Livonia in the 14th Century

The historical territory of Livonia covered approximately the modern-day areas of Latvia and Estonia, with some border adjustments in the southwest and east of Latvia, and in the northeast of Estonia. Livonia was composed of a number of feudal political entities: the Archbishopric of Riga, the Bishopric of Courland, the City of Riga, the Bishopric of Tartu, and the Bishopric of Ösel–Wiek. In addition, there was the Livonian Order’s State, which held lands across both Latvian and Estonian ethnic territories, connected by a territorial corridor along the Gauja River.

Of special note are the regions of Harjumaa and Virumaa (known historically as Harija and Virija), which remained under the control of the Danish Crown until the year 1347.

This overview focuses specifically on the 14th-century political structures and sources of power that existed within the Latvian part of Livonia, as well as the key historical events that shaped Livonia during the 14th century.

The Archbishopric of Riga

Since 1225, Livonia was a march (border province) of the Holy Roman Empire of the German Nation, and the Archbishop of Riga was nominally considered an imperial prince. By around 1290, the archbishopric covered approximately 18,000 km² in the regions of present-day Latgale and Vidzeme. The Gauja corridor divided the territory into two cultural zones—Livonian and Lettish. The Archbishop was elected by the Riga Cathedral Chapter, but formally appointed and confirmed by the Pope in Rome.

The bishopric was divided into around 23 territorial units, or parishes, which were potentially aligned with castle districts or regional divisions. In the east, the territory bordered the Principality of Pskov, and this boundary became the site of continuous frontier warfare throughout the 14th and 15th centuries.

Nominally, the Archbishop of Riga also held spiritual authority over the territories of the Livonian Order in Vidzeme, Latgale, and Zemgale, since the Order did not have its own bishops. The Archbishop was also the Bishop of the City of Riga. These Order-controlled regions, together with the archbishopric, formed the Archdeaconry of Riga, a central administrative unit.

At the same time, the Archbishop of Riga held the title of Metropolitan (chief bishop) over the bishops of Tartu (Dorpat), Ösel–Wiek (Saare-Lääne), Courland (Kursa), Samland, Pomesania, Ermland, and Culm (Kulm). These seven dioceses, together with the Archdeaconry of Riga, formed the Ecclesiastical Province of Riga.

Up until the early 16th century, the archbishops referred to themselves as:

“By the grace of God and the apostolic see, Archbishop of the Holy Metropolitan Church of Riga, Metropolitan of the lands of Prussia, Courland, the Livs, the Letts, and the Estonians, and Prince of the Holy Roman Empire.”

Due to the continuous terror and military pressure from the Livonian Order in the second half of the 13th and early 14th centuries, several archbishops were forced to flee to Rome, living in the papal court, or in better cases, managed to be transferred to other dioceses. The Order fought to install its own candidates into the archiepiscopal seat, which led to frequent open conflicts between the Cathedral Chapter and the City of Riga on one side and the Livonian Order on the other.

By the early 15th century, the archbishops had granted lands within the archbishopric to over 2,000 secular vassals. The 14th century is considered a period of consolidation of vassal power. Prominent vassal families such as the Tiesenhausens, Rozens, and Ungerns built several castles in Liv and Lett regions during this time. Their wealth is demonstrated by an event in 1361, when Archbishop Fromhold pledged the regions of Dzērbene and Piebalga to his vassal Bartholomew Tiesenhausen, receiving 2,800 silver marks of Riga (1 mark = 206 grams), equivalent to 576 kg of silver.

The Archbishop himself owned 22 castles, the most important being located in Koknese, Limbaži, and Rauna—residences he alternated between. Within the archbishopric territory, apart from Riga, there were three cities: Koknese, Limbaži, and Straupe.

Koknese and Limbaži had autonomous administrations led by burgomasters and councillors, with the burgomasters serving as vassals of the archbishop. Straupe, however, had a different legal situation—it had developed on the fief lands of the Rozen family, who were vassals of the archbishopric. The City of Riga granted Straupe city rights in the mid-14th century.

