As in the other areas of East Frisia, the system of the old Frisian freedom in Harlingerland came under increasing pressure due to the rise of the chieftains.

The first to call himself 'Chieftain of Esens, Stedesdorf and Wittmund' was Sibet Attena in 1455; a loyal follower of Ulrich Cirksena, the later founder of the County of East Frisia.

His son, Hero Oomkens, on the other hand, turned away from the Cirksena dynasty and its claims over the entire East Frisian peninsula.

When Wibet turned against the Tom Brok family in the battle for power in East Frisia, his castle in Esens was razed to the ground.

Through struggle, marriage politics and ties with the Cirksena dynasty Sibet Attena had succeeded in getting the entire Harlingerland in his hands.

[1] In the following years, Sibet Attena behaved as an extremely loyal vassal of his cousin Ulrich Cirksena.

Sibet Attena served as Ulrich Cirksena's most important advisor in the early years of the young county.

After Ulrich Cirksena's death in 1466 he supported his widow, Theda Ukena, on condition that the lordships of Esens, Stedesdof and Wittmund would retain their autonomy from the County of East Frisia.

Unlike his father, who had been a loyal vassal of the Cirksena dynasty all his life, he developed into a bitter enemy of the East Frisian counts.

Hero Oomkens tried fanatically to keep his lordships of Esens, Stedesdorf and Wittmund out of the hands of the East Frisian counts.

Hero Oomkens was supported by rulers from the region such as the Prince-Bishop of Münster, the County of Oldenburg and the city of Bremen.

Hero seized this opportunity with both hands to severely damage the Cirksena dynasty and thus strengthen and consolidate his own rule in Harlingerland.

While the East Frisian counts opted for the new protestant religion, the rulers in Esens, Stedesdorf and Wittmund remained fervent Catholics, although this was more for political considerations than religious ones.

In the meantime he had made enemies in Bremen by issuing letters of marque aimed at damaging the merchants of that city as much as possible.

Balthasar lost his rule in these areas and fled to his sister Onna who was married to the ruler of the County of Rietberg.

Charles II of Guelders then invaded the County of East Frisia and caused great devastation and suffering in the area.

Enno II of East Frisia felt compelled to restore Balthasar to his honour and make far-reaching concessions.

They ruled the county of Rietberg and the lordships of Esens, Stedesdorf and Wittmund jointly, initially under the regency of their mother Agnes of Bentheim-Steinfurt.

In order to bind Esens, Stedesdorf and Wittmund to East Frisia once and for all, the Treaty of Berum was drawn up on 28 January 1600.

During the Thirty Years' War, East Frisia would repeatedly fall victim to roving armies looking for an area to winter in.

The lordships of Esens, Stedesdorf and Wittmund had their own institutions and the powerful States of East Frisia had no say in the area.

Enno III had to watch helplessly when the hardships of the Thirty Years' War also reached East Frisia.

When Ernst von Mansfeld occupied his county, Enno III withdrew with his court to the city of Esens.

Enno III's successor, his son Rudolf Christian, underlined the East Frisian rule over Esens, Stedesdorf and Wittmund by incorporating the coats of arms of Esens and Stedesdorf (the bear on a yellow background) and Wittmund (two crossed tournament lances on a blue background) into the coat of arms of East Frisia in 1625.

In order to prevent further conflict, Christine Charlotte, regent of East Frisia, and Anthony Günter of Oldenburg concluded a border treaty in 1666.

With the death of Prince Charles Edzard of East Frisia in 1744, the autonomous position of Esens, Stedesdorf and Wittmund also came to an end.

When the Reformation reached East Frisia, the rulers initially managed to preserve the Catholic character of the area.

This enabled Balthasar Oomkens to form alliances with powerful neighbours such as the Duke of Guelders and the Prince-Archbishop of Bremen.

A strong advocate of this movement was Prince George Albert of East Frisia and his chancellor Enno Rudolph Brenneysen, who came from Harlingerland.

[7] The Christmas flood of 1717, which was experienced as a divine judgment, strengthened the status of Pietism as the dominant religious force.