Hi, I asked this question of a couple of Bike Rental shops and they told be Brewster. Lots of deep shaded paved paths and a few cute towns too. Don’t think you could go wrong in any section. Would love to ride the whole trail some day.

We picked it up eastham. Just look on a map. It's pretty clear

Yes, there are several stops with restrooms.

We rented from Idle Times. Worked very well. Their rates were lower than the places in Chatham, at least for road bikes, and they had a great selection. We were able to rent from one location and return to another. Bikes came with tire irons and a spare tube which my son needed to use.

I rented from them for $95 for a week. I think it was $65 for 3 days, not sure in daily rate.

No idea,sorry. But please write to any bike renting company in dennis or yarmouth and they will know.

One way and about to get longer

Hi, I'm not sure about this. You would have to call bike shops and find out if they have multiple locations. I rented at a shop in Wellsfleet, Little Capistrano, and biked the trail 11 miles in to Brewster and then 11 miles back to return the bike to the same shop (i was able to return the bike after they closed). If you can't find a shop that allows pick up in one location and return to another, I suggest you figure what part of the trail you want to bike and rent nearby and plan the trip accordingly. Orleans is pretty central and there is a bike shop there. You could then go either direction and easily get back to Orleans.