Holly Cross Exaltation Monastery, an outstanding historic landmark of Poltava is situated on the southern edge of the long range, overlooking the western bank of the Vorskla River and can be seen from considerable distance. This location was chosen for the monastery by the Father-Superior Kalistrat of Mhar Monastery (situated in Lubny, 200 km. away from the Ukraine's capital, Kyiv). The commanders of the Poltava Cossacks regiment Ivan Iskra, Ivan Kramar and others, headed by regimental commander Colonel Martin Pushkar, founded it in 1650, so it can be regarded as a Cossack's monastery.

In the centuries to come, numerous Tatar raids repeatedly plagued Poltava, as well as other cities of eastern and central Ukraine. Wood constructed orthodox monasteries were a subject of desire for invaders; it was robbed and razed to the ground many times. The last time it was burned was in 1695 and then the decision to build a monastery in stone was made.

By the time of the decisive battle of the Great Northern War (1700-1721) this monastery had not been completed. On the eve of the battle of Poltava (June 27th 1709) the main part of the Swedish infantry was deployed around the monastery and the Swedish King Charles XII had his headquarters inside the monastery in a monk's cell.

The building of the main Holy Cross Exaltation cathedral was funded by Col. Vasiliy Kochubey and was finished and consecrated in 1756. This cathedral, created in Ukrainian baroque style, has two altars: the main alter, in the name of Holy Cross Exaltation and the side alter, in the name of the Annunciation of the Blessed Virgin. In the middle of eighteenth century the famous carver Shalmatov created a uniquely carved high iconostasis. Unfortunately all uniquely wall painted icons and wooden iconostasis were destroyed after the revolution of 1917.

In addition to the Cathedral, there was a single-cupola refectory church in the name of Saint Trinity built in 1750 however, by 1887 this church had fallen into decay and was demolished. The building of a new refectory church in the mane of Saint Simeon was funded in 1887 by Siberian merchant Kotelnikov in commemoration of his son, who had died in Poltava not long before and was buried in the cemetery near the monastery. He also built a dwelling house with monk cells and a hospital. The Holy Cross Exaltation monastery was well known for its beauty, richness and a great number of monks who lived here.

In 1775, Russian Empress Katherine II ordered all Slavonic and Kherson Archbishops to make the monastery their residence. One of the most famous among them was Archbishop Amvrosiy, known for his theological works and speeches. After his death his body rested imperishable in a monastic crypt.

The 45 meters tall Bell Tower was built near the entrance gate in mixed baroque and classic style. It was consecrated in 1786 under the Archbishop Nikifor Feotoki. Its Majestic construction resembles the Bell Tower of Kyevo-Pecherska Lavra in Kyiv. In the middle tier of the bell tower there was an altar in the name of the Icon of the Blessed Virgin. A wonder-working icon of mourning Blessed Virgin was famous and widely respected for its unique ability to cure people of many diseases. Before the revolution of 1917 there were many bells placed at different levels and the weight of the heaviest one, cast in 1797, was about six tons.

During the anxious time of 1917-1921 when power in the city had been changed many times the monastery was repeatedly plundered. Monastic oak-wood construction was completely cut down and in 1923 the Holy Cross Exaltation monastery was closed and turned into a railway men club. In the time of Stalin's struggle against religion many temples were razed to the ground and almost all priests were ruthlessly persecuted or executed. This monastery was lucky to avoid the tragic fate that many other churches met. In the 1930s it was used as an orphanage and homeless children shelter and later - as a hostel of the Poltava teachers training institute. During the German occupation it temporary resumed its activity as a nunnery. Another attempt to renew its activity was made in 1950s but in 1958 it was closed by the decision of the Executive Committee of Poltava region. All nuns were removed to other nunneries or forced to return to their families and all crosses were dismantled. Only after the disintegration of the Soviet Union did the Holy Cross Exaltation monastery resume its activity as a parish of the Orthodox Church of the Moscow Patriarchy.

Near the entrance there is a memorial stone, which was erected in commemoration of a larger cemetery that was razed in 1930s. Many famous city inhabitants were buried there and some of the remained gravestones were set in this monument.