Oakleigh can be visited at any time of year — the cafes and restaurants on Eaton Mall operate year-round and the outdoor tables fill up in all seasons. That said, a few times are particularly worth knowing about.
Weekend evenings from Thursday through Saturday are when the precinct is most alive, with the largest crowds, the longest queues at the souvlaki shops, and the most festive atmosphere on Eaton Mall. If you want to see Oakleigh at its best, arrive around 7pm on a Friday or Saturday.
Greek Easter, which falls in spring (typically April or May), is a significant occasion in Oakleigh. The community celebrations and the special foods — lamb on the spit, tsoureki (sweet Easter bread), red-dyed eggs — are visible around the precinct in the days before Easter. The suburb has a different energy in this period that is worth experiencing if you happen to be in Melbourne.
The spring racing carnival in October and November brings race-day crowds to nearby Caulfield Racecourse. This does not significantly affect the Oakleigh dining precinct but adds an additional reason to be in the area on a major race day.