George Overin (Caleb Brewster) was a natural fit for his role as he's well-known for playing the swashbuckling fiend Monte in the Ye Pyrate Brotherhood. His character Caleb Brewster as often been described as a "patriotic pirate" with a "beautiful disregard for the rules". In addition George also plays beloved chimney sweep each year during the Port Jefferson Charles Dickens Festival.
Jeannie Goldstein (Spy) plays the unnamed protagonist who represents the audience's point of view throughout the Culper Spy Adventure. Her character is assumed to be male but is actually a homage to the mysterious Agent 355, a female spy, who was never identified or may have never actually existed in the first place.
Three generations of the Overin family participated in the making the Culper Spy Adventure.