1. Recall that the Headless Horseman is only one-fourth of the problem in this incarnation of the Sleepy Hollow legend.
2. Headless is also the reanimated body of Abraham, Ichabod's ex best friend and former suitor of Katrina, Ichabod's wife.
Yep, that's the same dude. Figures that Ichabod personally knows Headless. He apparently knows everybody from his time period.
3. Case and point: Ichabod offhandedly mentioned that he used to date Betsy Ross.
4. And Ichabod used his personal knowledge of George Washington's habits to help Abbie find a map to purgatory.
5. Katrina was finally rescued and brought into the present time period!
6. But Abbie had to stay behind in purgatory to take Katrina's place.
"Still not bothered" — the shippers