This is the big one on Sydney's run calendar. Whether you’re a serious runner, jogger, walker, pusher or want to join in for the first time, don’t miss your chance to cry on the way up Heartbreak Hill. There are 80,000 participants each year and entries for City2Surf are open now. You'll want to start training soon – the hills are a bitch and 14km can feel much longer than it sounds.
If you’re a newbie to Sydney’s running scene, you probably need the low down on the course. You’ll start the friendly run with all the fancy dress folk and serious sprinters at Hyde Park, and call it quits at Bondi Beach. You’ll start on the downhill and feel like you’re going to crush it, then probably hit a wall in Rose Bay at the aforementioned tear jerking Heartbreak Hill. Once you reach Vaucluse, you’ll be seeing salty blue views all the way till Bondi. It’s a stunner of a race.