Dave,
I live and hunt in "bear country," eastern Allegany County. Since the bear hunt started I've been able to hunt four or five years either on my tag, my wife's tag or other hunter's tags (if I recall correctly). Most people think MD bear hunt = Garrett County and while that is pretty true, Harry Spiker, DNR's bear biologist dude, calls western Allegany County around Dan's Mountain Maryland's "bear incubator." So don't lock yourself in to the "Garrett County only" mindset.
I've hunted in both counties on public and private. I take the rifle as the tag's are so coveted, I want to KNOW I will probably hit what I'm shooting at! No matter where you hunt, the biggest thing is: you HAVE TO SCOUT. Yea you can dumb luck in to a bear, especially in areas with a decent concentration of bear. But overall, you'll need to put down some boot leather.
Hope that helps!
Matt