there’s a good chance that you’re going to visit one of my old school teachers, I grew up in Whitby and then in Goathland nearby. My mum works in the local comprehensive too.
Tbh, there’s isn’t much in Whitby itself. If you have a car, i’d recommend going to any of Goathland, Egton, Danby, Castleton, Hole of Horcum or Littlebeck. Also, there is some good riding at Cropton Forest, Rosedale Abbey, Langdale Forest and Dalby Forest. If you want to venture further north (middlesbrough way), then the area around Roseberry Topping looks fantastic (although i haven’t ridden around there). Most of those are rideable from Whitby itself, although the tourists are a menace on the roads and i would avoid if possible.
If you want any pub recommendations in whitby, i’d say that station inn and black horse are decent. The best pub in the area is the Birch Hall Inn in Beck Hole. The owners are great and the beer is brilliant. The locals are friendly and often down there which gives it a good vibe.