The tool at DNA painter is very useful for this.
The answer for 66 cMs is:
Assuming no pedigree collapse or endogamy, and that you're related in just one way, the furthest back you might need to go to find common ancestors for a match of 66cM is 4th-Great-Grandparent level or generation 7 on your pedigree chart.The connection may be closer.
The same tool gives the probabilities: