I was only able to hike about 2 miles down from Cumberland. The path seems more suited to running and biking. It is pretty. I am far more interested in the kayaking possibilities, but was surprised to see no one on the river and little information available at the outfitter in Cumberland.
Some friends and I actually picked up the canal just over the Ohio line and hiked the towpath all the way to DC. we all had a great time there was times when we would. Along the trail and other times we really had the home to make up for lost time and bad weather. all in all it took us about two weeks plus or minus a few days to make the entire trip and we are planning on doing it again in the near future with our children.
I lived in Cumberland, MD for 2 years. I did several out and backs on the trail, as it this is the starting point. Enjoyed the museum. I biked a few times on it, and sometimes parked closer to some of the more interesting spots, as I got tired of seeing the same 4-5 miles before turning around. On a visit to Harper's Ferry, saw a very cool section. I am interested in running the Ultra Marathon one day.
Technically a mountain bike trail, but fit just as easy for hiking as well. short but many elevation changes as well as different terrains- from mud to very dry. Bring extra water in the summer as it gets very hot in Green Ridge during the June,July,August months. Scenery is fantastic, but no real overlooks (though they are close by). Use this in conjuction with the Will's Mountain Trail to train for distance hiking. Bring tick and insect protection. It is bear and snake country, but also falcon,eagle,deer,and close to good camping and fishing spots. Near the towns of Little Orleans, Flintstone, Hancock, and Cumberland for provisions. Do the hike and reward yourself with the awesome burgers at the diner in Little Orleans.