Bob’s overlook trail is located in the Catoctin State park. There is a parking lot right inside the main entrance. The trail starts near the parking lot and goes straight up. We hiked this in July (the first time) and it was a hot and miserable climb. At the top of the trail is a split that goes at right angles from the trail. One trail goes to the East lookout and the other goes to the West lookout. They are both short hikes to the lookouts.
After the lookouts, you’ll see more trail. This is the flat trail on the mountain ridge that leads towards Cat Rock. Here’s a link to All Trails: