| Event | Date | Location |
|---|---|---|
| Unity Heritage Festival | January | Shady Park at Hannibal Square/New England Avenue |
| Park Avenue 5k | January | Park Avenue & Morse Boulevard |
| Run 4 Love | February | Showalter Field & Cady Way Trail area |
| Sidewalk Art Festival | March | Park Avenue (Lyman to Canton avenues) |
| St. Patrick's Day Parade | March | Park Avenue (Lyman to Canton avenues |
| Winter Park Road Race | March | Park Avenue & Central Park |
| Dinner on the Avenue | April | Park Avenue (Lyman Avenue to Lincoln Circle) |
| Run for the Trees 5k | April | Ward Park (Cady Way Trail > Loch Berry Road > Worthington Drive > Langholm Drive > Holts Grove Circle > Genius Drive) |
| 4th of July Celebration | July | Central Park (Park Avenue from Lyman Avenue to Morse Boulevard) |
| Watermelon 5k | July | Park Avenue (Swoope Avenue > New York Avenue > Beloit Avenue > North Pennsylvania Avenue > Summerland Avenue > Green Cove Road > Park Avenue > Palmer Avenue > Georgia Avenue > Interlachen Avenue > Welbourne Avenue) |
| Lady Track Shack | September | Mead Botanical Garden (Grover Avenue > Orchid Avenue > Denning Drive > Barnum Avenue > Minnesota Avenue > Azalea Lane > Pennsylvania Avenue > Fairfax Avenue > Essex Road > Oxford Road > Clarendon Avenue > Huntington Avenue > Maryland Avenue > McIntyre Avenue) |
| Fiddler's Green 5k | October | Mead Botanical Garden (Grover Avenue > Orchid Avenue > Denning Drive > Barnum Avenue > Minnesota Avenue > Azalea Lane > Pennsylvania Avenue > Fairfax Avenue > Essex Road > Oxford Road > Clarendon Avenue > Huntington Avenue > Maryland Avenue > McIntyre Avenue) |
| Winter Park High School Homecoming Parade | October | Park Avenue (Whipple to New England avenues) |
| Autumn Art Festival | November | Park Avenue (Lyman to Canton avenues) |
| Cows ’n Cabs | November | Morse Boulevard |
| Christmas in the Park | December | Central Park (Park Avenue from New England to Canton avenues) |
| Christmas Parade & Pancake Breakfast | December | New York (Canton to Webster avenues), Whipple Avenue, Swoope to Knowles avenues, Cole Avenue, and Park Avenue (Webster to Comstock avenues) |
| Winter on the Avenue | December | Park Avenue (Lyman to Canton avenues), Welbourne Avenue East, Morse Boulevard East and Lincoln Circle East |
Our Vision
Winter Park is the city of arts and culture, cherishing its traditional scale and charm while building a healthy and sustainable future for all generations.