Central Florida’s 2024 Best Main Streets Spotlight On Winter Park

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.