Siege of Sofia

The Ottoman advance was halted for a long time before the walls of the fortress Koznitsa near the village of Smilyan. This fortress, like others in the region, played a key role in delaying the Ottoman conquest and in defending the Bulgarian lands in the Rhodopes.

The stubborn resistance of these fortresses and their garrisons demonstrated how important this part of Bulgaria was for the defense against Ottoman expansion.

During the siege of Sredets, the Ottoman army undertook several advances into the Rhodopes, with one of the main columns led by Jedid Pasha. This column entered the valley of the Chaya River, also known as the Chepelarska River, aiming to break through the Bulgarian defense and secure a route into the interior of the country. Despite the advance, the Ottomans encountered serious resistance at the fortress of Zarenitsa, located southeast of Narechen. All attempts by Jedid Pasha and his troops to penetrate this strategic fortress proved unsuccessful, demonstrating the strength and determination of the Bulgarian defenders.

Nevertheless, one night the defenders of Zarenitsa decided to abandon the fortress, likely due to exhaustion of supplies or as a strategic withdrawal. The Ottomans pursued them but, in dense fog, fell into a nearby ravine where they perished. Their bodies remained unburied for a long time, and the area around the ravine came to be known as Lyuti Dol, which bears witness to the tragic events and heavy losses suffered by the Ottoman army in this region.

Simultaneously, another Ottoman column, led by Ibrahim Pasha, advanced along the course of the Vacha River with the goal of capturing the fortress of Beden, located near the village of Beden in the Devin region. This fortress was under the command of Goryo Voivoda, who organized fierce defense. According to local legends, all Ottoman assaults on Beden were repelled, and their attempts to breach the fortress remained unsuccessful. This attests to the high fighting spirit and skilled leadership of the Bulgarian defenders.

As supplies in Beden began to run out, the defenders decided to make a sally to avoid complete encirclement and death by starvation. Many shepherds and their flocks had taken shelter in the fortress, leaving their dogs to starve for several days. One night, the Bulgarians opened the fortress gates and left, while the starving dogs attacked the besieging Ottomans, causing chaos. Taking advantage of the disorder, the Bulgarians broke through and retreated toward Trigrad, where the struggle continued with even greater intensity.

The local population in Trigrad sought refuge in the surrounding deep caves, which the Ottomans dared not enter. They walled up the entrance to the Chelevecitsa cave, expecting those sheltering inside to surrender. However, the people in the cave preferred death to surrender; numerous human bones were later found in the cave, confirming this tradition and bearing witness to the tragic end of the defenders.

The conquest of the Rhodopes proved extremely difficult for the Ottomans and required great effort and sacrifice. It is believed that this process lasted from 1373 to 1375, with Bulgarian resistance in the fortresses of Zarenitsa, Zagrad, and Beden, as well as in the Trigrad area, significantly delaying the Ottoman advance and inflicting heavy losses on the conquerors. These events illustrate the strength of the Bulgarian defense and the determination of the local population to oppose Ottoman expansion in the Rhodopes.

Folk traditions in Bulgaria preserve the vivid memory of numerous heroic battles fought in the defense of fortresses located in the strategic valleys of the Struma and Mesta rivers. These fortresses were key to the defense of Bulgarian lands against the Ottoman invasion and stand as symbols of the unwavering will of the local population to preserve their freedom and independence.

In the valley of the Struma River, there were several important fortresses, among them the Kaleto fortress near the village of Gradevo in the Predela area and the fortress of Krupnik. These strongholds served as strongpoints for the Bulgarian defense and were the scenes of fierce battles. Particularly memorable is the defense of the Petrich fortress, which, according to a tradition published by B. Tsvetkov, was conducted with exceptional self-sacrifice and heroism.

At the head of the defenders of the Petrich fortress stood a beautiful maiden who became a symbol of the resistance. She waved a green banner before the eyes of the besiegers, this green banner being a symbol of the fortress’s independence and the spirit of its defenders. This brave act not only inspired the garrison but also provoked the anger of the Ottoman troops.

The son of the Ottoman commander, attracted by the maiden’s beauty and courage, sought to take her into his harem. He sent expensive gifts with a proposal: “Voivode, surrender the fortress, the sword, and yourself.” This proposal was an attempt to end the siege through negotiation and bribery, but the maiden categorically refused to accept the gifts or to betray the fortress and her people.

