The roots of Highland, Maryland’s history run as deep as the rich soil which nurtured this community from its earliest days as a simple farming town at the crossroads on the carriageway from Montgomery County to Annapolis.

Rannie Bros Truck in Highland

The Greater Highland Crossroads Association is devoted to preserving and nurturing this legacy. In this section of the website, we share with you collected lore. Some of it is anecdotal, based on recollections of long-time residents. All of it is interesting reading for those hungry for insight into what makes Highland so worthy of protection and respect.

A History of Highland

Highland Bank
Kendall Gambrill grew up in Highland in the 1950s and ‘60s. He loved nothing more than to walk the country roads of the area, studying the original homes and chatting with residents. He steeped himself in the history and lore of the environs. This became the basis of the following document which he wrote in 1965 while studying at the University of Maryland.

Read Kendall W. Gambrill’s History of Highland

Additional Highland History Articles

The following collection of articles originally appeared in the Highland Business Directory, published and distributed annually in conjunction with the observance of Highland Day. The pieces were researched and written by members of GHCA. We hope you will enjoy the insight they provide into the fascinating people and past of our beloved crossroads community.

Highland’s Own Iron Man: The Story of Malcolm Disney

Highland's Baseball Team

Download the article (PDF), written by Hilda Mathieu.

Family Farms: The Building Blocks of Highland

Family Farms of Highland

Download the article (PDF), written by Charlotte Williams.

A Salute to Highland Day: Ten Years and Counting

Highland Day Pipers

Download the article (PDF).

Historic Hickory Ridge

Hickory Ridge
Download the article (PDF), written by Charlotte Williams.