How can I get historic flight data by N-number?
Some websites offer historic flight records, but they are not free. And they don't go back for decades and are not complete.

If you really must, try the FAA Registry, see if the owner is listed, and get in touch if their contact information is listed.

The FAA only keeps broad records, as this answer explains.

Don't get me wrong, but it's like asking where a car has been to for the past 20 years. But I could be mistaken.