In May 1709, Wolcott was admitted to the bar and began to practice law. In 1711, during Queen Anne's War, He accompanied militia forces on an expedition to Quebec as a commissary. On his return he served as Clerk of the House, 1710-1711 and was elected Deputy to the colony's Lower House in 1709-1714, 1718, 1719, serving as Speaker in October, 1719. In 1714 he was elected to the Upper House (also called the Council) and served as Assistant, 1714-1718, 1720-1741, 1754-1760. He was Commissioner of Connecticut for the Adjustment of Colonial boundaries, 1717, 1718, 1723-1726, 1728, 1730, 1737, 1740, 1742, 1750. Captain of the Trainband of Windsor, 1722. Captain of Troops raised for active service, 1724. He was made judge of the Hartford County court in 1723, serving through 1732, and of the colony's Superior Court in 1732, serving through 1741. Wolcott was made Colonel of the First regiment, 1739.