Orlando's most walkable street
Park Avenue is the brick-paved main street of Winter Park — boutiques, galleries, cafes, and fine dining along one side, the green expanse of Central Park along the other, with the SunRail station dropping you right into it. The walking tours on this page keep using the same word: unhurried.
A winter retreat that stuck
The town began in 1881, when New England businessmen Loring Chase and Oliver Chapman bought the original 600 acres; it incorporated in 1887 and became a winter retreat for wealthy Northerners in the Ford and Edison era. One local-history walk on this page traces how that Gilded Age winter colony became one of Central Florida's most sought-after communities — the architecture never really changed its mind.
How to do the avenue
- Walk both ends — the Fairbanks/Aloma end bustles; the northern stretch quiets down
- Central Park is the living room — ice cream in the pavilion shade, people-watching between shops
- Parking turns over steadily during the day, per the local's tour — circle once before you give up
- It's dog- and kid-friendly in a way few Florida main streets bother to be
The calendar anchor
The events rundown on this page leads with the Winter Park Sidewalk Art Festival, one of the country's top outdoor art festivals, which takes over the avenue and the park. Even outside festival weeks, Park Avenue pairs naturally with the Scenic Boat Tour and the Morse Museum — Winter Park's complete day, all within a short walk.
Sources: the eight videos on this page — three full walking tours, a local's commentary walk, a realtor's block-by-block pass, and a sunset stroll — summarized from their entries in our catalog.