I've never done it, but I know a lot of people who have, and most years at least some of the route is over roads I'm familiar with. It's supposed to be a super good time.
I'm not sure what the route will be this year. Sometimes they can make it pretty challenging - but 50 miles even of the tougher stuff is plenty manageable.
Let me know if you're going to ride it!
(COP also puts on XOBA, a similar but smaller tour later in the year.)
"I felt [the women's Olympic marathon] was as important as women having the right to vote, because talent, strength, and capability cannot be fully realized if there are no personal rights to allow them to be visible or be deemed significant in the first place." - Kathrine Switzer, Marathon Woman