The roof was 18 yrs old. Had some cupping, curling and some splitting but I’m not sure what the holes are. At first I thought woodpeckers maybe, but woodpeckers around here make bigger holes and usually in the siding not the roof.
Try powderpost beetles
http://www.uky.edu/Ag/Entomology/entfacts/struct/ef616.htm
I didn’t think those affected cedar shakes. More of a hardwood problem aren’t they?
I have yet to see an infestation like the shingles pictured. Usually I will find Powder Post beetles in the crawl spaces and occasional stump but never on a roof. It has something to do with the right level of humidity in the wood. Also most powder post beetle holes are very fine.
//Rick
Hi James,
I am with Claude, deffinately some type of boring insect/worm/creepy crawly 
That roof was probably installed with a lowish grade of shake and will be needing replacement soon rather than later.
Regards
Gerry