The road generated much controversy when it was first proposed, as the Tea Partiers of the day did not believe that the Federal government should do things like build roads. Thomas Jefferson's push for an "Act to Regulate the Laying Out and Making a Road From Cumberland, in the State Of Maryland, to the State of Ohio" was successful, and 200 years later we have an entire Interstate Highway System—for better or worse.
This road has it's own web site, The Cumberland Road Project, with a complete gallery of photographs. Of course none of the photographs go back to 1811, but they are still interesting. Here is one of the photographs of the Toll House west of Cumberland. I am not sure what it is about the photo, but the people in it look amazingly small to me. Also, I don't think the original travelers rode a trolley.
The Cumberland Road Project
Photo Gallery
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