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Winter Park is an all-season gem just hours from Tampa Bay

The town offers a wide range of things to do without a big travel commitment.
Children play in a fountain in Central Park in Winter Park.
Children play in a fountain in Central Park in Winter Park. [ City of Winter Park Communications Department ]
Published Oct. 14

The posted speed limit for this posh town’s Park Avenue reads 20 mph. But locals and visitors to Winter Park both know it’s really stroll/browse.

A destination for most day-trippers, as well as locals, the avenue is lined with benches that invite passersby to pause under the shade of mature trees. More benches are just across the street, along the six blocks of Central Park.

Park Avenue in Winter Park is lined with restaurants and shops.
Park Avenue in Winter Park is lined with restaurants and shops. [ City of Winter Park Communications Department ]

Park Avenue and Central Park in a suburb of bustling Orlando? Chalk it up to the Northern millionaires who made this lake-framed village their winter home as the 19th century eased into the 20th.

Opposite the lush park it’s all commerce: art galleries, jewelers, financial advisors, a chocolatier and gelato shops, watch stores, women’s fashions — Chico’s to Lululemon to Lilly Pulitzer. Nonetheless, Park Avenue seems unhurried, graceful, full of sidewalk cafe tables with water bowls for the pooches. There are a few hidden grottoes separating the storefronts and offering a chance to meditate while sitting by koi ponds and shaded courtyard fountains.

What’s a stroll without a nosh, or a full meal? Restaurants along and near Park Avenue offer Turkish, Thai, French and Italian cuisine. There is much variety, from the cozy Omi, whose tiny kitchen turns out dozens of sushi and Asian cooked dishes, to the more-expansive — and expensive — AVA MediterrAegean, which has a cellar lounge for members only. A hallowed restaurant is Prato, which regularly changes about 75 percent of its Italian offerings.

Winter Park has many restaurants, featuring a variety of cuisines.
Winter Park has many restaurants, featuring a variety of cuisines. [ City of Winter Park Communications Department ]

Of course there is more to Winter Park than its high street. Museums distinguish this town of 31,000. At one end of Central Park is the Charles Hosmer Morse Museum of American Art, displaying the world’s most comprehensive collection of works by Art Nouveau master designer Louis Comfort Tiffany.

Less than a mile away, on the campus of Rollins College, is the Rollins Museum of Art. Its 5,600 pieces range from the Italian Renaissance to 21st century American art. A confirmation of the community’s appreciation for culture, the collection has largely been donated by friends of the museum and Rollins alumni. The museum also has 156 photographs and prints by Andy Warhol, donated by his foundation.

Winter Park originally was settled by farmers, orange growers and lumberjacks. The town’s first official structure, built in 1882, was its train depot — exactly what early developers needed to bring Northern visitors and land buyers to the lush area.

Much of the product of the local sawmills was used for fancy winter homes for the wealthy. Among them: Charles Hosmer Morse, a Chicago industrialist. He built his vacation home in 1904 and also bought hundreds of acres to be developed. Morse would go on to donate both land and money that created a golf course, University Club, Women’s Club, Central Park and, ultimately, the art museum bearing his name.

The Charles Hosmer Morse Museum of American Art in Winter Park has the world's most comprehensive collection of works by Louis Comfort Tiffany.
The Charles Hosmer Morse Museum of American Art in Winter Park has the world's most comprehensive collection of works by Louis Comfort Tiffany. [ THE CHARLES HOSMER MORSE MUSEUM OF AMERICAN ART | The Charles Hosmer Morris Museum of American Art ]
The Charles Hosmer Morse Museum of American Art in Winter Park has more than 5,500 pieces in its collection.
The Charles Hosmer Morse Museum of American Art in Winter Park has more than 5,500 pieces in its collection. [ The Charles Hosmer Morse Museum of American Art ]
The Charles Hosmer Morse Museum of American Art in Winter Park is on the campus of Rollins College.
The Charles Hosmer Morse Museum of American Art in Winter Park is on the campus of Rollins College. [ The Charles Hosmer Morse Museum of American Art in Winter Park i ]

Winter Park began to grow after World War II, and residents built enough stately homes that hundreds are listed on the town’s historical register. Over the decades, folks embraced conservation, and now parts or all of four districts are listed on the National Register of Historic Places.

One of the earliest prominent areas was Rollins College, which opened in 1885 and gently boasts that it was Florida’s first coed, four-year school of higher learning. Its tree-shaded campus borders Lake Virginia, part of Winter Park’s chain of lakes. You can use your own or rent canoes, kayaks and paddleboards. Local companies also sell guided tours on the water in daytime and at twilight.

If you’d rather leave the propulsion to someone else, step aboard the Scenic Boat Tour. You’re seated in a covered pontoon boat for a fun, even educational, 90-minute glide past some of the founding millionaires’ homes. Among them is the more modest place once occupied by Fred Rogers — yes, Mr. Rogers — bought for him by his parents when he was a music student at Rollins.

A canal leads to Lake Osceola, where visitors to Winter Park can take a scenic boat ride or rent kayaks and paddleboards.
A canal leads to Lake Osceola, where visitors to Winter Park can take a scenic boat ride or rent kayaks and paddleboards. [ City of Winter Park Communications Department ]

Winter Park also owns a flat, 9-hole public golf course. Dating to 1914 but updated just a few years ago, the par-35 course is tucked among homes, churches and the railroad tracks that service the station in — where else? — Central Park. To avoid heavily trafficked Interstate 4 from Orlando, visitors can board the commuter SunRail coaches at four locations around Orlando and stop off in Winter Park.

SunRail operates only on weekdays, but if you arrive on a Saturday, you can enjoy Winter Park’s vibrant Farm Market. Other major lures in Central Park are two acclaimed outdoor art festivals, in spring and fall.

Winter Park's Farm Market is a popular Saturday attraction.
Winter Park's Farm Market is a popular Saturday attraction. [ City of Winter Park Communications Department ]

Four short blocks west of the park is Hannibal Square, a vest-pocket shopping and dining district. Plan to spend a few minutes in the Heritage Center, which recounts the African American pioneers of Winter Park, and Rifle Paper Co., a trendy stationery manufacturer open to the public. And in a 10-minute drive from Central Park, you can be “in” with the smallest of in crowds by reserving space at the eight-seat Kadence. It’s a Japanese sushi restaurant whose New York and London trained chefs earned a Michelin star this year.

Though not the only reason to come to Winter Park, the Alfond Inn at Rollins is reason enough to spend the night. Named this year by Travel + Leisure as one of Florida’s top 15 resort hotels, the 112-room Alfond is owned by the college and net operating income goes toward a scholarship fund.

The inn’s walls display more than 400 pieces of art — textiles, oil, mylar, even ball bearings, all curated by the Rollins Museum and making the Alfond’s hallways an alluring diversion. Completion of a 71-room expansion and full spa addition is expected next spring, around the 10th anniversary of the original hotel’s opening.

Strolling hotel hallways, museum galleries, boutiques and bistros, or lake shore, Winter Park’s vibe recalls a time when walking was as fast as you needed to travel.

Robert N. Jenkins is former travel editor of the St. Petersburg Times.

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