Winter Park Information

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Just minutes north of downtown Orlando lies the beautiful Winter Park. Often mistaken as part of Orlando, it is in fact it's own city. Winter Park offers an escape from the theme parks and city life into a peaceful town of fine wine and dining, quiet evenings, beautiful homes and parks, and great shopping. Perfect for family outings, romantic nights, or an upscale night out with friends, Winter Park is a place frequented by locals who simply can't get enough of the beauty of the area, and is easily a favorite spot of ours.

Historic Winter Park

Winter Park began to develop in the mid 1800s after the construction of a railroad between Orlando and Sanford. Before it was a city, the area grew to become home to a few landowners and even a post office. In the late 1850s, however, a pair of northern investors began purchasing large tracts of land with the idea of developing the city of Winter Park, which wasn't named for its' first 20 years of existence. Over the course of a few years they designed the layout of the city, began building streets, and opened numerous shops and stores to begin the initial formation of the city. In order for others to build within the city they had to follow strict architectural requirements that made sure the city was created in the light of the founders. To this day, some of the original buildings still stand along the brick lined streets of Winter Park.

What Does Winter Park Have to Offer?

Aside from the quaintness and beauty of the area and its many lakes, Winter Park also offers a cultural departure from the tourism areas of Greater Orlando. Old homes and buildings can be seen at almost every turn, along with modern shopping and dining to compliment the area. Winter Park is also home to 75 city parks that are spread throughout the nine square miles that represent the city. Here is a short list of suggestions that we have put together for things you might want to see in Winter Park.

Park Avenue - Park Avenue is the main street in downtown Winter Park, and it is along this street that visitors can indulge in top notch shopping, dining, and relaxation. Park Avenue is famous for its brick streets lined with live oaks and mixtures of modern and historic architecture. Along Park Avenue visitors can also find Winter Park's Central Park, which is a nice area for afternoon walks or picnics.

Rollins College - Rollins College was the first four year university in the state of Florida. Visitors can walk the grounds of the lakeside campus and take in some of the earliest buildings in the area. The Rollins campus, much like the rest of Winter Park, is a mixture of old and new and, with its convenient location just off of Park Avenue, is an easy departure from any day in Winter Park.

Bach Festival - Each March Winter Park holds their famous Bach Festival, a festival dedicated to the life of the famous composer, Johann Sabastian Bach. After over 85 years of the annual celebration, it has garnered worldwide attention, as one of the premier Bach Festivals in the world, and in the nation. Each year the festival invites talented musicians from around the world to come and recreate some of Bach's most famous works. In addition to the month long festival, concerts are held throughout the year by the organization. For more information you can visit the Bach Festival website.

Winter Park Sidewalk Art Festival - Held in Winter Park each March, the Winter Park Sidewalk Art Festival has gained national attention, drawing over 350,000 visitors each year, and hosting over 250 artists from around the world. The festival takes place just off of Park Avenue in Central Park and features photography, painting, jewelry, ceramics, and much more. Many of the items shown are for sale at the festival. You can find more information online at the festival website.

Winter Park Concours d' Elegance - Every November Winter Park hosts the Concours d' Elegance, which is an exotic car show that takes over the streets of downtown Winter Park. Featuring some of the rarest cars from around the world, car enthusiasts and curious patrons alike will be fascinated by the range of modern and old cars on show at the festival. For more information you can visit the festival website.

Weekly Winter Park Farmer's Market - Each Saturday the city of Winter Park holds a large farmer's market just off of the main drag on the old city railroad depot. Hundreds of different booths are set up to sell and give out samples of a number of home grown produce and plant products as well as an endless supply of baked goods. Dozens of food options are also available throughout the market. The stalls are open from 7am to 1pm each Saturday, making this a great way to start your day, and one of our favorite ways to spend time in Winter Park. For more information you can visit the Winter Park website or our Farmers Market guide.

In addition to these great places and festivals, Winter Park has plenty of every day offerings of great shopping, dining, and drinking. Here are a few links that will help you get on your way with your time in Winter Park.

How Much Time Should I Spend There?

Similarly to downtown Orlando, it is very easy to spend an entire day (or more) exploring the riches and beauty of the Winter Park area. If you are pressed for time, however, a stop in Winter Park can easily be combined with visits to other surrounding areas including downtown Orlando or any of the nearby nature reserves just north of Orlando. Walking and shopping down Park Avenue can be a day within itself, but an afternoon would also suffice. If time allows, we highly suggest simply hopping in your car and driving around the beautiful neighborhoods in the Winter Park area. Here you will see century old homes on brick streets lined with century old live oak trees. It is easy to imagine what the area might have looked like not too long ago.

If you have any concerns or questions about your visit to Winter Park, please feel free to contact us, and we will do our best to help you find an answer.

Photo Credits: Chad Miller - Outdoor Movie in Winter Park (photo 1)