The upscale village of Winter Park is full of historical and top cultural attractions just north of downtown Orlando. From a 9-hole golf course and sophisticated shopping boutiques to fancy restaurants and Florida's first college, there are so many things to see and do in Winter Park Orlando.

    You can visit this quaint area in the day for a spot of lunch and shopping, but most people choose to come in the evening when the main street is lit up and a pleasant vibe sees many couples out for a stroll after dinner and drinks.

    Winter Park Orlando - one of the highlights of 52 Best Things to Do in Orlando (Read all about Orlando here)

    photo by Joe Shlabotnik (CC BY 2.0) modified

    The historical neighbourhood was developed in the late 19th century and much of the original architecture still remains, such as Rollin's College, the first 4-year college in the state of Florida. Winter Park is also famous for its cultural festivals, including the Sidewalk Art Festival, which has taken place annually in the area for over 50 years. The festival features some of the world's best artists and is one of the oldest and largest outdoor art festivals in the United States.

    photo by Joe Shlabotnik (CC BY 2.0) modified

    The village has a 9-hole golf course, which is listed on the National Register of Historic Places. Walk along Park Avenue and you'll come across plenty of other cultural hotspots, including the Charles Hosmer Morse Museum and the Cornell Fine Arts Museum.

    Parking on the streets of Winter Park can be a little bit difficult at weekends. It's best to park at the Park Place Garage or at the free all-day parking lot on New York Avenue.

    photo by Ebyabe (CC BY-SA 3.0) modified

    Winter Park Orlando

    Location: Winter Park, Orlando, FL 37292, USA

    Ari Gunadi | Compulsive Traveller

    Start planning your trip

    Keep exploring


    United States of America

    COVID-19 Travel Alert

    Attractions and experiences recommended in our guides may be affected. Please check local guidance before you travel.

    Back to top