The Riga Cathedral Chapter

The Riga Cathedral Chapter was the archbishop’s council in secular and spiritual matters—a clerical college also responsible for the secular governance of the Archbishopric. The chapter consisted of 12 canons (referred to in German as Domherren), who, together with the archbishop as the 13th member, symbolically represented Jesus and his twelve disciples.

Between 1210 and 1373, the Riga Cathedral Chapter operated under the rules of the Premonstratensian Order, wearing white robes and living communally according to monastic traditions and the Rule of St. Augustine. The canons’ permanent residence was a cloister built along the southern wall of the Riga Cathedral, which also housed the Riga Cathedral School—today the building of the Latvian Museum of Maritime and History, with its preserved Gothic cloister.

On October 10, 1373, Pope Gregory XI granted the canons permission to adopt the Augustinian rule formally, after which their white garments were replaced with black. This change in rule prompted the Livonian Order to seek papal approval for the chapter to adopt the statutes of the Teutonic Order, effectively turning the canons into knights of the order and allowing the Order to appoint chapter members.

During the resulting conflict, Archbishop John IV, together with the chapter, was forced into exile in Lübeck in 1391. On March 10, 1394, following a directive by Pope Boniface IX, the Riga canons were compelled to wear the habit of the Teutonic Order and adhere to its statutes. This arrangement persisted throughout the 15th century.

In the 14th century, the Riga Cathedral Chapter held estates including the parish district of Ķizbele with Krimulda Castle, Dole Castle on Dole Island, territories on the left bank of the Daugava between Dole Island and Riga’s patrimonial lands, several houses within Riga, rural estates around Riga, and in northern Courland, the Dundaga Castle and the Tārgale district, which included 30 villages and several manors. These lands had entered the chapter’s possession primarily through donations.

The Bishopric of Courland

Of the three ecclesiastical principalities in medieval Latvia, the Bishopric of Courland was the smallest, covering an area of approximately 4,500 km². It was divided into three separate parts—north, west, and south—by territorial corridors controlled by the Livonian Order. The bishop’s residence was located in Piltene.

Since 1290, the bishops of Courland, along with the six-member cathedral chapter, were chosen exclusively from among the priests of the Teutonic Order, effectively making the bishopric, by the 14th century, a de facto extension of the Livonian Order. The Bishop of Courland also held ownership of Ruhnu Island (Roņu sala).

Although the bishop and the chapter members were appointed from the ranks of the Order’s brethren, relations between the bishopric and the Order were often strained. For example, in 1300, Bishop Burchard complained to the Livonian Master that, under the orders of the Komtur of Kuldīga and the instigation of a man named Wigand, military forces from the Valtaiķi castle district raided and looted the bishop’s village of Bērbone.

The same Wigand was also accused of stealing a small barrel of wine intended for the Holy Communion, drinking it, and ordering his servants to trample the communion wafers and chalice underfoot. Furthermore, he gave the altar cloth used for the Eucharist to his maid, who then made it into a headscarf.

Between December 3, 1309, and Bishop Burchard’s death in 1321, the Bishopric of Courland was directly administered by the Livonian Order, based on an agreement in which the bishop surrendered control of the bishopric in exchange for an annual pension of 25 Riga marks, one village, and spiritual jurisdiction throughout Courland.

The State of the Livonian Order

The Livonian branch of the Teutonic OrderFratres beatae Mariae virginis ordinis domus Teutonicorum in Livonia or Dutscher orden to Lifflande—was established in 1237, following the defeat and merger of the Sword Brethren. The Order gained its lands through conquest and governed them based on the right of occupation (ius occupanti).

The territory of the Livonian Order’s State included all of modern Zemgale, southeastern Latgale, a strip of land in Vidzeme east of the Gauja (from the outskirts of Riga), most of Estonia, and around two-thirds of Courland (Kurzeme)—amounting to a total area of about 67,000 km². In 1305, the Order acquired Daugavgrīva Abbey and surrounding areas from the Cistercians, gaining control over lands between the Lielupe River and the Baltic Sea, extending as far as the Gauja, as well as Cistercian properties in Riga and its rural districts. Two documents dated 10–11 October 1385 record the supposed transfer of the Principality of Polotsk under the protection of the Order, though this claim was never effectively recognized or enforced.

