peruse the world’s most comprehensive 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.

The latter is adjacent to the Hannibal Square Heritage Center, where you can learn about its namesake Hannibal Square district’s origins as an important African American community. Officially founded in 1881, Hannibal Square was the site of one of the country’s earliest Civil Rights marches in 1887 and is now one of Winter Park’s most expensive sections.

If live theater is more your thing, book a date at The Winter Park Playhouse — one of the few professional musical theaters in Florida. And at Casa Feliz, you can enjoy the live Music at the Casa series on select nights. Alternately, take a tour of the historic home on Tuesdays, Wednesdays and Thursdays.
 

In addition to numerous holiday events, Winter Park hosts two annual, high-profile outdoor art shows. In March, the Winter Park Sidewalk Art Festival attracts more than 200 artists to Park Avenue and adjacent Central Park, while October’s Winter Park Autumn Art Festival exclusively features Florida artists. Admission to both is free.