Park Avenue - Winter Park
Park Avenue in Winter Park is one of the most beautiful and walkable streets in Central Florida. This tree-lined boulevard runs along the shore of Central Park and features upscale boutiques, art galleries, restaurants, and the world-class Charles Hosmer Morse Museum of American Art. Winter Park is Orlando's most sophisticated suburb, founded as a winter retreat for wealthy Northerners in the 1880s.
Route Overview
The route follows Park Avenue from the Amtrak station south through the heart of Winter Park's shopping and dining district, past Central Park, and along the chain of lakes. Side streets lead to Rollins College, the Alfond Inn, and scenic lakefront neighborhoods with some of the most beautiful homes in Central Florida.
Stops Along the Way
1. Winter Park Farmers Market
Held every Saturday morning in Central Park West, this is one of the best farmers markets in Florida with local produce, artisan foods, flowers, and live music.
2. Charles Hosmer Morse Museum of American Art
Home to the world's most comprehensive collection of works by Louis Comfort Tiffany, including the stunning Tiffany Chapel from the 1893 World's Columbian Exposition.
3. Scenic Boat Tour
A one-hour pontoon boat cruise through Winter Park's chain of lakes and canals. The tour passes Rollins College, lakefront mansions, and lush tropical landscaping. Operating since 1938.
4. Rollins College Campus
Florida's oldest recognized college (1885) with a beautiful Spanish Mediterranean-style campus on the shore of Lake Virginia. The Cornell Fine Arts Museum on campus is free and open to the public.
5. Hannibal Square Heritage Center
A museum and community center celebrating the history of Winter Park's African American neighborhood. Exhibits feature oral histories, photographs, and artwork from the community.
Driving Tips
- Parking along Park Avenue is metered - bring quarters or use the ParkMobile app
- Free parking is available in the SunTrust garage and city garage behind the shops
- Park Avenue is one-way heading south - circle via New York Avenue to head back north
- Visit on a weekday for easier parking and a more relaxed shopping experience
Official Resources
Group Road Trip? BusBrother provides charter bus service along this route. Let a professional driver handle the road while your group enjoys the scenery. Get a free quote.