2019 New Zealand Geographical Society There is little clarity as to which city is New Zealand's "oldest" or "first." Scholars, journalists, and websites make competing claims. This article examines various categories by which cities can claim to be oldest, and reveals that Auckland, Christchurch, and Wellington have valid claims but Dunedin and Nelson do not. Most claims are bound up in the inconsistent development of New Zealand's municipal authorities and representative institutions. I conclude that although the status of "oldest city" has no legal significance, this detail provides an accessible entry point to important historical narratives and to understanding urban life in colonial New Zealand.