u/In_Cog_Neat_0

Hello kind keepers of gap trail knowledge!

I'll be in Pittsburgh for work in late July, so I figured I might as well take a train and bike home to DC after. I've been wanting to do it for years—carpe diem and all that.

Looking forward to something of a physical challenge, so I'm thinking 5 nights / six days of riding. I'll do some training leading up to it, but I've been riding centuries roughly quarterly for a few years now, so I think I know what I'm getting into.

Here are some questions I'd love opinions on:

1. Since I'm not particularly nostalgic, I'd like to stop and check out a few marvels along the way, but I don't need too many stops. What would be your recommendation for TOP TIER off-the-beaten-path things to see? I'm interested in labor and union history, caves, and cool art.
2. Lodging. My intention is to pack as light as possible, and arrange for lodging, breakfast, and coffee for each of my 5 nights. Ideally averaging under $100 a night. Is this even possible?
   1. Specific recommendations are helpful;
   2. If you have experience with one of the outfitters / package companies that offer a flat rate for a full plan and lodging arrangements (plus add-ons, etc.), I'd like to know if you found it worthwhile. It might blow my budget, but if it removes all the planning and logistics and gets me better lodging than I'd be able to arrange on my own, then it could be worthwhile.
3. How harshly would I be judged if I cut over to Virginia at Point of Rocks so I can take the paved W&OD home instead of the C&O? If there's rough weather, my booty would probably appreciate flat-paved over rocky-muddy, but will my ego regret it forever?? (Considering I can ride the C&O from DC to Harpers Ferry whenever I want anyway...)