Tom is a thirteen-year-old boy living in a small Midwestern town. He acts as the unofficial leader of a tight-knit neighborhood friend group. Highly observant, he actively questions his surroundings and pushes his peers to explore the mysterious old house by the ravine. His choice to wear a skeleton costume reflects a natural curiosity about the darker elements of the holiday.

Joe, commonly called Pipkin by his friends, is an energetic and mischievous boy whom his peers view as the greatest boy in their town. Usually fast and carefree, his sudden physical illness on Halloween night causes immense distress among the group. He instructs his friends to go ahead without him, promising to catch up later. His absence creates a noticeable void in the holiday traditions for the rest of the boys.

Carapace Clavicle Moundshroud is a tall, skeletal figure with a pale face and pinpoints of green fire for eyes. He lives in a Victorian Gothic house situated near the town's ravine, where he maintains an enormous tree covered in illuminated jack-o'-lanterns. Acting as an eccentric teacher, he challenges the boys to understand the history of their costumes. He leads them on a magical flight through time to search for their missing friend.

Ralph is a member of the local group of boys traveling through the town on Halloween night. He dresses in a mummy costume for the holiday, an outfit he wears without fully understanding its historical origins. He sticks closely to the group as they search for Pipkin and confront the strange occurrences at the ravine.

J.J. is one of the young boys participating in the group's search for Pipkin. He wears an apeman costume, linking him visually to early human history. He travels as part of the collective pack, sharing their confusion and awe when they encounter the Halloween Tree.

Hackles is part of the energetic group of boys roaming the small Midwestern town. He dresses as the Grim Reaper, complete with a miniature scythe. Like the others, he is deeply unsettled by Pipkin's sudden illness and relies on the strength of the group to face the strange events at Moundshroud's house.

Henry-Hank is a young boy in Tom's neighborhood circle. His choice to wear a witch costume for Halloween adds to the variety of historical figures represented by the group. He shares the collective anxiety over Pipkin's condition and participates in the magical flight to locate him.

Wally is one of the local boys setting out on the Halloween journey. Clad in a gargoyle costume, he travels alongside Tom and the others to the haunted house. He provides support to the group as they encounter supernatural forces in their attempt to help Pipkin.

Fred is a member of the tight-knit group of friends traveling through the Halloween night. He dresses as a beggar, participating in the modern tradition of trick-or-treating while unknowingly echoing ancient customs. He follows Moundshroud's directions to help rescue their missing friend.

George is one of the neighborhood boys caught up in the Halloween adventure. Wearing a ghost costume, he embodies a classic symbol of the holiday. He works alongside the other boys to build a kite and follow Moundshroud into the unknown.