In response to her refusal, the besiegers set the fortress on fire, hoping that the defenders would leave with their leader to save their lives. Nevertheless, all the defenders perished in the flames, fighting to their last breath and refusing to surrender. This tragic yet heroic death left a deep mark in the popular memory.

After the fall of the fortress, the bey commanding the Ottoman troops ordered that the maiden be buried with honors. A red flower was planted on her grave by the bey’s order, which blooms every spring around the fortress. The local population calls this flower the “Maiden’s Flower” and regards it as a symbol of her courage and self-sacrifice.

According to another tradition, also published by B. Tsvetkov, the garrison of the fortress near the village of Gorno Spanchevo also heroically defended the stronghold. The surrounding population sought refuge there and joined in the defense. The numerous assaults of the besiegers were successfully repelled by the defenders, who showed exceptional endurance and fighting spirit.

To maintain the morale of the defenders, the population not directly involved in the fighting organized festivities with drums, bagpipes, and songs. These celebrations unsettled the Ottoman troops and sustained the spirit of the Bulgarian defenders, creating an atmosphere of hope and resistance despite the heavy siege.

However, the besiegers managed to discover and cut off the water supply to the fortress near Gorno Spanchevo, which was crucial for the survival of the garrison and the population. After running out of water, the defenders and the population were forced to leave the fortress through a secret exit to avoid destruction.

After their withdrawal, the defenders and the population hid in the mountains, from where they continued the fight against the Ottoman conquerors. This tactic of guerrilla resistance shows that even after the fall of the fortresses, the Bulgarian spirit was not broken and the struggle for freedom continued.

Folk traditions also preserve the memory of heroic battles in the defense of fortresses in the valley of the Mesta River. Among them are Momina Fortress near the present-day town of Gotse Delchev, Sitan Kale near Bansko, and two fortresses near Yakoruda. These strongholds were also important centers of resistance against the Ottoman invasion.

Despite the strong resistance, the powerful fortresses of Velbazhd (modern Kyustendil) and Melnik were captured only in 1387, which shows how long and stubborn the Bulgarian defense in this region lasted. These events and the traditions about them remain an important part of Bulgarian historical memory and national identity.

The fortress Momina Kula rises majestically near the village of Bukovo, situated on a strategic height above the Mesta River. This position provides it not only with excellent visibility but also with natural protection, making it an important military point in the region. Around it, numerous legends have developed, collected and published by the researcher B. Tsvetkov, each adding a different nuance to the history and significance of the fortress.

The first legend links the construction of Momina Kula to the royal family, claiming that the fortress was built by Mara, the sister of Tsar Ivan Shishman. According to this version, Mara managed to escape captivity before the construction began, suggesting that the fortress was conceived as a symbol of resistance and a refuge against the Ottoman invaders.

The second legend, considered more credible, portrays Mara as a brave and determined maiden who took command of the fortress’s defense. She became a symbol of heroism and steadfastness, leading the defense against the attackers. However, when the defense became impossible and the fortress was threatened with capture, Mara chose to throw herself into the waters of the Mesta River rather than fall alive into the hands of the conquerors. This act of self-sacrifice left a deep mark in the popular memory, and the fortress was named Momina Kula in her honor. Moreover, the gorge of the Mesta River where the fortress is located was named Momina Klisura, further cementing the connection between the place and the legendary figure of Mara.

The third legend is a continuation of the second and does not contradict it but rather complements the story by recounting events that took place in the 17th century. During this period, when Bulgarians were subjected to forced Islamization, the daughter of the Bulgarian voivode Breza became the leader of a hajduk band. She settled in the fortress Momina Kula and for a long time successfully repelled attacks by Ottoman troops. Under her leadership, the fortress became a center of resistance, and she ruled over the entire surrounding area, avenging the conquerors and inspiring the local population not to surrender.

Besides Momina Kula, other fortresses in the region played key roles in resisting the Ottoman invaders. According to one folk legend, the garrison of the fortress Kalyata near Razlog was commanded by the boyar Dragostin. This garrison offered stubborn resistance to the conquerors, who quickly realized they could not break the fortress defenders by force. In response, the Ottoman troops adopted a tactic of cutting off the garrison’s access to the river at the foot of Kalyata, attempting to exhaust the defenders by depriving them of water and provisions.