The residence of the Livonian Master, the elected head of the Order in Livonia, was located in Cēsis until 1330, and from 1330 to 1429 in Riga. Nominally, the Livonian branch inherited a vassal relationship with the Archbishop of Riga from its Sword Brethren predecessors. However, from the mid-13th century onward, the Order strove to free itself from episcopal jurisdiction. After a long period of conflict and investigation, the matter was settled on 7 May 1366 by Grand Master Winrich von Kniprode, who ordered Archbishop Fromhold of Fifhüsen to relinquish any claims to allegiance from the Livonian Master. (At the same time, the Grand Master forced the Livonian Order to give up claims of sovereignty over the city of Riga.) In practice, the Order made no attempt to recognize the Archbishop as its feudal overlord.

The Order’s administration was corporately governed by elected officials known collectively as Commanders (praeceptores, Gebitiger).

The head of the Livonian branch was the Master (Magister, Meister, Obirster Gebitiger), appointed and dismissed by the Grand Master of the Teutonic Order with the consent of the General Chapter. Upon confirmation, the Livonian Master became one of the most senior leaders in the Teutonic Order and formally represented the Grand Master in Livonia. In the internal hierarchy, he ranked directly below the Master of the German Province and was required to participate in the election of the Grand Master and General Chapters. The Master’s seal was pressed in red wax.

The next highest official was the Land Marshal (marsalcus terrae, Landmarschalk), the Master’s deputy, military commander in his absence, and acting leader during interregnums. Elected by the Chapter, his residence was in Sigulda (Segewald), and his seal was pressed in green wax.

Commanders (Komturs) were in charge of the Order’s most important castles and their territories, known as Komtureien. Their titles included the name of the castle they managed. The Livonian Chapter elected and transferred them between posts. Each commandery had its own banner, but only a few descriptions of these flags survive, making it unclear whether each commandery had a unique flag or only some did.

Komturs were responsible for supplying their garrison, maintaining and repairing fortifications, and governing local peasants. They had their own seals (yellow wax). Literacy was not a requirement—by 1459, the Komtur of Elbing admitted he could neither read German nor Latin and jokingly remarked that neither could his scribe, “because he wasn’t a doctor.”

Vogts, like komturs, were commanders of castles and territories. Initially, their role was secondary, often governing less significant or border fortresses, but over time, especially in buffer zones, their importance grew. Vogtships were located in Cēsis, Kandava, Rēzekne, Sēlpils, Grobiņa, and Bauska. As pressure from neighboring powers increased, these areas—especially Bauska and Grobiņa (facing Lithuania) and Rēzekne (facing Polotsk)—gained strategic importance.

The Compann (Companion) was the deputy of a komtur or vogt, a role that emerged due to a shortage of eligible officials. Companns led troops in battle and managed castle operations.

The Livonian Master was required to convene an annual assembly (Capitulum, Gebetiger Capitell) of the Order’s commanders and officials to report on administration, elect new masters, appoint or transfer officials, and resolve disputes. In the event of the Master’s death, a new chapter was summoned by the Land Marshal. Chapters were typically held in Cēsis or Riga.

The majority of the Order’s brethren were foreign-born—mainly from Westphalia and the Rhineland. According to 15th-century visitation records, only two knights were born in Livonia; the rest included 161 from Westphalia, 26 from the Rhineland, and 4 from Meissen. Local recruitment was negligible. In 1421, Siegfried Lander of Spanheim pleaded with the Grand Master to send new knights to Livonia urgently, as a Lithuanian invasion was expected.

The Order employed a significant number of servants and officials known as the Blackheads. From the 14th century, they were organized into the Brotherhood of the Blackheads, under the patronage of Saint Maurice. They were based in several castles—Riga, Sigulda, Cēsis, Kuldīga, and Grobiņa. Statutes from Kuldīga and Grobiņa list roles such as: cupbearer, scribe, kitchen overseer, steward, tailor, castle smith, storekeeper, and female workers (mejerschen)—the latter possibly also serving as companions. The Blackheads were relatively wealthy, often lending money to Order vassals and maintaining close ties with the Blackheads of Riga. Drinking was a celebrated activity among them and explicitly addressed in the brotherhood’s statutes.

