In early 1900s Oklahoma, the Abernathy brothers decided they wanted to go see the new governor’s mansion in Santa Fe, NM. 1,300 miles away. On horseback. Alone. They had to ask their dad for permission first - since they were nine and five years old. He said go for it.
Sources
https://www.washingtonpost.com/history/2019/10/19/ultimate-free-range-kids-two-boys-rode-horses-new-york-oklahoma/ By Eliza McGraw
https://www.405magazine.com/the-astounding-adventures-of-the-abernathy-boys/ by M.J. Alexander