Folk legends also testify to the resistance of fortresses in the Sub-Balkan valley, which also opposed the Ottoman invaders. Among them are Tvarditsa, Mugluk, the small fortresses near the villages of Tazha and Tsurkvitsa, which are connected with Zlatitsa, as well as Zlatitsa itself. These fortresses, located at strategically important points, served as strongholds for the Bulgarian resistance and symbolized the unyielding spirit of the people in the struggle against the conquerors.

Momchil Voivode, originally from the village of Lădzeene, today known as the village of Anton, distinguished himself as one of the most successful Bulgarian military commanders in the struggle against the Ottoman invasion. With his detachment, he dealt a heavy defeat to the Ottomans in the locality of Topkoria, where a decisive battle took place. In this clash, the Ottoman leader Orhan was killed, whose death left a deep mark in the local memory. At the place of his death, the Ottomans dug a well, which became known as Papabunar, and Orhan himself was buried in a sack, with a pile of stones left on his grave as a symbol of lasting respect and remembrance.

In the same battle at Topkoria, another Ottoman commander, Kasik Baba, also perished, which further weakened the Ottoman forces. On the Bulgarian side, the losses were also significant – among the fallen was Momchil Voivode’s stratēnik (military officer), Todor. In memory of his self-sacrifice, the meadows southwest of the Papabunar well were named Todorichane, thus the local population immortalized his name and heroism in the fight against the invaders.

At the same time, the defenders of the fortresses in the Srednogorie region, located near the villages of Glufishevo, Turiya, Zlatosel, Ovchepoltsi, Srebrino, Vetren, and others, did not spare their blood in attempts to stop the Ottoman advance. These fortresses formed a fortified complex consisting of three key fortresses – the Great Kale, the Small Kale, and Kurvingrad, situated west of Mount Beter, in the area of today’s village of Nova Mahala. This fortified complex had strategic importance as it controlled the important Kaloyanov Road, along which the Ottomans tried to penetrate into the heart of the Bulgarian lands.

The conquerors advanced from the plains toward the fortified complex but encountered fierce resistance. Hrishten Voivode, another prominent Bulgarian military commander, positioned his fighters in the area of the Medven mound, aiming to block the road to the nearby pass and to delay or stop the Ottoman advance. To ensure better visibility and control over the battlefield, he sent his two sisters, Stana and Milka, to a steep cliff from where they could observe the development of the battle.

Hrishten Voivode warned his sisters to remain calm as long as the flag was flying on the mound, which was a symbol of Bulgarian resistance and hope. He told them that if the flag fell, it would mean that the battle was lost, and then they should seek refuge in the mountains to avoid falling into the hands of the enemy. This tactic demonstrates not only the military wisdom of Hrishten Voivode but also his care for his loved ones and for the survival of the Bulgarian forces in the difficult moments of the battle.

During the siege of Sredets, the fighters under the command of voivode Hrishten fought with exceptional bravery and determination. Nevertheless, the Ottoman forces were numerous and ultimately managed to prevail over the city's defenders. In the evening, when the battle reached its critical moment, the banner of the Bulgarians fell, symbolizing the loss of the fortress and the defeat of the defenders. In this dire moment, voivode Hrishten himself perished, his death deeply shaking the spirit of the remaining fighters and the inhabitants of the camp.

After the death of the voivode and the fall of the banner, cowardice and despair spread throughout the camp. The situation became so dire that the defenders themselves began to urge their sister to surrender to the Ottomans, seeking an end to the suffering and hopeless struggle. At this moment, the voivode’s sister, Milka, showed exceptional courage and cunning. She pretended to agree to the surrender in order to buy time and carry out her plan.

Milka suggested to her sister that they fix their hair so they would not go before the victors with disheveled and dirty hair, which was a symbol of shame and defeat. While combing her sister’s hair, Milka subtly braided her braid together with her own, creating an inseparable bond between the two. Then, in an act of heroic sacrifice, she threw herself off the cliff into the abyss, pulling her sister down with her. This tragic incident left a deep mark in local memory, with the cliff from which the two sisters leapt being named Milka’s Rock in their honor.

In memory of voivode Hrishten, the neighboring village was named after him, and this name has been preserved to this day as a living reminder of his bravery and self-sacrifice.

