The Trinity Boldin Monastery is at the old Smolensk road (now it is rarely used) in the environs of Dorogobuzh. The monastery was founded by St. Gerasimus of Boldino (a monk from the Goritsky Monastery of Pereslavl-Zaleski) in 1530. It is the oldest monastery in Smolensk region. Later St. Gerasimus of Boldino also founded the Monastery of John the Forerunner in Vyazma.

The first stone churches were built at the monastery in 1580. The monastery got very rich thanks to donations and vast possessions. However, as the monastery was at the Smolensk road, which was used by the Polish troops in 17 century, the French troops in 19 century and the German armies in 20 century, it was often ruined. At the time of occupations its buildings were used for economic needs. Almost all of them were blown up in 1943 during the retreat of the German troops. 

The relics of St. Gerasimus of Boldino were found during the clearing of the southern aisle of the Trinity Cathedral in 2001. Today the shrine with his miracle-making relics is kept at this cathedral.

In our days all monastery buildings were completely restored: the Trinity Cathedral, the Church of Presentation of the Blessed Virgin with a refectory, a bell tower and the walls of the monastery. The monastery itself is on the shore of a picturesque lake.