Be sure to book your train trip early. There are only 6 slots on the train for RORO. You will need to hang your bike. So have the bags off when the train rolls up. As I recall the bike car will be behind the sleepers which is behind the baggage car which is right behind the engine. Have a flashlight ready as it is often dark inside the car. Coming from Cumberland and only going to Connelsville, there are only a couple of stops so I would not be too worried about security. If you are have a lock ready. Amtrak will supply the cable.

If you can get into Connelsville early for the start of the trip you could make Rockwood that night. Stay at the hostel. Next day would be Cumberland. If you get in early, and it is the weekend, you could take the stem train back up to Frostburg and do that section all over again.

If you can't make it early into Connelsville then a good first night stop would be Confluence.