The narrow gorge of the Chepelare river is the only mountain pass through the Rhodope mountains south. Here, at the entrance to the gorge, in the V–IV centuries BCЕ the city of Stenimachos was founded. To guard the mountain path, on the high cliff above the city, a fortress was built.
In the year 1230 Bulgarian tsar Ivan Asen II has rebuilt and expanded the old fortress turning it into one of the most important castles in Bulgaria. This is why seven centuries later Stenimachos was renamed to Asenovgrad — the city of Asen. The church of the Holy Mother of God (circa XI CE) and the ruins of the Asen’s castle are now the main tourist attraction of the city.
However, the Asen’s fortress is not the only thing to see in Asenovgrad. There are multiple trails leading high into the mountains. Kutra eco-trail is one the most picturesque and easily accessible of them. It winds up through the Red Wall nature reserve to the top of peak Kutra (508 meters above sea level) that dominates the city. While ascending there it is worth to take short detours to check a few of the 58 chapels Asenovgrad is famous for. Saint Demetrius chapel (418 meters above sea level) also serves as the great viewpoint from which you can see the central parts of Asenovgrad and in the distance — the hills of Plovdiv.