I never asked what Washington would do, I asked if he was required to have a license to ride his horse from point A to point B.
We have what were called "Rolling Roads" around here. Those were roads set aside for the purpose of moving tobacco from plantations to ports to be loaded for shipment to Europe.
Since no one had any money back in colonial times, the planters would "donate" right of way for construction of the "rolling road". Others would donate hogsheads of tobacco to the county to improve and clear the roadway.
Years back the Commonwealth of Virginia proposed cutting off the historic residual (which made up my housing development) from its rights to access a "rolling road". They intended to build a brand new super highway between my house and the "rolling road".
We went to a public hearing where I claimed my right of access. The State and county figured it was easier to buy me off than challenge my right of access ~ which is how we got a stoplight system at the entrance to our development on a different main thoroughfare.
The colonial owner of this site at the time the "rolling road" was built was a Mr. Fitzhugh, a notorious Tory who never even visited America. His property was seized by the Commonwealth during the Revolution, but at the conclusion of the War and the signing of the Treaty of Paris, the "rights" pertaining to his land and his usages (albeit under new owners) were re-estblished.
George Washington would have needed the explicit permission of Mr. Fitzhugh (in London) to travel from Cherry Valley in the North to Mount Vernon in the South but for the "rolling road" I mentioned. That he, he would have needed "license". Fortunately for me Fitzhugh managed to get the "rolling road" built on his land rather than his neighbors, so he didn't need to pay for maintenance ~ at the same time, every part of the area retained a right of access to the "rolling road" for time ever after!