cherries will ripen as a cluster starting at the most terminal tip, and getting greener up the cluster. It’s flowers are arranged in a raceme, which means the most mature flowers are at the tip.

practically speaking, with cherries, I’ll usually wait till the tip most one is “very ripe”, and usually the middle is perfect and the base is a bit under ripe. but I prefer having that range. alternativly, wait for them all to ripen in the vine