Ridges separate one watershed from another.  Water drains down the hills into the streams in the valleys.  The streams continue to flow downhill toward sea level.
As you travel downstream, streams merge into larger streams. The water shed of a larger stream consists of all the smaller watersheds, or subwatersheds.

For example:
The land that drains into the Indian Rill creek is in the Indian Rill watershed.  The parking lot and floodplain meadow drain into Indian Rill as do the properties upstream of us all the way to Old Wilmington Road.  The Indian Rill Watershed and all of the other small watersheds from the other small creeks all  drain into the Red Clay Creek.  The Red Clay flows into the Christina River which is part of the Christina Watershed which is part of the bigger Piedmont Watershed (the watershed that includes the Red Clay, White Clay, Brandywine, Naamans, and Shellpot Creeks as well as the Christina).