On December 17, 1941, Nazis rounded up a group of around 500 able-bodied men and transported them out of the Yalta Ghetto to the Massandra Vineyards, where they were ordered to dig deep trenches at the bottom of the 4th ravine, which was used as a reservoir. When they completed their work, they were shot and thrown into the trenches they had just dug. One day later, on December 18, 1941, the remaining Jewish population of Yalta were told they were being resettled, but they were removed from the ghetto and transported to the Massandra Vineyards' 4th ravine, where they were shot in groups of 5 and thrown into the ravine. Many of the victims were still alive when they were thrown in, causing them to drown. At the end of this day, the Nazis completely filled in the ravine, and later bombed it in an attempt to destroy evidence of their crimes. 1,500 Jews died in total. The local gentile population of Yalta, horrified and grief-stricken, covered the burial site in beautiful flowers shortly after the massacre, which angered the Nazis.

In 1969, the Soviet government erected a modest monument to the victims of the Massandra Vineyards 4th Ravine massacre, but the monument didn't acknowledge that the people killed were Jews. In December 1999, the Jewish community of Yalta erected a new monument near the old one, this one making it clear that the people murdered there were Jews. Every year on May 9th and December 18th, the Jewish community of Yalta gathers at the memorial site to pray for and honor the victims.