Located on the Quebec-Vermont border, the community was settled in the 1790s. The first family to arrive were the Taplins, who settled in 1796. The Taplins were like virtually every other pioneer family of that era. They came to Stanstead from New England. And they were looking for good land, which was becoming scarce in the new American republic.

The Taplins came to a country that was a complete wilderness. They were not alone for long, however, for they were soon followed by other families. The names of some of those families are still reflected in local place names: Pierce, Lee, Beebe, and others.

Stanstead was for some time an isolated backwater, the haunt of smugglers. A customs port was established here in 1821, the first in the Townships, and that helped. But some years later, officials were still complaining that Stanstead was “a community where smuggling is popular and the population is shrewd and lawless and ever willing to aid smugglers.” It is even said that some early pioneers made their fortunes smuggling.

Be that as it may, Stanstead blossomed in the 19th century. Growth and prosperity were everywhere. Where once there were forests were now wide streets with elegant homes, inns, and prosperous businesses. A major advantage to the economy was the stagecoach, which linked Quebec City and Montreal with Boston. So, early in its history, Stanstead took on the role of transportation centre, a role which, due to its strategic location on the border and its proximity to Autoroute 55, it retains to this day.