Founded in 1634 by John Oldham, Wethersfield CT is the oldest settlement in Connecticut according to the Code of 1650 which refers to Wethersfield as “Ye Most Auncient Towne” in Connecticut. Wethersfield is a wonderful blend of the old and the new. The historic district, “Old Wethersfield”, is an authentic and living museum and the largest histroic area in Connecticut. However, Windsor, CT also lays claim to being the oldest town in CT. How can two towns claim to being the oldest town? Windsor was the first English trading post, settled in 1633, by Plymouth Colony.