For a view of the Medieval town of Assisi (birthplace of Saint Francis of Assisi), hike up to Rocca Maggiore.
The old castle, which dates back to 1174 or earlier. You can go inside and climb the tower to the top, but if you're on short on time like I was, believe me: the vista from around Rocca Maggiore will enchant you anyway. The Basilica of Saint Francis, his tomb, and the Spoleto valley are all visible.
You almost feel like you can imitate Assisi and give up your goods. Who needs them with a landscape this glorious?