My nephew lives out in Keyser WV. Route 50 from Winchester VA to 220 N and Keyser is a good road. 220 from Keyser up to Cumberland is good as well. It is mostly VA though so spirited driving might have associated problems. 50 gets twisty out there though. I had fun when I wasn't behind the geriatric types.
This is a good link run from Frederick MD for the Deep Creek Lake cruise noted above.
Map:
Link from Frederick, MD to Deep Creek Lake run from above