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Highland is an unincorporated census-designated place (CDP) in southern Howard County, Maryland, centered on the rural crossroads of Highland Road, Maryland Route 216, and Maryland Route 108.

The 2020 census counted 1,133 residents in Highland, up 9.6% from 1,034 in 2010.

Highland had 374 housing units in the 2020 census, 362 of them occupied, and its median age was 46.3 years.

The community's historic district sits within the 418-acre 'Hickory Ridge' land grant, where the White Hall estate — home over time to the Ridgely, Hopkins, and Disney families — dates to 1749.

Richard Wells founded Well's Tavern at the crossroads in 1759, and the tavern later became a meeting place for Northern sympathizers during the Civil War.

The crossroads is believed to have hosted meetings of anti-British colonists who influenced the 1774 burning of the brig Peggy Stewart in Annapolis.

In 1842 Joshua B. Disney opened a wheelwright shop at the crossroads, the same year William Wall opened a general store and post office under the short-lived name Walls Crossroads.

The post office was renamed Highland on December 2, 1878, a name reflecting the community's elevation.

Highland never had direct rail service; its link to the Baltimore and Ohio Railroad was nine miles away at Laurel, reached by today's Maryland Route 216.

In 1904 Highland was described as the 'literary center of the county,' and the Virginia Hardy Boarding School operated there around the turn of the twentieth century.