Holy Cross Exaltation Monastery, a historic landmark of Poltava, is located on the southern edge of a long range of hills overlooking the western bank of the Vorskla River, and can be seen from a considerable distance. This location was chosen for the monastery by Father-Superior Kalistrat of the Mhar Monastery in Lubny (200 km northeast of Kyiv, Ukraine's capital). Because Ivan Iskra, Ivan Kramar and other officers of the Poltava Kozaks regiment, together with Regimental Commander Colonel Martin Pushkar, established the monastery in 1650, it can be regarded as a Kozak monastery. Following its foundation numerous Tatar raids repeatedly plagued Poltava as well as other cities of eastern and central Ukraine. Orthodox monasteries, constructed out of wood, were especially desirable, and the Holy Cross Exaltation Monastery was robbed and razed to the ground many times. After it was burned once again in 1695, the decision was made to rebuild the monastery in stone.
    At the time of the Battle of Poltava, the decisive battle of the Great Northern War (1700-1721), the monastery had not been completely rebuilt.
  On the eve of the battle (June 27, 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 one of the monks' cells. The main building of the monastery, the Holy Cross Exaltation Cathedral, was finished and consecrated in 1756. Its construction was funded by Colonel Vasiliy Kochubey, a local landowner. This cathedral, created in the Ukrainian Baroque style, has two altars: the main altar is known as the Holy Cross Exaltation altar, and the side altar is dedicated to the Annunciation of the Blessed Virgin. In the middle of the 18th century the famous wood carver Shalmatov created a unique, elaborately carved high iconostasis. Unfortunately all of the painted icons and the entire wooden iconostasis were destroyed in the Revolution of 1917. In addition to the Cathedral, the monastery had a single-cupola refectory church, the Church of the Holy Trinity, which had been built in 1750. However, by 1887 this church had fallen into disrepair and was demolished. The building of a new refectory church dedicated to Saint Simeon was made possible in 1887 by funds donated by the Siberian merchant Kotelnikov in memory of his son, who had died in Poltava not long before and was buried in the cemetery near the monastery. Kotelnikov also built a dwelling house for the monks and a hospital. The Holy Cross Exaltation Monastery was well known for its beauty, richness and the great number of monks who lived here.
    In 1775, the 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, a well-known theologian and orator. He is buried in one of the monastery’s crypts. The monastery’s 45 meter high Bell Tower was built near the entrance gate in mix of Baroque and Classical styles. It was consecrated in 1786 by Archbishop Nikifor Feotoki. Its majestic construction resembles the Bell Tower of Kyevo-Pecherska Lavra church in Kyiv. The middle tier of the bell tower used to contain an altar in the name of the Icon of the Blessed Virgin. Its miracle-working icon of the grieving Blessed Virgin was famous for its ability to cure people of many diseases. Before the Revolution of 1917, the tower contained many bells placed at different level, including one bell, cast in 1797, that weighed about six tons. During the years immediately following the Revolution (1917-1921), when power in the city changed hands many times, the monastery was repeatedly plundered. The oak woods surrounding the monastery were completely cut down and in 1923 the monastery was closed and turned into a club for railway workers.
    During the time of Stalin's campaign against religion many churches were razed to the ground and 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 shelter for homeless children, and later as a hostel of the Poltava Pedagogical Institute.
  During the German occupation it temporary resumed its activity as a convent. Another attempt to reopen it was made in the 1950s; however, in 1958 the monastery was closed by decision of the Executive Committee of the Poltava Region. All nuns were removed to other convents or forced to return to their families, and all crosses were dismantled. Only after the collapse of the Soviet Union in the early 1990s did the Holy Cross Exaltation Monastery resume its activity as a parish of the Orthodox Church of the Moscow Patriarchy. For several centuries the monastery was the site of a cemetery for Poltava’s citizens. To commemorate the cemetery that had been destroyed in the 1930s, a memorial was erected near the entrance to the cemetery, which contains remnants of some of the old headstones from the cemetery.