According to another tradition, published by P. Deliradev, the fortress of Dushkovcheni, located in the valley of the Dushkovcheni River, north of the present-day village of Byata, also fell under Ottoman pressure. After the loss of the fortress, the daughter of the local ruler, Yana, gathered a band and continued the fight against the Ottomans in this region for many years. Yana died the death of the brave, but her glory outlived time. During her lifetime, she was called Mad Yana, and the river along which her band operated was named Mad Yana and still bears this name today.

A local tradition also tells of a great battle in the area of Kasapka near the village of Zmeyovo, where Ottoman troops led by Zinan Pasha clashed with Bulgarian warriors under the leadership of voivodes Blagoy and Radoy. Despite their brave resistance, the Bulgarians were repelled and retreated toward the Kazanlak field. From there, they continued their withdrawal toward the Balkan range, where the struggle against the Ottomans continued with unrelenting persistence.

In 1380, the Ottoman forces undertook the siege of the important Bulgarian fortress of Sofia, then known as Sredets. The commander of the Ottoman army was Lala Shahin, who held the high rank of Rumelian Beylerbey and personally led the troops in battle. The Ottomans aimed to capture Sofia, which occupied a strategic location and controlled the extensive Sofia field – a flat, rich, and fertile plain of great significance to the region. Despite numerous attempts, the Ottomans failed to take the fortress that year.

The defense of Sofia was entrusted to the Bulgarian military leader Ban Yanuka, who organized the defense with determination and skill. Under his leadership, the defenders successfully repelled all enemy assaults and storming attempts. The fortress was strong and very well fortified, making every Ottoman attack fruitless. Despite repeated raids and storming efforts, the Ottoman forces could not breach the defenses or capture the city. These unsuccessful attacks proved not only futile but also harmful to the Ottoman army, as they suffered heavy losses.

Lala Shahin, who personally commanded the attacks, sent a report to the sultan in which he presented himself as the serdar of the victorious Ottoman forces. Nevertheless, he acknowledged that the fortress of Sofia could not be taken soon by force and bravery alone. He noted that the successful capture of the city required cunning military plans and skillful tactics, as direct assault proved ineffective. The Ottoman soldiers participating in the siege suffered great casualties, described as self-sacrifice akin to kurban – a sacrificial offering in the name of war and conquest.

At that time, the Ottoman forces were also fighting the kuffar armies in Central Rumelia, which further complicated the military situation and the distribution of forces. Lala Shahin made several attempts to capture both the Sofia field and the fortress itself, but without success. After repeated failed attacks, he became convinced that victory could not be achieved by brute force alone and that the siege had to continue by other means.

The siege of Sofia did not end in 1380 but continued in the following years, with the Ottomans persisting in their attempts to seize the city in 1382. According to legendary accounts, during this period Tsar Ivan Shishman actively fought against the Turks in the Sofia region to aid in the city's defense. His name is associated with fortifications such as Shishman’s Kale near Samokov and the fortress of Urvich in the Iskar River gorge, which were important for the region’s defense. It is believed that the sons of Tsar Ivan Alexander – Asen and Michael – died in battles near the Kokalyanski Urvich fortress, underscoring the severity and ferocity of the military actions in this area during the Ottoman expansion.

There is a widespread tradition according to which the fortress of Sofia, known in the Middle Ages as Sredets, was captured only after the Bulgarian military commander Ban Yanuka was taken prisoner during a hunt, using cunning. This narrative tells of a dramatic turn in the city's defense, in which the figure of Ban Yanuka played a key role. However, archaeological excavations conducted in recent years contradict this tradition by providing concrete evidence of how the breach in Sofia's fortress wall was actually made.

At the western gate of the Sofia fortress, archaeologists have discovered an opening in the wall that is not natural but artificially created. This opening was made with the help of battering machines, which testifies to an organized and well-prepared Ottoman siege employing heavy artillery to break through the defensive structures. Near this opening, a lime kiln was found, which had been built by the fortress defenders in order to close and reinforce the breach in the wall. This shows that the Bulgarian defenders made persistent efforts to hold the fortress and prevent the penetration of Ottoman troops.

The resistance of Sofia's defenders was long and stubborn, which delayed the city's capture. Nevertheless, the fortress fell only in 1382, which speaks to the considerable endurance and determination of the Bulgarian defenders in the face of Ottoman aggression.

