Highland is an unincorporated community and census-designated place in Howard County, Maryland, United States. The community 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. 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. In 2014, the Crossroads were placed on the Preserve Howard top ten most endangered list due to current DPZ plans. They are marked by four signs.
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. 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. The Virginia Hardy Boarding School provided classes for students during the turn of the century.