Robin is an optimistic, country-bred eighteen-year-old son of a clergyman. Seeking to make his start in the world, he arrives in Boston hoping his wealthy relative will help establish him. He is naive but possesses a strong sense of civility and personal restraint, often relying on his oak cudgel for a sense of security while wandering the unwelcoming streets.

Major Molineux is Robin's older relative who previously visited Robin's country home. He is a prominent figure affiliated with the British Crown, and Robin believes him to be highly respected, rich, and well-connected in Boston's high society.

The Horned Man is a fierce, menacing figure whose forehead bulges into a double prominence and whose eyes glow like fire in a cave. He is a dark, rebellious presence in Boston who strikes fear into Robin and seems closely tied to the city's chaotic undercurrents.

The Old Man is an elegantly dressed Bostonian who speaks with a peculiar, ghastly "hem" that sounds like a cough from the grave. He represents Robin's first taste of the city's rudeness, quickly becoming annoyed and threatening the young man with the stocks when asked for assistance.

The Innkeeper manages a sociable but rough establishment frequented by seafarers. He initially treats Robin with courteous flattery, assuming the young man's connections imply wealth, but he rapidly turns insulting and aggressive upon learning Robin has no money.

This small, slender woman attempts to lure Robin into her home using flattery. She represents the sinful temptations of the big city, providing a sharp contrast to Robin's pure, rural upbringing.

The Friendly Stranger acts as a comforting presence for Robin in the middle of a chaotic and unfriendly night. Well-connected in Boston and perceptive of Robin's rural innocence, he shows genuine compassion to the lost youth.

The Ferryman transports Robin to Boston late at night for an extra fare. He observes the young man closely, noting his well-worn but well-made country clothing and lack of worldly wealth.

Robin's father is a rural clergyman and farmer. He struggles financially but maintains a pious household, hoping that his familial connection to Major Molineux will secure a better future for his younger son.