As in the Archbishopric of Riga, the Livonian Order’s State included urban centers. In present-day Latvia, these were: Cēsis, Kuldīga, Valmiera, Ventspils, and Aizpute.

  • Cēsis received city rights in 1224,

  • Valmiera in 1323,

  • Kuldīga in 1355, and

  • Ventspils in 1378.

In the 14th century, Cēsis and Kuldīga were fortified cities with independent governance, strong economies, and strategic importance. Ventspils received its walls in the late 14th to early 15th century—so prominent that mocking them was prohibited by law, with violators facing a fine of three marks of gold.

All these cities developed around Order castles, with dwellings gradually expanding into suburbs and eventually being encircled by defensive walls. Their inhabitants included merchants supplying local peasants with goods (mainly salt), collecting agricultural produce, and engaging in transit trade. This is evidenced by the membership of Cēsis, Valmiera, Kuldīga, and Ventspils in the Hanseatic League.

The City of Riga

By the 14th century, thanks to its wealth, power, and military strength, the City of Riga had risen to become the fourth major landholder (de facto sovereign) in what is now Latvia, and the only secular city-state in the region.

The city was governed by the Riga City Council (Rāte), which consisted of 20 councillors, including 4 burgomasters and 2 treasurers. The city maintained its own chancellery with a city secretary and an independent court, with legal proceedings led by a city judge according to Riga’s city law.

At this time, Riga was surrounded by a city wall featuring 25 towers and gates, and it had approximately 40 streets. Beyond the walls lay vegetable gardens owned by the Livonian Order, the Cathedral Chapter, and Riga’s townspeople, followed by the patrimonial district—the city’s rural territory.

The main road into the city was the Sand Road, entering from Vidzeme past the Powder Tower (then known as the Sand Tower). Inside the walls, Riga featured numerous shops and stalls: bakeries, butcher stalls, fish markets, wine sellers, and even three brothels located in the Alder Marsh area (now Vecpilsētas Street). Property in the city was owned by a variety of entities: the City Council, private citizens, the Order, the Archbishop’s vassals, clergy, guilds, and church institutions. The Archbishop himself owned a palace and estate within the city. The first suburbs developed near the Rīdzenes River and port area, as well as on Rīdzenes Island (now Latgale Suburb).

By the 14th century, the city councillors were no longer elected by citizens; instead, the office had become a lifetime appointment. When a councillor died or resigned, the Council itself appointed a replacement from among the city’s wealthiest merchants—making Riga’s governance effectively oligarchic.

The Riga City Council secured independent domestic and foreign policy. Riga was a member of the Hanseatic League, signed treaties with foreign powers, was represented in the Livonian Landtags, waged war against other landowners, maintained its own army, and was, after the Livonian Order, the second strongest military power in the territory of Latvia.

One of the most important city officials was the city judge (advocatus, voget), who adjudicated all criminal and civil cases in Riga and its countryside. Since the mid-13th century, the City Council elected the judge, with the Archbishop only confirming the choice.

A large class of officials and servants also developed, organized into guild-like brotherhoods. These employees received wages in money and grain, were exempt from citizen taxes and militia duty, and often granted housing. For instance, in 1366, the Council employed a weaponsmith from Danzig, who was paid to produce four new crossbows per year and repair the old ones.

The majority of Riga’s inhabitants were of German origin. The official language for business, writing, and governance was Middle Low German. Citizens followed the law and customs of German cities. Alongside the Germans lived Livs, Letts, and other non-Germans, who by the first half of the 15th century made up around one-third of the population. The term “non-German” (unborger) first appeared in 1386, referring specifically to urban inhabitants, not rural ones.

Due to strong trade relations with Rus’, many Russian merchants settled in Riga, establishing their own district with a street, shops, guild hall, and Orthodox church. Riga also saw regular visits from Estonians, Lithuanians, and others.

In terms of social structure, Riga had four clearly defined estates:

  1. Clergy – including canons of the Cathedral Chapter, priests of many churches, monks, and nuns.

  2. Merchants – the city’s wealthiest and most influential citizens, who formed the City Council and controlled all domestic and foreign trade. Their corporate body was the Great Guild.