Meanwhile, in 1388, an Ottoman army of about 30,000 men, led by Ali Pasha, crossed the Eastern Balkan range through the Aytos Pass. This strategic pass was key for the entry of Ottoman forces into Moesia. There are traditions of heroic resistance by the defenders of the fortress near the present-day village of Rytlina, located in the area of the Aytos Pass, which testify to fierce battles and determined defense of the pass.

Upon entering Moesia, the Ottoman army captured the fortress of Ovchaga, located near the present-day village of Asparuhovo. This fortress had strategic importance as it closed the northern exit of the Aytos Pass, which allowed the Ottoman troops to control movement in the area and secure a safe route for their further advance.

After capturing Ovchaga, the Ottoman forces continued their advance and seized a number of settlements in northeastern Bulgaria, among which were Shumen, Madara, Venchan, Ovech (today's Provadia), Vicha — Viechene (the present Cape St. Athanasius), and others. From these conquests, the Ottoman forces directed themselves toward Varna, which was an important strategic and economic center of the region.

Medieval Ottoman historians present the actions during this campaign as a series of victorious and rapid conquests, emphasizing that the Ottoman army did not encounter serious resistance. This official narrative aims to highlight the military power and indisputable victory of the Ottomans.

Some modern researchers share this viewpoint, describing the campaign as easy and successful, without significant obstacles. However, the reality was more complex. The Bulgarian population in the attacked areas offered resistance in many places, although it was surprised and insufficiently organized due to the feudal fragmentation of the country. This internal division complicated the coordination of defense but did not prevent the Bulgarians from refusing to surrender to the conquerors and from fighting for their freedom and territory.

Thus, although Ottoman chronicles paint a picture of rapid and trouble-free conquests, historical and archaeological data show that the siege of Sofia and the subsequent Ottoman advances in northeastern Bulgaria were accompanied by stubborn resistance and significant efforts on the part of the Bulgarian defenders and population. This underscores the complexity of the process of Ottoman conquest and the heroism of the Bulgarians during this difficult period.

The devastation of the surroundings of Tutrakan exerted strong pressure on the inhabitants, who were ultimately forced to seek a truce and once again hand over the keys to the fortress gates to the Ottomans. This move demonstrates how severe the conditions for defense had become and how the Ottoman tactics of attrition and threats of destruction were effective in breaking the resistance of the towns.

Meanwhile, the fortress of Silistra, which according to the chronicler Leunclavius surpassed all other towns and fortresses of Tsar Ivan Shishman in size, the splendor of its buildings, the wealth of its inhabitants, and fortress defense, fell into the hands of the Ottomans after stubborn resistance. This loss was a significant blow to the Bulgarian defense, as Silistra was one of the most important and well-fortified towns in the region, underscoring the seriousness of the Ottoman advance and the difficulties faced by the Bulgarian defenders.

In 1388, the Ottoman forces undertook strategic actions aimed at wedging themselves between the Despotate of Dobruja and the Tsardom of Tarnovo, which was part of their broader campaign to expand influence in the Bulgarian lands. This plan was of key importance, as the Ottomans sought to weaken the ties and alliances between the Bulgarian domains to facilitate their further advance.

The chronicler Saadeddin provides an account of the siege of Nikopol, which, however, proves to be misleading and implausible, having led to erroneous conclusions among many researchers. According to him, Ali Pasha, one of the Ottoman commanders, besieged the fortress of Nikopol, where Tsar Ivan Shishman was located. Despite his efforts, Ali Pasha failed to capture the city and therefore sought assistance from Sultan Murad.

Sultan Murad appeared before Nikopol with the "largest army," according to Saadeddin, which should emphasize the significance of the operation and the Ottomans' determination to conquer the fortress. At this moment, Ivan Shishman entered into negotiations with the sultan, with Murad agreeing to leave Nikopol to the Bulgarian tsar in exchange for the surrender of Silistra—a strategically important city on the Danube.

Despite the agreement reached, Ivan Shishman did not fulfill his promise and began to fortify Silistra, which was a direct violation of the arrangements and provoked a new Ottoman reaction. As a result, Murad undertook a renewed siege of Nikopol, which this time forced Ivan Shishman to comply with the Ottoman demand and surrender Silistra. This move allowed the Bulgarian tsar to retain his throne, albeit at the cost of losing an important city.

