Half way into the walk you will walk past Loventor Manor. This is an ancient settlement location, with its name coming from Leofwynne, the Saxon founder. The current house is late 16th century, with extra wings added over the years.
A little further on you will see Berry Pomeroy Castle through the trees. The de la Pomeroys were among the first Norman families to claim a barony in England in the 11th century. There is a public footpath which leads to the castle through the woods if you want to make a visit (there are limited seasonal facilities at the castle).
When you reach Totnes, you will enter a part of town called Bridgetown. It was first developed in medieval times by the de la Pomeroy family. The bridge was built in 1828 by Charles Fowler, a Devon architect who was responsible for Covent Garden in London.