  3. Craftsmen – mostly German townspeople who either ran their own workshops or were journeymen/apprentices. They organized into guilds (Zünfte), acting as professional associations.

  4. Servants and wage laborers – including both free and unfree individuals. Those who were free could become citizens; those who were not had no such rights.

This hierarchy reflected the medieval urban ideal: “preachers, merchants, workers, and servants” (predicatores, mercatores, laboratores, servitores).

By the 13th century, Riga had acquired the right to mint its own coins, though as of 1356, minting had not yet begun. In that year, the City Council responded to Pope Innocent VI regarding the Archbishop’s rights over Riga’s towns, stating:

“Riga’s citizens have the right to mint coins and set the fineness, but the Archbishop’s seal must appear on the coins,”
adding:
“So far, however, no one has seen a coin minted in the city.”

Nonetheless, the Riga Mark became a recognized currency unit across Livonia, Russia, Hanseatic cities, and Visby.

The City Council managed all financial and military matters. Between 1348–1361, it spent 165 marks on defense. In 1368, during the Hanseatic wars against Denmark, the Council collected 376 marks via an emergency tax to fund a military contingent, compared to 520 marks from all other Latvian Hanseatic cities combined.

There is no evidence that the city maintained professional mercenaries in the 14th century. However, the 1399 “Citizens’ Decrees” state that every male citizen had to personally own full combat gear: a helmet, breastplate, gauntlets, and a battle axe.

Riga’s trade was both transit and import/export oriented. From 1286 to 1352, major exports included: wax, flax, rye, barley, malt, oats, and furs (squirrel, ermine, hare, lynx), as well as tallow, ashes, timber, hemp, honey, and horses. Imports included salt, wool fabrics, table linens, saffron, and sulfur.

Riga had several guilds:

  • Originally one Guild of the Holy Spirit, which in 1354 split into the Great Guild (for merchants) and Small Guild (for craftsmen).

  • In the early 15th century, the Guild of Marksmen was established (kumpany unde broderschap der schutten in der vorgen stadt tho Ryge), including members from both other guilds. They owned a target range and engaged in archery and shooting at wooden parrots, as was custom in Europe.

  • The Brotherhood of Blackheads appeared around 1352; one record notes 7 eras spent on repairing their meeting room. Around this time, their patron saint changed from St. George to St. Maurice.

Although not citizens, the Blackheads were known for their social and cultural life, rather than political engagement.

A Century in Events

A Century in Events: Livonia in the 14th Century

The best insight into 14th-century Livonian events comes from written historical sources. Among these, the Chronicle of Livonia by Hermann von Wartberge, chaplain to several Livonian Masters (residing in Livonia from 1364 to 1385), stands out as especially valuable. Also noteworthy is Balthasar Russow’s “Chronicle of the Province of Livonia”—written two centuries later—which, although more literary in nature, contains many interesting narrative accounts. Additional key sources include castle inspection records, administrative acts, fief registers, and various financial documents issued to individuals.

During the first half of the 14th century, the concept of a Livonian Confederation began to take shape—both among Livonia’s own rulers and in the eyes of external observers. The first assemblies of Livonian city representatives occurred in the early part of the century, although the first written record of a Hanseatic city assembly in Livonia dates to 1350. Meanwhile, hereditary succession (mantāgi) for the Archbishopric’s vassals had been taking place since the century’s outset.

Throughout the entire 14th century, warfare was ongoing both within Livonia and along its borders. Following the conquest of Semigallia (Zemgale) in 1290, Lithuania became the Livonian Order’s primary target of military expansion, as the Order sought to unite its Prussian and Livonian branches.

At the beginning of the century, the city of Riga and the Archbishop of Riga actively used Lithuanian military aid, frequently inviting the Lithuanians to invade Livonian Order territory and joining in military campaigns against the Order. However, after the signing of the Mīlgrāvis Treaty on March 30, 1330, Riga nominally withdrew from such collaboration. In response, the Livonian Order launched retaliatory campaigns deep into Lithuania.

By the end of the 14th century, Livonian Order forces—acting alone or together with troops from the Teutonic Order’s Grand Master in Prussia—had invaded Lithuanian territory more than 50 times, often reaching as far as Kaunas, which was burned down three times.

