The first references to the village of Cieszanów date back 1496. After the foundation of Zamość in 1580 and the opening up of a trade route from Jarosław, the area became more attractive, as evidenced by increased settlement. Its favourable geographical conditions were used by Stanisław Cieszanowski from Cieszanowice, Jelita coat of arms, the starost of Sambor, who purchased part of estate in Nowe Sioło. As the owner of the villages of Podemszczyzna, Łówcza and Chotylubia, he strove from that moment on to consolidate his properties and strengthen the position of his family. Consequently, he started efforts to obtain a charter for the town. He achieved his goal in 1590, when Cieszyn was officially founded under the Magdeburg Law.

At the turn of the 17th century, the population of Cieszyn engaged mainly in agriculture, crafts and trade. Most inhabitants worked as shoemakers, furriers and weavers. There were also blacksmiths, locksmiths, carriage-builders, carpenters, coopers, bakers, butchers, maltsters, brewers, ropemakers, a slime maker, a potter and a gunsmith. In 1593, a paper factory was set up in Cieszanów. The town had also its mill and brewery. Since a major trade route linking Lviv with Gdańsk passed through Cieszanów, the town was an important craft and trade centre, a position that contributed to its growth at the time.

After the death of Stanisław Cieszanowski, the town became for a short period of time the property of the Wierzbicki family, Nieczuja coat of arms. In 1637, it was taken over by Jan Bełżecki, Jastrzębiec coat of arms, who purchased also Nowe Sioło and Chotylub. After his death in 1642, the estates were passed on to his eldest son, Aleksander Stanisław, who held the office of the Podole Voivode. The development of the town was stopped by epidemics of infectious diseases, fires and destruction wreaked by domestic and foreign armies. In 1648, the town suffered as a result of the invasion of Chmielnicki's Cossacks. In 1655, it was plundered by the Swedish troops; in 1672, in turn, it was looted by the Tatars, who were soon defeated by Jan Sobieski. A year earlier, in 1671, the troops of the Crown heading to Czorsztyn, where Aleksander Kostka-Napierski took refuge after the Battle of Berestechko, marched through Cieszanów. In 1681, Jan III Sobieski, as a king, confirmed the municipal rights of Cieszanów and added a feathered helmet, banners, swords, barrel cannons and bullets to the town's coat of arms.

In 1772, following the first partition of Poland, Cieszanów was incorporated into Austria as part of the Tomaszów Poviat in the Bełżec District. Subsequently, the town was included in the Żółkiew District. The town was owned for a short period of time by Jan Zamojski, who purchased also the villages of Nowe Sioło, Chotylub and Łówcza. At that time, a brick factory was established in the town.  After the dissolution of the Dominican Order in 1788, the local parish was taken over by the secular clergy and the folwark was sold. The abolishment of serfdom came in 1828, when the town remained in the hands of the Rojowski family, Cholewa coat of arms, which became also the town's coat of arms. In 1785, Cieszanów had 1,462 inhabitants. By 1801, their number rose to 1,534.

Cieszanów was indirectly involved in the national uprisings. In 1809, the troops of the Duchy of Warsaw passed through the town. During the January Uprising of 1863, arms, ammunition, bandages, and volunteer soldiers were sent via the town to Galicia. Moreover, it was in the town that the biggest hospital in Galicia was set up in May 1863 for soldiers wounded in the Battle of Kobylanka. Dead insurgents were buried in the local cemetery. During the uprising, a squadron of Hungarian hussars was stationed in the town to keep order near the frontier. In 1883, the construction of a monument of Jan III Sobieski was financed. It was unveiled during a solemn ceremony on the fiftieth anniversary of the Battle of Kobylanka, in the forest beyond Nowy Lubliniec. Polish cultural, social and sporting life also thrived in the town.

