The earliest recorded sighting of a Sea Serpent in North American waters was at Cape Ann in 1639. In 1817, reports spread throughout New England of a sea serpent sighted in Gloucester Harbor.
In 1639, the Colony ordered that a road be laid out from Boston to Portsmouth, to be constructed by each town along the way. The Bay Road made Ipswich an important stagecoach stop. Several milestones to indicate distances are still standing.
"Such small piggs as are pigged after the first of February shall have liberty to be about the towne, not being liable to pay any damage in house lotts or gardens, until the 16th of August next."