In turn, the Lithuanians, under rulers Vytenis, Gediminas, and Algirdas, repeatedly invaded Livonia, starting around 1330. These raids also affected lands belonging to the Archbishopric of Riga and its vassals. This continuous warfare was interrupted only briefly—by the Peace of Salynas, signed on October 12, 1398, between Grand Master Konrad von Jungingen (also on behalf of the Livonian Order) and Grand Duke Vytautas of Lithuania.

By this treaty, Vytautas agreed to cede part of Samogitia “for all eternity,” thereby enabling the Teutonic Order’s long-desired territorial unification between its Livonian and Prussian branches.

A second major source of conflict throughout the century was the Livonian Order’s persistent attempt to incorporate the Archbishopric of Riga. As a result, for most of the 14th century, Archbishops of Riga resided in the Papal Court, or—if more politically astute—sought transfer to other dioceses.

A Century of Events Through the Eyes of Chronicle Authors

Master Bruno began his rule in 1296.
During his tenure, war broke out between the Order and the third Archbishop of Riga, Johannes von Fecht, along with the entire cathedral chapter. The bishop and the diocese allied with the pagan Lithuanians and other non-Christians against the Teutonic Order, inviting them into their territory. On 30 September 1297, the citizens of Riga, together with the Lithuanians, burned down the Livonian Order’s castle and convent—structures that had stood since the founding of the Sword Brothers. They also destroyed Berthold’s mill. Using trickery and disguises, the allies captured Karksi Castle, burned it, devastated the surrounding area, and killed around 1,500 people.

On 1 June 1298, both armies met near the Gauja River in the vicinity of Turaida. The bishop’s forces, alongside the pagan Lithuanians, emerged victorious. Master Bruno and 60 knights of the Order were killed in battle, with the total number of casualties reaching about 3,000 men. The Lithuanians built a castle at the entrance to Riga. Emboldened, the bishop’s forces and Riga’s citizens, together with the Lithuanians, besieged the Order’s castle at Ādaži. However, they suffered a crushing defeat on 29 June. Around 400 citizens of Riga perished—many were killed, and many drowned.

Gotthard Rogge was elected Master in 1299, during the war with the Bishop of Riga. There was peace with external enemies, but the conflict with Riga and the Archbishop continued until 2 July 1307. After a battle with the Lithuanians near Riga, the Master agreed to a truce with the city. On 23 May 1305, the Cistercian Order sold its monastery in Daugavgrīva to the Livonian Order and relocated to Padise.

Konrad Jock became Master in 1307.
In 1313, the Order rebuilt Daugavpils Castle. That same year, pirates from Riga plundered the parish of Kilegunde in Saaremaa. On their return, a storm drove them ashore near Dundaga, where the Ventspils commander captured them and hanged them by their feet from trees. This act led the citizens of Riga to accuse the Order of brutality before the Roman Curia, but Pope Clement V dismissed the charges.

According to Balthasar Russow, in 1315 there was a severe famine in Livonia and surrounding lands. Grain and food prices became so high that hundreds died of hunger and were buried in mass graves. Some parents killed and ate their children; others locked them in heated saunas to suffocate them due to the lack of bread. In one Estonian village, a son killed his father and tried to eat him but was caught and tortured to death. When thieves were hanged, poor people would remove their bodies at night and eat them. The famine and high prices lasted three years and were caused by repeated crop failures due to frost.

On 24 April 1316, during the truce, the people of Riga attacked and completely burned the outer bailey of Daugavgrīva Castle, killing a knight of the Order and several servants. Thus began the second war between Riga and the Order. On 25 July 1319, the Master and the commanders of Viljandi, Ventspils, and Daugavgrīva received papal confirmation in Avignon of their rights to Daugavgrīva’s property. In 1321, the Order built a new castle in Mežotne to secure the border against the Lithuanians. In 1323, the new vice-master Berthold von Kesselhut arrived from Prussia and led a large army to Pskov, capturing and looting the city and bringing back rich spoils.

