Park Avenue is one of the most walkable main streets in the state.

Park Avenue

Designed around a central park and its main street, Park Avenue, Winter Park was born as a “wintering” destination for wealthy Northerners and became the first planned community in Florida when it was chartered in 1887. That same year, construction began on the Orlando and Winter Park Railroad, which brought affluent tourists to Central Park, at the heart of Park Avenue. Among those first travelers to Winter Park were presidents Grover Cleveland and Benjamin Harrison. 

Today, the Winter Park Station serves SunRail and Amtrak commuters, and the park is host to a vibrant farmers market. 

The expansive tree canopy, bricked streets and plentiful benches are but a few of the amenities you’ll find not only on Park Avenue, but throughout Winter Park. 

Shop ‘Til You Drop

The elegant feel of a stroll down Park Avenue is still a big draw today. Families, couples, groups of friends and singles can all be found taking a leisurely jaunt or bike ride through the mix of local and popular chain boutiques. Lilly Pulitzer, lululemon, Chico’s and Warby Parker can all be found here, mixed in among independents Writer’s Block Bookstore, Through the Looking Glass and Frank.

Just steps from Park Avenue is the Rifle Paper Co. flagship, whose designs can be found throughout Florida and at Winter Park’s own Alfond Inn (more on that later). Barnie’s Coffee & Tea Co. was also founded in Winter Park and was a pioneer in sourcing high-quality fair-trade coffee beans from around the world. In addition to its lauded coffee creations, Barnie’s offers a lengthy menu of breakfast and brunch selections.

Jewelry stores are plentiful here, and shoppers will find a great variety of styles to suit every fancy. Be On Park specializes in bright, bold and playful selections. Jewelers on the Park specializes in estate jewelry, watches, jewelry repair and is an exclusive authorized dealer of the Jennifer Lopez collection by Endless. Reynolds Jewelers, founded in 1974, is known for its excellence in customer service and for its fine and custom pieces. 

It’s easy to make a day of it on Park Avenue. Take a guided tour at the Charles Hosmer Morse Museum of American Art, home to the most comprehensive collection of works by Louis Comfort Tiffany, then follow it up with Italian cuisine at Prato.

Marvelous Museums

Winter Park is also a museophile’s paradise. Anchoring the north end of Park Avenue is the Charles Hosmer Morse Museum of American Art, home to the most comprehensive collection of works by American designer and artist Louis Comfort Tiffany. 

Originally trained as a painter, Tiffany developed a new method of glassmaking after studying the chemistry and the techniques of glassmaking when he was just 24 years old. In 1881, he patented his method of creating an opalescent window glass, then considered a radical new treatment. Today, his designs are among art’s most iconic. 

The Morse Museum’s impressive collection includes Tiffany’s jewelry, pottery, paintings, art glass, leaded-glass lamps and windows, his chapel interior from the 1893 World’s Columbian Exposition in Chicago and architectural objects from his Long Island estate, Laurelton Hall. 

A few blocks away, the Hannibal Square Heritage Center is a tribute to the past, present and future contributions of Winter Park’s African American community. Established by the Crealdé School of Art, the center’s permanent exhibit features more than 200 archival pieces that document significant local and national events in African American history since the Emancipation Proclamation. It also offers a rotating series of public art installations and education programs that explore Black heritage and cultural preservation. 

Once home to the Winter Park Railroad, the Park Avenue station today serves SunRail and Amtrak commuters.

The Rollins Connection

Also within walking distance of Park Avenue is Rollins Collins, the oldest college in Florida. It was founded in 1885 by New England Congregationalists who brought their style of liberal arts education to Florida. 

Consistently ranked as one of America’s best colleges by the U.S. News & World Report, Rollins has produced Rhodes, Fulbright, Goldwater and Truman scholars. But perhaps its most famous alum is a man who taught children life lessons through the “Neighborhood of Make-Believe.” 

Yes, Fred Rogers graduated from Rollins in 1951, after transferring from Dartmouth. A sculpture that captures his love of teaching (and the characters from “Mister Rogers’ Neighborhood”) can be found on campus, part of a self-guided walking tour.  

Another landmark Rollins connection is The Alfond Inn, a boutique hotel situated between the college and Park Avenue. You’ll find contemporary art around every corner at this chic resort (its pieces come from the Rollins Museum); it makes imaginative use of Rollins’ school colors: blue and gold, soothing shades you’ll also find throughout the hotel. 

The elegant respite has 112 guestrooms and suites, a new café and spa, fine dining at Hamilton’s Kitchen and a concierge to assist with travel plans and reservations. 

And here’s something you can feel great about: All operating profits from The Alfond Inn endow The Alfond Scholars program at Rollins.

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