The trail begins at the end of the asphalt road in the upper part of Lyutibrod village. Climbing gently southwest across a rocky meadow, you reach a ridge overlooking the Iskar River and the railway line. Turning south along the cliffs, the path leads to Prosechen Kamak—a 3-meter-wide passage cut into the rock.
Just under 1 km from the start lies Shishmanovo Kale. A path to the right leads up to the fortress ruins, offering magnificent river views and a small walkthrough cave.
At the saddle below the fortress, the loop route begins. Take the upper (left) path through the forest. In 10 minutes, a short detour leads to a scenic picnic spot over the Iskar meander and Zagrad area. Reaching the highest point (2 km mark), the old quarry path to Cherepish Monastery branches off to the left.
Descend right down the rocky slope. At the next fork, turn right to gently descend through the forest, reaching Mechata Dupka cave in under 10 minutes.
Continue down to the valley floor and around the rock base (the lowest point, below 300m elevation). A scenic lookout provides views of Zagrad, Shishmanovo Kale, and the Cherepish Rocks. From here, a 15-minute gentle climb returns you to the fortress fork, where the familiar path leads back to the start.