| Event | Date | Location |
|---|---|---|
| Annual Unity Heritage Festival | January | 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) |
| St. Patrick's Day Parade | March | Park Avenue (Lyman to Canton) |
| Winter Park Road Race | March | Park Avenue & Central Park |
| Dinner on the Avenue | April | Park Avenue (Lyman to Lincoln) |
| Run for the Trees 5k | April | Cady Way > Loch Berry > Worthington > Langholm > Holts Grove > Genius |
| 4th of July Festival | July | Central Park (Park Avenue from Lyman to Canton) |
| Watermelon 5k | July | Park Avenue (Swoope > New York > Beloit > N. Pennsylvania > Summerland > Green Cove > Park Ave > Palmer > Georgia > Interlachen > Welbourne) |
| Lady Track Shack | September | Mead Botanical Garden (Grover > Orchid > Denning > Barnum > Minnesota > Azalea > Pennsylvania > Fairfax > Essex > Oxford > Clarendon > Huntington > Maryland > McIntyre) |
| Autumn Art Festival | October | Park Avenue (Lyman to Canton) |
| Fiddler's 5k | October | Mead Botanical Garden (Grover > Orchid > Denning > Barnum > Minnesota > Azalea > Pennsylvania > Fairfax > Essex > Oxford > Clarendon > Huntington > Maryland > McIntyre) |
| Winter Park High School Homecoming Parade | October | Park Avenue (Whipple to New England) |
| Cows ’n Cabs | November | Morse Boulevard |
| Annual Christmas in the Park | December | Central Park (Park Avenue from New England to Canton) |
| Christmas Parade & Pancake Breakfast | December | New York (Canton to Webster), Whipple Avenue, Swoope to Knowles, Cole, and Park Avenue (Webster to Comstock) |
| Parade of Bands | December | Park Avenue |
| Winter on the Avenue | December | Park Avenue (Lyman to Canton), Welbourne East, Morse East and Lincoln 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.