2018 People’s Choice Winner: Downtown Winter Garden

Meet Downtown Winter Garden

The Historic Downtown is listed on the National Register of Historic Places and is a favorite destination for West Orange County residentsand those who travel the award- winning West Orange Trail. In 1992, the Downtown Community Redevelopment Agency established strategic outdoor areas to create energy and activity along the main corridor – West Plant Street. This started with the bike trail, the West Orange Trail, which is soon to be part of the 250-mile continuously paved multi-use Coast-to-Coast Connector. The trail segment that runs directly through the middle of Downtown was developed as a linear park on land formerly used as a railway. 

The Downtown route is pedestrian-friendly and provides an “outdoor living room” feel, featuring the City Clock Tower, Centennial Plaza Fountain, a gazebo with benches, and swings: all elements that help create an outdoor environment that is constantly filled with people and energy. A parking garage was recently constructed in Downtown to provide hundreds of free parking spaces to both residents and visitors.

Regional amenities that are popular include the Garden Theatre, the SoBo Art Gallery, historic icons, boutique shops, restaurants, museums, and the Pavilion which is home to the Splash Park, the Winter Garden Farmers Market, and a plethora of micro events held throughout the year. Open every Saturday, the Farmers Market is a regional farmers market and has been recognized nationally year after year. The Blues and BBQ festival pairs the hottest Blues and Roots musicians with award-winning local BBQ connoisseurs, creating incredible energy when the smooth sounds of blues and barbecue fill the air. Downtown is an urban garden with colorful planters, landscaping and lots of trees.

This is an integral part of Winter Garden’s heritage and name. When you visit, the buildings and streets are softened by the green landscaping. Known for brick mercantile buildings and masonry vernacular storefronts with varied colors and facades, Downtown Winter Garden exudes a perfect blend of warmth and energy, leaving you with a feeling that you truly are experiencing a great place!