Folks in my family came to Oregon in, on and around covered wagons, part of the great migration that brought about 400,000 people across the Great Plains and Rocky Mountains to occupy the land that they thought was available up and down the West Coast. (There were people living here already, it turned out.) My indirect ancestor on my mom's side (something like great-great-uncle, I believe) was Ezra Meeker.
Meeker came out via covered wagon, and then after a very busy life of business, planting hops, founding a town and going to the Klondike in gold rush days, noticed that now, in the early 20th century, people were forgetting about the Oregon Trail. He opted to do something about that. Ezra mounted an expedition - at age 71 - to travel the trail backwards, by ox-drawn wagon, to raise awareness for the trail's preservation. He succeeded, and kept going, eventually reaching New York and Washington DC, meeting with President Teddy Roosevelt. He eventually crossed the country by wagon, train, automobile and airplane and managed to place (or have placed) hundreds of Oregon Trail markers. You can read more about him and his trips in his journals, available in physical form or online.