255 S. Denning Drive, Winter Park
Climbing is hard in flat-as-a-pancake Orlando – children resort to bookshelves, countertops, grandparents. Of all the playground equipment around the city, Denning Park’s Community Playground offers a grandly huge, labyrinthine wooden contraption on soft, non-ouchy mulch. It’s custom-designed, rather than a brand-name prefab made of ugly plastic and sizzling-hot steel tubes, and has a shaggy, premodern appearance (though the city of Winter Park has sanded down the splinters and edges). Sheltered by marvelous shady oaks, parents can lounge at picnic tables while the city’s youngest adventurers explore a fascinating, sometimes tunnel-like, three-dimensional space. Best part: It’s free.