According to the classical perspective, polity size and democracy are inversely related. In this article, we argue that there is an important exception that manifests itself at the district level in settings where multiparty competition is allowed. Specifically, we find that larger districts encourage greater contestation. This results from a little-noticed mechanical effect as well as from several features of constituencies that are affected by size and have direct repercussions for contestation. To demonstrate this thesis we assembled a unique dataset, the Multi-level Election Archive (MLEA), which unites electoral contests across a variety of districts (national, regional, and local) and elective offices from the eighteenth century to the present, including a total of 88 countries, 2,344 elections, 79,658 districts, and more than 400,000 contests. With this evidence we were able to conduct a broad array of statistical tests, some global and others focused on particular countries or election types, all of which support our general argument.