So this weekend I got to be in a wedding hosted at a beautiful historical estate in South Eastern PA. There were lots of trails around and me and some friends walked around, we came upon an old stone with something etched into it but it was to weathered to read. I asked someone who worked at the estate and they said that, that particular stone and others like it had been used to line the road to Philadelphia and tell travelers how far they were from the city. So my question is other then stone markers, what kind of things would travelers expect to see during colonial times, other then natural landmarks that would help them find their way? And was there any sort of formal system to place objects to help direct travelers?
Colonial roads were generally terrible. If you look at a map of the colonies, a narrow band strung out along the Atlantic shore, you can understand why water transport whenever possible was preferred. Plantation houses on the Chesapeake tended to face the river landing, not a road.
I would expect a road near Philadelphia to be one of the better ones, as of course it was a very important city. The Great Wagon Road , going west from there to York and Lancaster , did have markers indicating miles from Philadelphia by around 1740. But travelers could expect tree-stumps and washouts and few signs on most roads, as there really was no systematic repair or management of them. In 1786 an Italian traveler on the Great Road between Staunton and Winchester Virginia ( now Rt 11) battered his carriage so badly that he abandoned it in pieces at the first blacksmith's shop he came to and proceeded on horseback. In 1785 Virginia created a turnpike ( I think the first in the country) from the heavily-traveled road over the Blue Ridge that connected Alexandria with the Shenandoah Valley , and the Alexandria Road used that money to pay for repairs and construction. Other turnpikes were soon built in the other states.
In 1811, Congress would appropriate funds for the National Road, which would eventually connect Baltimore to Vandalia, Il. But even then, though the leg between Baltimore and Brownsville PA was heavily used ( in the 1830's-40's it was the main route from the mid-Atlantic to the Ohio river and the steamboats that were the main transportation to the Southern states) the road was often neglected and notoriously challenging.
Warren Hofstra, Karl Raitz, eds: The Great Valley Road of Virginia
Karl Raitz, et al: The National Road
Charles Landis: The King's Highway
While there are generally good reasons to avoid Wikipedia, the present article there on the Great Wagon Road ( which might be the road you saw) shows some care: it is actually pretty detailed, and has a lot of good sources and useful links. https://en.wikipedia.org/wiki/Great_Wagon_Road#Philadelphia_to_York,_Pennsylvania