Ian Matthews Appeared as a main character in the epiosde "The Tale of the Midnight Ride". He was portrayed by Tighe Swanson.
Ian is a nice, sweet, charming and helpful person. He and his family had just recently moved to the town of Sleepy Hollow before the eve
nts of the story took place. He was new and he was trying his best to make new friends and to fit in.
Then during Hallowe'en time, he met a nice and kind young woman named Katie. He and her developed an immediate charm for each other after and agreed to dance together at the upcoming Hallowe'en dance. Also he had a problem: Brad.
Brad was Katie's jealous and possessive ex-boyfriend who kept stalking and harrassing her and threatening to harm any other guy who took an interest in her. But he wasn't afraid, he was more than willing to stand up for himself. He nicely helped Katie set up the decorations for the dance and he and her spoke and got to know each other a little better.
Then at the night of the Hallowe'en dance he and her both came wearing very similar costumes. He and her hit it off and had a fun time dancing and socializing. Also a bunch more of his classmates got to know him to and begun to really like him too. That is everyone except for Brad. Brad was jealous of his attention and jealous of Katie. He stood up for Katie telling him she didn't want to speak to him. Then Brad and his friends dragged him and her outside.
There he put his fists and was prepared to fight and defend himself. When surprisingly Brad calmly revealed that he did not want to fight him. Brad instead wanted him to take the Sleepy Hollow initiation test. The test that every new person in there town has to take. He had to go to the bridge of souls, and bring back the Headless Horseman's pumpkin. If could do this, then Brad promised that he and his friends would leave him alone. If he couldn't do it, then he and Brad would fight for real.
He went over to the bridge and found the pumpkin, thinking it was a simple thing to do. Then suddenly the Headless Horseman appeared preparing to attack him with his cutlass. Ian cowered in fear and cried and screamed begging him not to cut off his head. Then suddenly the costume came off to reveal it was Brad playing a joke. Then Brad and just about everyone else was laughing at him making him feel like a humiliated loser now. However Katie stayed by his side and didn't abandon him.
Then he lent Katie his Jacket and nicely walked her home. Along the way, he and her encountered the ghost of Ichabod Crane. He nicely asked him and her for directions to the bridge of souls. Ian and Katie nicely told him to take the left turn. Then after he walked her home he went back to school to get his bike. Then he remembered his keys were in his jacket pocket. So just as he was about to return to Katie's house. Then she appeared on her bike to return his keys to him.
Then just as he Katie were about to start riding back her they heard a loud laughing sound and horse hooves. He was fed up thinking it was Brad again. So he yelled out to Brad to leave her alone, and reminded him that she didn't like him anymore. Also that if they wanted to fight then they will. When suddenly a shadow on the side wall of the school reveals itself to be the real Headless Horseman. and it begun to chase them.
They soon figured out that it was now after them because they made a mistake. They accidentally gave Ichabod Crane the correction direction to safety. So the legend was altered, and the horseman was now chasing after him and Katie. So he and Katie rode their bikes as fast as they could. At first Ian picked up a pumpkin thinking the legend of the story could work both ways. So he tried throwing a pumpkin at it. But it just caught it instead and was unharmed.
Ian and Kate finally found the bridge of souls. the Headless Horseman burst into flames and vanished as it was taunted to cross it to attack him. Katie panicked for a moment thinking he got caught in the flames too. Then she was relieved to find out that he jumped off of it just in time.
Afterwards he and Katie meet up with Ichabod Crane again. He told them that once again he was lost his way and he thinks it is better to go the right way (the wrong way actually). He and Katie knew that he needed to accept his fate and told him that he was better to do so.