Ichabod Crane, was a good-hearted, friendly and caring person. Some time shortly after the American Revolutionary War ended, Ichabod Crane moved to the town of Sleepy Hollow, where he applied for the job as the new Schoolmaster. He was well informed that the town's woods were haunted and it was very dangerous to be out in the woods late at night. Because the ghost of The Headless Horseman was riding around searching to prey on innocent victims.
He was very religious and very well educated and he knew that on his way home was a specific bridge called The Bridge of Souls. A sacred and holy bridge, that only good and purity could cross, not the forces of evil, if they did it would destroy them.
One night he was out too late, when he rode back home on his horse he got lost at a fork in the road, and took the wrong turn. Therefore he never found and passed the Bridge of Souls. The Headless Horseman, spotted him and chased him down and throwing his evil magical Jack-o'-lantern pumpkin at him Killing him.
Every Hallowe'en in Sleepy Hollow since then, a curse of some sort caused the events of that night to take place all over again. Ichabod would still be looking for the Bridge of Souls to make it safely back home, and The Headless Horseman would reappear again riding through the woods searching for victims.
One night in the 1990s, while riding his horse he bumped into Ian Matthews and his friend Katie. He was very polite and friendly to them and expressed his concern of seeing young children out so late at night and especially on Hallowe'en of all nights. He nicely told them he was lost and and asked for directions to the Bridge of Souls. Ian Matthews and Katie, not knowing who he was at first accidentally gave Ichabod Crane the correct instructions to the Bridge of Souls telling him to go to the left. Ichabod politely thanked them and went on his way and he introduced himself by name and said he was the new schoolmaster. So he safely found his way back home.
The story was then accidentally changed and altered and he was never a hunted down victim of The Headless Horseman. Ian and Katie took his place. to correct the mistake Ian and Katie played the story out until they were safe crossing the Bridge of Souls.
Afterwards he meets with Ian and Katie again. He tells them that once again he's lost his way and he thinks he's better to go the right way (the wrong way actually). Ian and Katie knowing that he needs to accept his fate tells him he's better to do so. He leaves telling them goodbye, Happy Hallowe'en and to watch out for The Headless Horseman!. Unaware that he would be encountering him anytime now.
- Arthur Holden also portrayed Mr. Brooks in "The Tale of the Dead Man's Float" and The Court Jester.