This well-loved Nickelodeon/CTV series took on most of the great horror stories at one point or another - and they often did a pretty good job of it. They don't scare me much anymore, but when I was younger my friends and I tended to find them pretty spooky - we'd keep ourselves from getting scared by making fun of the episodes as we watched them. In particular, I remember that we used to keep track of how often they said "Sorry," with the good ol' Canadian "sore -ee" pronunciation. Thanks, CTV.
This one features a kid named Ian (who looks remarkably like a young Ichabod Crane) moving to modern-day sleepy hollow, where he's "initiated" into the town by going across the infamous bridge (here called "the Bridge of Souls") on Halloween night to retrieve the Headless Horseman's pumpkin head. He knows perfectly well that this isn't a real Halloween tradition, as the local gang of toughs (dressed as Pirates for Halloween) tell him, but he decides to do it anyway.
So off he ventures into the misty woods - woods are pretty generally misty in these shows - where he crosses the old bridge (which, in this version, isn't covered) and finds a jack-o-lantern, glowing green from a glow stick (maybe his saying "nice touch" here is a nod to the Garfield special, and maybe it isn't, but I prefer to think is is). Naturally, the bully jumps out with a scythe, scaring the bajeezus out of our intrepid hero.
Then, off in the distance, we see the REAL headless horseman. This is pretty standard business - most adaptations at least start out with Brom (or some other bully) dressing up as the horseman before the real one shows up.
Then, things get interesting. A pale-faced ghost of Ichabod Crane shows up, asking for directions. Back in town, the horseman shows up again, chasing Ian around. Initially, he assumes that it's just the bully again and goes for a confrontation, but, no, this is the real thing. They gave Ichabod directions, changing the story, and leading the horseman to look for a new victim. This leads to the titular midnight ride, in which Ian and his new girlfriend outrun the horseman on their bikes. The horseman vanishes in a really cool blaze of flames as Ian runs across the bridge.
One of the better minor adaptations, really.