Cool, I think we're on the same page. I know what you mean by "orientation of the manifold along the path" but this isn't precisely the standard usage. (My vague memory is that you can define an orientation without needing a tangent space, but I can't think of an example, so could be wrong here.)
My background is in riemannian geometry so I never had to worry about lack of a tangent space. Certainly you can define orientability of some topological spaces that aren't even manifolds. I'd forgotten but you can even define a local orientation at a point for a general topological manifold in terms of it's top-dimensional homology. I think that's the most general situation it makes sense in, you need a well defined dimension to consider this.