In 1871, a branch of the Polish Association of Education was established. Moreover, in 1879, the Voluntary Fire Brigade started to operate. Among organisations founded at a later time, one should list the Casino Association with a library, Charity Society (1884), "Gwiazda" Townspeople Association (1904), "Sokół" Gymnastic Association, as well as scouting, self-defence and shooting teams. There were also other organisations, most notably a club of the Polish People's Party. In 1904, the Credit Society started to operate, followed by the Savings and Loan Company. The town experienced its heyday also in the area of education. Cieszanów had a five-grade folk school, attended by children from the neighbouring villages and towns. They could continue education at high schools (Jarosław, Lviv and Przemyśl) and universities (Kraków and Lviv).

Following the outbreak of the First World Word, the development of Cieszanów was stopped. On 9 September 1914, the Austro-Hungarian troops were twice defeated in the Battles of Komarów and Zamość and started to withdraw. On 11 September 1914, the Soviet Army entered Cieszanów and stayed in the town until 18 June 1915. The Russians destroyed all shops and Jewish workshops in the town. During the hostilities, the town was burnt and the county authorities were temporarily relocated to Lubaczów.

After the end of the war and fall of the Austro-Hungarian Empire, the Ukrainians took power over the town on 1 November 1918, having disarmed the Polish Security Guard and arrested the organisers of the town's defence, whom they shot to death in Niemirów. Cieszanów was liberated on 6 November 1918, when the Ukrainian units surrendered to the Polish Legions commanded by General Jarosz, and became an administrative part of the Lviv Voivodeship. In 1919, the country authorities returned to Cieszanów. It was decided, however, to relocate their seat on a permanent basis to Lubaczów, where they took office on 1 January 1923.

According to the first general census, Cieszanów had 2,282 inhabitants. The town continued to be a major centre of cultural life with various social and political organisations. It was the seat of a magistrates' court, branch of the tax office, third-degree common school, post office, cadastral office, health maintenance organisation and other institutions. In 1921, a factory of carriages started to operate in the town under the name "Agra". Additionally, Ciechanów had 2 functioning mills, 2 groat mills, 1 oil factory, 5 warehouses, 7 restaurants, 2 hotels, as well as numerous shops and craft workshops. The Stefczyk Credit Union operated in the town as well  (created after a merger with the Savings and Loan Company). The town authorities managed also to open a teachers' seminar, which helped many young people to receive education and a profession in the years 1925-1932. In 1939, there were 3 doctors, 1 veterinarian and several advocates and notaries in the town.

A week after the outbreak of the Second World War, on 7 September 1939, the first German bombs were dropped on Cieszanów. On 12 September, the Germans entered the town and arrested its mayor - Bolesław Bajorski, the Secretary of the Municipal Board - Jan Kopf, as well as the director of the local school - Kazimierz Kaleciński. After they had withdrawn from the town, Cieszanów was occupied for a short time by soldiers of the Red Army. Subsequently, after the Russians had left the town, a demarcation line was established. Jews were sent to an area assigned to the USSR. Cieszanów was incorporated into the General Governorate, a territory occupied by the Third Reich, as an administrative part of the Tomaszów Poviat and, after its liquidation, of the Zamość Poviat  (Lublin District). The town became the headquarters of the border guard and army, which started to build a strategic road from Zamch to Żuków in the spring of 1940.

 At the time, the Germans destroyed the Jewish cemetery to use tombstones in the construction of the road. They set up a forced labour camp, whose Jewish prisoners were required  to dig border reinforcements. The Germans built also a ghetto around the synagogue in Cieszanów, where they placed Jews from  the surrounding villages.  After the outbreak of the German-Soviet war in June 1941, units of the Wehrmacht left Cieszanów for some time. In early 1943, the Germans deported all the Jews to Wierzbica, where they were shot to death in a forest. The neighbourhood of Cieszanów was also a place of activity of Polish guerrilla units. There were two posts of the Home Army in the town itself. In the spring of 1944, feeling threatened by the Ukrainian Insurgent Army, Polish inhabitants started to leave the town to escape beyond the San River. On 2 May 1944, partisans evacuated most of the remaining population to Ruda Różaniecka. On the night of 2 to 3 May, Cieszanów was burnt to the ground by units of the Ukrainian Insurgent Army. The villages of Kowalówka and Dolina shared its fate. In July 1944, Cieszanów was seized by the Soviet Army. Its first mayor after the war was Paweł Lisowski[1.1]].