The Oakland Castle Oakland, NJ – Hike into History Take a hike. Depending on your tone of voice it can be good advice or a condescending suggestion. In this case it is very good advice because Oakland offers its residents a great opportunity to enjoy outdoor exercise, take in some beautiful scenery, and wander down wooded paths that lead you through local, regional and world history. The hike detailed here starts just off Skyline Drive and is approximately five miles, start to finish. It will take you up through the Ramapo Hills to great vistas where you can visit the ruins of what has been called “The Oakland Castle”, “The Van…