The valley has been populated since ancient times, which was proved by different objects, considered being of Thracian origin. Some Bulgarian Christian tombs dating back to 12th-14th century were found on the neighbouring land of the town. In 1726 the newcomers bought the land and became owners of the valley and the surrounding hills. So the settlement of Chepelare was found. In 1836 the Chepelare inhabitants built the church of St. Atanasii and 3 stone turrets within 40 days. In 1876 a second temple Holy Mother of God was inaugurated. With the beginning of the 20th century and especially during the 30's and the 40's, the town was turned into a resort site.
The churches St. Atanas and Holy Mother of God, the Museum of Speleology and Bulgarian Karst, which is an unique museum not only for Bulgaria, but also for the Balkan Peninsula and Europe, the Museum of Ski Sport are the most visited attractions in the town.
The only transport available to Chepelare is by bus. There are regular bus lines to Plovdiv, Assenovgrad, Sofia, Smolyan, Pamporovo Resort, Devin, Shiroka Laka and other smaller villages.
1.5 km south from the town, near the road to Smolyan and Pamporovo, the bottom station of the two-chair rope lift is situated. It is 2471 m long, its transportation capacity is 600 persons per hour and it takes the skiers and tourist within 17 minutes to the Chala Peak (1873 m), where the starting points of the ski runs are located. 10 km south-west of the town is one of the largest and most famous winter resorts in the country – Pamporovo. At a road distance of 15 km southeast of the town, high on the top of Mechi Chal Peak the Rozhen Observatory is located, which is opened for tourists. There is no regular transport to this place, but one can climb up from Chepelare to the observatory within about two and a half hours.