Spanish moss, looking more like lacy gray-green holiday tinsel than tropical vegetation, hangs in graceful fringes from the live oak trees that form canopies over the brick-paved streets and canals of Winter Park. The trees, dressed with these moisture-fed trappings, are an iconic image that reflects the Old Southern charms and subtle elegance that define this charming and historic central Florida city.
Visitors to Winter Park, situated just north of Orlando, are drawn by the world-renowned annual festivals: one event that celebrates the music of Johann Sabastian Bach (1685-1750), or are attracted by the yearly Sidewalk Art Show, or come for an exhibition of collectible and rare automobiles at the Winter Park Concours d’Elegance.
Others come for its lakes, waterways, and health-giving springs, which is the reason why, when US President Chester A. Arthur visited in the 1880s, he declared it “the prettiest town in all of Florida.”

A rich, diverse culture
Winter Park’s first human residents were the migrant Muscogee people, Native Americans who eventually mingled with another Indian tribe — the Choctaw — to form an entirely new culture called the Seminole tribe.
The Seminole tribal region remained relatively unsettled until the 1880’s, when it experienced the first of many real estate booms as a result of the South Florida Railroad, which created a train line from Orlando to Tampa and Henry Flager eventually extended down to Key West.
The influx of visitors carried by the train also brought businesses, electrification, single-family homes, schools, and numerous hotels catering to “health tourists” in search of the curative powers said to be found in the region’s many lakes and mineral springs. A group of wealthy Boston businessmen weary of frigid New England winters created this exclusive lakeside housing development around six natural and man-made lakes, dubbing their creation, “Winter Park.”
The luxury hotels and health resorts that sprang up around the lakes at Winter Park also attracted many US presidents. The finest resort in Winter Park was the Langford Hotel (1950-1999). It drew many celebrity guests and entertainers, including Dean Martin, Frank Sinatra, Ray Charles, Eleanor Roosevelt, Larry King, Hugh Hefner, and John Denver. Now, on its place, sits the chic Alfond Inn.

Plying the waters of Winter Park’s famed lakes
To truly appreciate Winter Park, one must “take the waters,” or, more correctly, “take to the water” aboard one of the 18-passenger tour pontoon boats operated by Scenic Boat Tours (www.scenicboattours.com). Your narrator, who is also your able and amiable boat captain, will show you three of Winter Park’s six lakes during the one-hour tour. The lakes are connected by narrow, cypress-shaded canals that were hand-dug over a century ago by underemployed lumberjacks.
The lakes offer great views of the sprawling manicured backyards of the city’s wealthiest residents, and feature a private boat dock or an adjacent “floating garage” where boats are housed. The water views include a picturesque vista of Rollins College, and — who knows — you might sneak a peek at a gator or crane sunbathing along the mangroves as you pass through the narrow canals.

Celebrating its visual, lively arts and trendy restaurants
In addition to its lakes and waterways, Winter Park is well-known for its visual and lively arts, and trendy Park Avenue, lined with classy shops and delicious restaurants. Many restaurants offer a table near the sidewalk, which ensures a good observatory seat over the busy hustle of tourists and locals enjoying what is at hand. Near the center of Park Avenue you may catch the aroma of the rose gardens across the street and watch Amtrak trains deliver passengers in and out of the town depot, just a 38-minute train ride from Orlando.
Adjacent to the station is a brick building that was the original Winter Park train station; now offering meals on its breezy patio, stop there to enjoy their fresh sandwiches and vast assortment of homemade pastas and cheeses.
The Winter Park History Museum (http://www.wphistory.org) is at the other end of the old train depot, it now showcases the history of the city, and volunteers there will cheerfully set you up with a brochure for a self-guided Walking Tour of Winter Park’s Historic Sites — all 20 of them.
The Winter Park Farmer’s Market is worth getting up early to purview, located just two blocks west of Park Avenue. Farmers and locals food stalls offer everything from French croissants to fresh smoothies, local veggies and fragrant flowers.
The Florida Film Festival takes place each April at Winter Park’s own Enzian Theatre. On average, 170 films are shown during the ten days of this star-studded event.
It’s worth the short drive to enjoy a meal on the veranda of the Eden Bar, adjacent to the theater, sheltered under massive like oak trees; it features “one-of-kind ambience and fantastic menu specials.”
The Charles Hosmer Morse Museum of American Art, housed in a sprawling “California Spanish-style” building in the downtown shopping district, displays the world’s largest collection of art nouveau-style glassware, leaded glass windows, and decorative items created at the turn of the last century by the studios of Louis Comfort Tiffany.
The Tiffany works on display at the Morse Museum — stained glass windows, jewelry, enamels, mosaics, watercolors, and home furnishings — form the centerpiece of this massive, world famous collection. The Morse features an exact recreation of the stunning “Tiffany Chapel” that had been on display at the World’s Columbia Exhibition in Chicago in 1893. Other windows on display at the Morse were created by Tiffany’s on behalf of many noted 20th century designers, including William Morris, Louis Sullivan, and Frank Lloyd Wright.
Yearly, 78,000 visitors make the journey to the Morse Museum, the admission is a mere $5. The relatively low cost for the privilege of visiting this world-class museum is attributable, says Catherine Hinman, Director of Public Affairs, to “the beliefs of our founders, Jeannette and Hugh McKean. The museum admission price is a `benefaction,’ it is a gift to the community.”
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