Start your tour by visiting the monument of a rebel and military commander, Vulchan. Vulchan Voivod is one of the most legendary names in history and his personality is the object of many beliefs and traditions wandering around the Bulgarian lands, and his exact fate is shrouded in mystery.

Next, head to a square where most festivals and concerts take place, and in the middle, there is the Freedom Monument, which symbolizes the involvement of the town of Elena in the fight against Turkish slavery.

From there, visit the Kaleto Park and climb a stone fortress to enjoy a beautiful panoramic view of the city.

From there, walk to the Assumption of the Virgin Mary Church, which was erected on the foundation of an old chapel with the help of Hajji Yurdan Beard, a local revivalist. Also, learn about the Razuhanov Houses, 5 charming houses build under one roof at the end of the 18th century by Hadji Dimitar Razsukanov for his sons.

Head to the Pop Nicolas House, which houses the Museum of Paleontology. The study, based at Sofia University - also called Kliment Ohridski, contains some of the fossils and minerals discovered by the students of the university during their study practice in the town of Elena, as well as other interesting exhibits. Bare in mind, the museum is closed on Mondays and Tuesdays. Admission is not included.

Take a walk through the narrow streets to visit the architectural and historical complex, Daskalolivnitsata (Teacher’s school). This is the first Bulgarian pedagogical school and was named by a teacher Petko Slaveikov. In the same complex of Daskalolivntsa, Kambur Inn is located. It bears the name of its owner, Stoyan Kambura, who was a part of the Elena Revolutionary Committee. It is a curious fact that initially this inn was located in the village of Yovkovtsi, but when the Yovkovtsi dam was built, the building was dismantled and moved to the yard of Daskalolivnitsa. There is currently an ethnographic exposition in the inn. In the complex you can also visit the temple St. Nikola, which hosts the exhibition“ Renaissance Art at the Beginning of the 19th Century - Mural, Icon, and Carving ”. This is the oldest temple in the Elena Balkan. It was built during the formation of Elena as a settlement. The first written document about it dates back to 1518. Legends say that many ancient manuscripts written on parchment were stored there. Here is the Temple of the Assumption of the Blessed Virgin which is still in effect. It was originally a wooden chapel, but after a while, it became too small for the residents of Elena and they decided to rebuild it by destroying the old fortress (kale) and using its stones. This was also done to prevent the Turkish garrison from being housed in the fortress. Admission is not included.

After strolling through Daskalolivnitsa, make your way to the Clock Tower. Its location was chosen so that its sound could be heard from anywhere in the city. It is one of the first clock towers in the country.

In the center of the town of Elena, hidden behind thick stone walls, the Hilarion Makariopolski Museum stands, unique in its presence, a focus on spirituality, a beloved and significant place for every Bulgarian. Тhe house was built in 1710 and is the oldest preserved building in the city, unique for its architectural solutions. In it were born the fighter for clerical independence Hilarion Makariopolski, his brother Nikola Mikhailovsky - a prominent literary and enlightened national revivalist and his son, the poet - satirist and fiction writer Stoyan Mihaylovski.

Head towards a local winery to taste 3 or 5 different wines - a white, a rose and a red - accompanied by the famous Elena delicacies. At the chateau, talk with a winemaker or the owners of the winery and discuss the history of the winery, the past and the legend about Kera Tamara and Ivan Alexander, a Bulgarian nobility of the Second Bulgarian Kingdom.