Long Islanders love their Main Street attractions. From intimate restaurants to quaint theaters there is no shortage of excitement when it comes to trying the latest venture. The next time your travels take you South, three historic Central Florida towns (an easy drive from downtown Orlando), offer inspired architecture, cuisine from award-winning chefs and a host of cultural diversions similar to home. Plus, they’re all in pedestrian-friendly downtown locales.
Just 20 minutes northeast of Orlando, the city of Winter Park is home not only to Rollins College, a postcard-perfect chain of lakes and a train depot operating from one locale to another since 1890, it’s home to generations of families who settled in Orange County long before Disney opened its doors. Locals and tourists alike flock downtown to Park Avenue, which offers near-equal amounts of park and avenue, and the more recently revitalized Hannibal Square just two blocks to the west. Visitors will find familiar names such as Eileen Fisher and Lilly Pulitzer among the awnings, as well as independent retailers, a Saturday farmer’s market and award-winning restaurants like LUMA on Park and Prato, both run by James Beard Award finalist Chef Brandon McGlamery.
While the annual Mount Dora Arts Festival has wooed art enthusiasts for more than 40 years, dozens of small galleries, antique shops and studios give this charming lakeside town an artsy feel all year round. The newest addition to the area, 1921 by Norman Van Aken, marries art and cuisine with modern Florida flair. James Beard Award winner Van Aken has crafted a relaxed and refined menu heavy on Florida seafood and produce, and the converted home the restaurant occupies is filled with pieces on loan from the Modernism Museum across the street. For those who look to the outdoors for their art fix, boat tours of Lake Dora and the Dora Canal depart several times daily from the docks on 4th Avenue and in front of Lakeside Inn.
The 22-mile West Orange Trail is a favorite among area cyclists, and on a sunny weekend it can seem as if nearly all of them have made a pit stop on Winter Garden’s brick-lined Plant Street, and who could blame them? The restored 30s-era Roper Garden building houses a theater (the Garden), a martini bar (Pilar’s) and a restaurant showcasing seasonal scratch cuisine (Market to Table). At nearby Plant St. Market, craft beer enthusiasts can enjoy the onsite offerings of
Crooked Can Brewery and order laid-back bites from the Market’s other tenants to enjoy indoors or out.