We attempted to make a relaxed start out of Cumberland, because the day's mileage plan was light, the weather forecast was good, and we'd pushed the group the previous day. At 0800 we hit the bike shops etc along the Canal, and shortly after that a rather drawn-out loading process began. Some experienced bicyclists saw this as an opportunity for a bike-nap.
As the PackEx progressed I went over to watch another group of bicyclists packing and made small talk, they were a group of upstate New Yorkers riding Pittsburgh to DC, very nice people. They gave me a home made snack bar to try and we discussed trail trivia. We would meet them on-and-off for the next few days.
We rode for a few miles along the C&O and somebody said to me, I can see what you meant about this being a rough trail, and I replied "but it's the best I've ever seen it". The C&O was much drier than it usually is.
We stopped at Oldtown and visited the Schoolhouse Cafe, which was excellent as always, cheeseburgers and sandwiches and great pies. We saw the NewYork tour group again and became a bit better acquainted. When I was at the Schoolhouse Cafe a month ago on another ride they were sheltering three abandoned kittens at the other end of the building and they looked pretty fragile, I was glad to see that two of them had survived and were thriving.
Back on the trail and rode to the Paw Paw Tunnel, which went well. A few miles south of the tunnel, around MP153 one of the riders' rear derailleur snapped off the bike and jammed into the spokes, it was a pretty major snafu and the bike wasn't rideable. We were out of cellphone coverage and it took a while to get assistance to the bike.
Fortunately, a local couple passed by the rider and bicycle and offered him a lift in their pickup, God bless them, and delivered him to Bill's Place in Paw Paw and our sag wagon (PerkyMobile™). Although we thought the bike might be done for as far as this ride went, the rider went off in the van to C&O Bicycle in nearby Hancock. C&O Bicycle was able to replace the derailleur hangar but the staff on hand was unable to help more than that (it was late in the day). K made a phone call to Cumberland Trail Connection Bikes and they were good enough to offer some advice over the phone, and with his mad skillz he was able to fix the derailleur, true the wheel, and adjust the brakes; it was very impressive and he was back in the ride.
In the meantime, there was a frustrating interaction back in Little Orleans with our lodging. We had made reservations with Town Hill B&B, which is located a significant distance away from the trail but they provide a shuttle service for riders and bikes so we went for it. When our riders came off the trail and called the B&B for pickup, the B&B told them "no, eat dinner first and then we'll come and get you". Our people wanted to shower and clean up and then eat, but the B&B staff wouldn't do it. That was not our expectation and it was a real disappointment, but we really didn't have any other options.
The NewYork contingent attempted to ride up the hill, we passed them in the van as we were riding to the bike shop, they were awesome and making a killer effort.
Later, after our folks ate (as instructed) and took the shuttle to the hotel, the staff was charging $6 for the ride up and another $6 for the ride down, and that was unexpected and seemed like gouging at a place charging $150 and above for a room. Plus they threw the bikes on a trailer, people's wheels ended up entangled with other people's pedals, it wasn't good. I must note that the next day's breakfast the was wonderful, but it wasn't wonderful enough to cover the downside.
The Town Hill B&B was beautiful, historic, it looks like you could restage The Shining in the dining room, but it is not in any way a place for bicyclists. Their view of our arrangements was completely different from our understanding, and they had no flexibility. I spent $150 (which would be OK for a positive experience) and I feel like I was taken. Bottom line, in our opinion: The Town Hill B&B in Little Orleans is not a place for trail riders.