While we are at a point in this thread when both Cumberland and Travel Mapping are being discussed ...
If anyone is planning to add MD 61 to their list, be forewarned that MD 61 is not in Travel Mapping (I don't think it is signed). Found that out the hard way, but since I had four other 61's, it wasn't a big deal. (I put a comment in my list file anyway, so if it ever gets added, I'm reminded to add it).
As for parking - when I took a weekend trip out there to ride the Western Maryland Scenic Railroad, I "solved" the parking issue by staying at the nearby Fairfield Inn, parking my car there as a guest, and walking where I wanted.
(Edited to add:)
If you're also a rail fan (and I know there's some overlap with road fans) I highly recommend the WMSR.