However, Saadeddin's account contains several questionable elements. He claims that the troops of Ali Pasha and the sultan's army had to besiege Nikopol three times to intimidate Ivan Shishman, and the purpose of these sieges was to force him to surrender Silistra. Nevertheless, the Ottoman forces at that time were sufficient to capture Silistra without needing the Bulgarian tsar's consent, which calls into question the truthfulness of the described negotiations and sieges.

Moreover, Saadeddin does not mention the conquest of other Bulgarian fortresses on the way to Nikopol, which is inexplicable, since the capture of such fortresses would have been inevitable and necessary to secure the rear of the Ottoman troops. This omission further undermines the credibility of his narrative.

According to the chronicler, Ivan Shishman was sometimes in Nikopol, sometimes in Silistra, while simultaneously fortifying Silistra, which shows that the Bulgarian tsar was trying to maintain control over key positions in the region. Nevertheless, Sultan Murad showed unusual leniency towards Ivan Shishman by not directing all his forces against Tarnovo, which can be explained by political or military considerations.

Furthermore, after the defeat at Plocnik in 1387, Sultan Murad was unlikely to have been able to lead the "largest army" and decide the fate of a Bulgarian fortress, as Saadeddin claims. This suggests that the events described by the chronicler are highly exaggerated or distorted, necessitating a more careful and critical reading of the sources concerning the siege of Nikopol and the related events in 1388.

According to the Ottoman chronicler Mehmed Neşri, in 1388 the Ottoman forces under the command of Ali Pasha undertook a large-scale campaign that led to the capture of several important Bulgarian fortresses. Among them were Ruse, Cherven, Novgrad, and Svishtov – strategic sites that played a key role in the defense and control of the territories around the Danube River and the interior of the Second Bulgarian Empire.

The fortress of Ruse, one of the first to be taken, is situated on a height with steep slopes descending towards the Danube River and the Rusenski Lom River. It was built on the site of the ancient Roman castellum Sexaginta Prista, which testifies to its long history and strategic importance dating back to antiquity. Although today no above-ground remains of the Ruse fortress survive, archaeological excavations and finds provide valuable information about its structure and significance. A military club has been erected on the site of the fortress, and during its construction walls with reused ancient stone inscriptions were discovered, as noted by the renowned Bulgarian archaeologist the Škorpil brothers.

In 1903, foundations of a fortress were uncovered in the garden of the military club in Ruse, and in 1911 walls were found to the west of the club, confirming the presence of a significant medieval fortification. The Ruse fortress, together with the fortress of Giurgiu located on the northern bank of the Danube, formed a twin-fortress system. This pair of fortifications was of exceptional importance for protecting a convenient crossing over the river. The fortress of Giurgiu was part of the Tarnovo Tsardom until its fall under Ottoman rule, highlighting the strategic importance of this area for the Bulgarian state.

Another key site captured in the same year was the fortress of Cherven, which existed since Roman times but whose role and significance increased especially during the Second Bulgarian Empire. It rises on a high hill surrounded on three sides – north, west, and south – by the Cherni Lom River, making it naturally protected. The northern and southern slopes of the hill are almost vertical towards the river, rendering access to the fortress from these directions practically impossible.

The fortress of Cherven is enclosed on all sides by a massive fortress wall built of rubble stones bonded with mortar, with a thickness reaching up to two meters. It has two gates – eastern and western – with the western gate further protected by a well-preserved tower. This tower has a rectangular shape with internal dimensions of 8.60 by 5.50 meters and external dimensions of 10.30 by 8 meters. It is constructed of rubble stones bonded with mortar and consists of four floors. The first two floors are 1.65 meters high, and the following two are 2.80 meters high, indicating a complex and well-thought-out defensive structure designed to provide maximum protection to the western gate and to hinder attackers.

The conquest of these fortresses in 1388 by the Ottoman forces under Ali Pasha represents an important stage in the Ottoman expansion into the Balkans. Control over Ruse and Cherven gave the Ottomans strategic positions for controlling the Danube River and the adjacent territories, allowing them to strengthen their presence and continue pressure on Bulgarian lands. These events marked a significant shift in the balance of power in the region and prepared the ground for the further Ottoman conquest of Bulgarian territories.