Holdsworth Street Playground

One of the better spots in Woollahra for the under-5 crowd — it’s fully enclosed, which makes a huge difference when you’ve got a bolter on your hands. There’s solid shade coverage, so you’re not baking on a bench while the kids work through the slides and swings. Picnic tables and restrooms on-site mean it actually works for a birthday party without too much extra effort. The local playgroup scene here is pretty active, so if you’re new to the area, it’s a genuinely easy place to meet other parents.