What is Cumberland? The answer is: a city and a gap
with the same name, both playing important roles in the settling
of the Ohio Valley, but not located together.
There are two Cumberlands of interest as they are both key
points on the major routes from the East to the Ohio
Valley. The two can be confusing because they are
not the same thing and are not located in the same place. The
Cumberland Gap is a natural break in the ridges of the Appalachian
Mountains. Daniel Boon blazed the Wilderness Trail through this
gap in 1775 and linked southwest Virginia with Tennessee and
Kentucky. About one quarter of a million settlers followed him
through this gap. The area of Cumberland Gap is shown on Map
A by the orange transparent mark where Virginia, Tennessee,
and Kentucky all meet (lower left section of map). The Gap itself
is marked by the two black triangles point to point.

This map is Exploration and Settlement
1800-1820 from the U.S. National Atlas, 1970. Settlement has
reached the Mississippi and beyond. Source: This map was downloaded
from the Perry-Castañeda
Library Map Collection of the University of Texas at
Austin.
The city of Cumberland is several hundred miles northeast of
the Cumberland Gap. It is highlighted by the orange transparent
mark in the northwest corner of Maryland (upper center of map).
The town itself is indicated by a small round black dot indicating
a smaller city or town. Located far up the Potomac Valley, it
was the starting point for the National Road which heads west
into Ohio and Indiana. An earlier road led from the port city
of Baltimore to Cumberland. Later, the C&O canal would reach
from Georgetown (Washington, DC) to Cumberland and then no further.
The National Road provided a genuine road by which wagons and
stage coaches could travel west. The famous Conestoga wagon,
associated in our minds today with the trip to California or
Oregon, was used here.