People and history are shaped by place. To truly understand your ancestors, it helps to walk their land, see the towns they knew, and forge deeper connections by visiting the sites of their life. These heritage quests are more productive and fulfilling with preparation beforehand, through city directories and local historical societies, and online tools such as search engines, Google Maps, Findagrave, Facebook, and Pinterest. By exploring several personal case studies (in Nebraska, Pennsylvania, Denmark, Wales, and England), I will share helpful procedures and ideas: what is there to see, which technological resources will aid you, and how will a trip bring meaningful insights to your genealogical research? Walk in ancestral footsteps, broaden your horizons, and get in touch with the dirt your roots came from!