On 1 June 1324, with Riga’s mediation, Lithuanian ruler Gediminas made peace with the lords of Livonia. Riga’s citizens and Gediminas played a peculiar role in these events. On 4 April 1324, at the order of Archbishop Friedrich, the Livonian Order was excommunicated during a ceremony in Riga Cathedral, with bells ringing and candles extinguished. It’s possible that the provost of the cathedral chapter, Ludfrid, had no part in it. However, on 4 April 1326, he was murdered in his chamber in Riga.

Eberhard von Monheim, commander of Kuldīga, a devout and upright man, became Master in 1327 and did much good for Livonia and the Order. During his rule, war broke out again with Riga’s citizens. On the night of 23 June 1328, the people of Riga attacked Daugavgrīva Castle, burned the village and church around it, killed more than 100 people, and inflicted damages worth over 400 marks. In September of that year, Riga sent two aldermen and two citizens to Lithuania, promising to hand over all the castles and fortresses of the diocese if military support was provided. In September 1329, Lithuanians invaded Livonia with Rigan guides, caused 6,000 marks in damages in the Estonian lands of the Order. That same year, the Master besieged Riga and blocked all supply routes, forcing the city to sue for peace. On 30 March 1330, Riga surrendered the city, all its rights, freedoms, and privileges to the Master, and demolished its walls and gates. This occurred on St. Gertrude’s Day. The Master granted the citizens new rights and privileges and built a new castle at the former site of the St. Spirit Convent by the Daugava. The destroyed site was handed back to the convent, which had functioned as a hospital and shelter.

Between 1331 and 1333, the Order launched raids into various Lithuanian regions and in 1334 into Polotsk. In 1335, the castles of Dobele and in 1339, Tērvete were built.

Burkhard von Dreileben became Master on 24 June 1340.
On the Feast of the Annunciation (25 March), he began constructing Vastseliina and Frauenburg castles on the Russian border. According to Balthasar Russow, Russians attacked Alūksne intending to suffocate the Germans with smoke, but the Germans bravely resisted and killed 82 Russians. Arnold von Vietinghoff became the first commander of Alūksne.

In April 1343, while the Master was campaigning against Russia, a major Estonian peasant uprising erupted on St. George’s Night (22 April) in the Diocese of Reval. According to Russow, almost all Germans—nobles and commoners, young and old, women and maidens—were massacred. Monasteries were also attacked. In Padise, 28 monks were killed. The uprising spread through Harju, Läänemaa, Virumaa, Saaremaa, and across Estonia. Thousands fled to castles. Around 10,000 peasants joined the revolt and besieged Reval. In Saaremaa, peasants killed all the Germans and besieged Pöide Castle. After being promised safe passage, the garrison surrendered but was murdered. Arnold and priest Johann were stoned. Peasant envoys even asked Swedish bishops for help. Meanwhile, the Danish governor of Reval requested aid from the Master, who promptly arrived with his forces. Many peasants were killed, and near Reval, nearly 10,000 were slain. The Danish governor thanked the Master and asked for support against the expected Swedish arrival. Reval and its castle were entrusted to Goswin von Herike, commander of Viljandi.

After this, the Master marched to Haapsalu to aid the bishop and nobles. When the local peasants heard of the Master’s approach, they fled into the forests. Finnish reinforcements arrived from Vyborg but, learning that the rebellion had been crushed, made accusations against the Danes instead. Goswin and the Danish governor hosted them politely and sent them off with promises. Elsewhere, peasants encouraged the Russians to attack Livonia again. Russians invaded the Diocese of Dorpat, but the bishop’s forces, together with some from the Order, defeated them near Otepää, killing over 1,000 men. Several nobles and knights fell, including Johann von Levenwolde.

In response, Master Dreileben led two punitive winter campaigns against Saaremaa in 1344 and 1345. During the first, the rebels’ stronghold was destroyed and their leader Vesse killed. The second resulted in a peace agreement.

While the Master was in Saaremaa, on 20 February 1345, a Zemgalean named Pale betrayed the Order and let Lithuanians into Tērvete Castle. They killed 8 knights and many others. The attackers then marched to Jelgava, set fire to wooden buildings, and flames reached the castle. Around 600 people died. The Lithuanians advanced to Riga, camped there, then moved to Ādaži and Sigulda, where a Liv chief offered to help conquer all Livonia but was beheaded by King Algirdas.