The community is located at the junction of Highland Road, Maryland Route 216 and Maryland Route 108, and is still heavily influenced by its agrarian history; farms and horse fields are common in the area. The crossroads itself has a small-town feel, with a few shops that share in the rich history.
As a rural crossroads, many of its community members took it upon themselves to maintain the historical sites and feel of the hamlet by founding the Greater Highland Crossroads Association (GHCA) in 2002.
The majority of the downtown Highland district is situated within the 418-acre (169 ha) land grant named “Hickory Ridge”. The Rouse Company borrowed the land grant name for one of its nearby villages of Columbia, built in 1974. The “White Hall” or “Hickory Ridge” slave plantation property was owned by the Ridgley, Hopkins and Disney families. One of the earliest businesses at the crossroads was Well’s tavern, founded by Richard Wells in 1759. This was replaced with a wheelwright’s shop by Joshua B. Disney in 1842. The same year, William Wall opened a general store and post office, giving the crossroads the short-lived name of “Walls Crossroads” before another name change of the post office on December 2, 1878 to “Highland” to reflect the town’s elevation in Howard County. The County Commissioners added Hall Shop Road on the Southern side of the community in 1877. The town did not receive direct rail service, but was only nine miles away from the B&O railroad in Laurel, Maryland using the rolling road now known as Route 216.
Highland played several important roles in U.S. history. The town housed meetings that affected the events of the Boston Tea Party. Well’s Tavern (now the Kitty Bed and Breakfast) was the primary meeting place of a group of Northern sympathizers in the Civil War.
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