Would be neat to meet up and ride the hill country with him.
It would, but can't this weekend.....Memorial Weekend.
Madman - grab a paper map and a highlighter and "connect the dots"....
Midland
Sterling City
San Angelo
Brady
Mason
Fredericksberg (lunch? 250 miles)
Comfort
Boene
New Branfels. (Overnight stop? Total from Midland, 350 miles)