Highland is located in southern Howard County 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 various shops including some that share in the town history. Clarksville is 2 miles to the north on MD 108, Laurel is 9 miles to the southeast on MD 216, and Olney is 7 miles to the west on MD 108. The center of Columbia is 8 miles to the northeast.
The majority of the downtown Highland district is situated within the 418-acre land grant named “Hickory Ridge”. 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.
These charts show statistics in Highland, MD for the following: Median Sale Price, Active Listings, Days on Market, Months of Supply. Each chart shows Detached and Attached housing types.