Seymour celebrated its sesquicentennial or 150th birthday on June 24, 2000, but Seymour's historical journey actually began in 1642, when land from the town of Derby extended into what, today, is Seymour.

The center of activity was where the Naugatuck and the Housatonic Rivers met in Derby. John Wakeman was the first European to purchase land from the Indians that lived throughout this area. He established a trading post at the Derby port where, eventually, tall sailing ships from many far-off ports came to trade. Within 13 years, several more settlers came to the area and the New Haven court granted permission for a village to be established on land purchased from the Indians