This trip plan is for a Pittsburgh-based rider. It assumes you can persuade somebody to give you and your bike a lift to Cumberland MD, in a pickup or a van or a car with a bike rack. You could also use Greyhound or a shuttle service.
Day One: Cumberland to Meyersdale
Depart Pittsburgh 0500, get a lift to Cumberland MD
Take the 1100 Cumberland (MP150) bike-train up the hill to Frostburg MD (MP16), arriving 1230.
Begin bicycling. Ride uphill to MP22, Mt Savage Vista.
Ride through the Mt Savage Tunnel
Cross the Continental Divide at Mp24, and it's downhill from there.
Stop at Meyersdale (MP32)
Morguen Toole hostel
daily mileage: 16 (includes 8 miles of climbing)
In Meyersdale, breakfast at GI Dayroom
Ride from Meyersdale to Rockwood (MP44)
part-time bikeshop at the Rockwood trailhead
snack stop at Rockwood Opera House
ride 18 isolated miles, which includes the Pinkerton Horn and two scenic bridges
End at Confluence MP62.
Confluence Cyclery bikeshop
dinner at River's Edge Restaurant
I've stayed at River's Edge B&B, River's Edge Loft, and friends have stayed at ParkerHouse.
There's a lot of lodging options.
daily mileage: 30
ride to Point State Mark, MP150
daily mileage: 34
Overall, the lodging is one night in a hostel ($30) and three nights in B&B's. I'll have to follow-up with a camping itinerary.