Last spring I rode the Natchez Trace Parkway from Tupelo to Natchez, and the Mississippi River Trail up to Vicksburg over 10 days or so. There are some gentle hills, and near the river there are some bluffs and steep climbs. It's hillier up towards Vicksburg. I was there during the Spring Pilgrimmage but didn't see any indication of Belles on Bikes. Maybe I just missed it. Natchez is a beautiful place. The Parkway is nice to ride in the spring before the RVs come out, but I found the MRT to be more interesting.