I love collecting movies, shows and cartoons based on the classic story "The Legend of Sleepy Hollow". This episode of Wishbone and "Night of the Headless Horseman" are my two favorites in my collection, not that there's anything wrong with Bing Crosby's rendition, of course.
In this episode, the Jack Russell terrier with the vivid imagination is Ichabod Crane the school teacher from the Washington Irving classic. If you just judge this video in terms of Irving's original story, it is an above-average effort and faithful to the original but it might be too scary for children under 7.
This was originally broadcast in the fall of 1997 as a prime-time special in time for Halloween. The show tried to up the ante for their first hour-long effort and I think they succeeded admirably.
Again, this is one of my favorites. It definitely teaches kids about literature, and of course, having a cute little dog helps. Wishbone in The Legend of Sleepy Hollow also called Halloween Hound: The Legend of the Creepy Collars.