For about 200 years the road was the principal transportation link between these two cities. The highway carried people, goods and even animals into Washington, D.C. from one direction and out west in the other. Throughout the period numerous 'public houses,' hotels, taverns and other businesses located along this route to serve travelers on it.

Two communities that border Little Bennett - Clarksburg, Hyattstown - are located along this road. Early on in their founding, both towns saw businesses emerge to serve the needs of travelers along the road. Over time, as the area around these two towns was cleared and farmed, merchants gradually began to serve the needs of the growing number of nearby residents, as well. Eventually schools and churches were built and small communities emerged.

While the communities of Clarksburg and Hyattstown have had a big impact on the history of the Little Bennett valley and area, technically they are not a part of the Park of course - though the Park does carry a Clarksburg postal address. However, there are two important historical sites on MD 355, the road connecting Clarksburg and Hyattstown, that are within the physical boundary of the Park.

• Zeigler Log House
• Montgomery Chapel site and cemetery