Druid Heights boundaries extend clockwise from North and Madison Avenues along Madison, Presstman, McCulloh, Laurens, Division, Bloom, Pennsylvania, and North. Before development, southern blocks formed part of Hatsworth, northern blocks a section of Hap Hazard, eighteenth- and nineteenth-century property of the Lawson family thatextended to Druid Hill Park. Alexander Lawson Sr., Baltimore county iron master and one-time manager of the Nottingham Iron Works, acquired it in 1741, His Oxford educated son, Lawson Jr., once served as clerk of Baltimore County. A stream, Spicer's Run, once ran between Druid Hill and Division to Laurens and thence eastward.

Distant from markets, schools, and churches in the era of the horse-drawn trolley, Druid Heights developed with the northern blocks of Upton but with fewer public and private institutions. Residential development extended gradually across twenty-eight blocks from 1870 to 1900. A city railway company kept stables and passenger car repair shops along the city boundary at Cumberland from the 1870s to World War I. Two chapels, St. Bartholomew's Episcopal. and Ames Methodist Episcopal on Division Street between Gold and Baker Streets, served rural congregations, the latter Baltimore County African Americans. In the 1880s developers built smaller two-story ltalianate houses along Division and Etting and cast of Pennsylvania north of Bloom, in the 1890s, ornate, grander houses in northeastern blocks were erected as housing went up in Madison North. When trolley repair shops were torn down in the 1920s, modern, shallow-depth row housing, with front porches, was introduced along Cumberland. Two commercial stretches of shops and stores, eight blocks along Pennsylvania and North Avenues, have capped Druid Heights at the northwest edge ever since.

Heights blocks were first populated by affluent whites, but electrified trolleys encouraged both out-migration and the extension of Upton as a largely but not exclusively African-American residential section. Shopkeepers' families, many second-generation Greeks, Russian Jews, and Chinese. moved in atop streetcorner laundry and grocery stores, and on Pennsylvania Avenue. But with no large markets or schools and few churches in the neighborhood, and with a North Avenue commercial district which catered to a white clientele, residents relied heavily on trolleys and patronized Upton and downtown institutions. Three lines ran north and south, an all-night line east and west, with every neighborhood block within two blocks of a car line. Tenants replaced homeowners in most residential property between 1960 and 1980.

These blocks contain two old churches and one new branch library and post office. St. Katherine's of Alexandria Episcopal, organized as a "colored" mission of Mount Calvary, moved into a stone, brick, and wooden chapel at Division and Presstman in 1911, a building which had been built for the white congregation of St. George Episcopal in 1882. The congregation was accorded parish status in 1975. Its rectorandcongregationspearheaded formation of the Druid Heights Community Association which met at the Church in the mid-1970s. Madison Avenue Presbyterian, the oldest black Presbyterian Church in the city, relocated in an edifice built by the Evangelical Lutheran Church of the Incarnation in 1927. Begun by blacks who refused segregated worship in the congregation of First Presbyterian, and headed by clergymen active in freedmen's aid work, the church was formed on Madison Street near Park about 1848.

Enoch Pratt's Pennsylvania Avenue branch, one of the city's largest, opened in 1953 and was designed by architects Smith and Veale. It featured innovations in library design. Glass panels made up the two-story wall on the entry sides, thereby maximizing natural light and making books and readers visible from the street in order to lure patrons. Fire Engine House #25 was opened as a suburban station for horse-drawn vehicles and equipment on Druid Hill next to North in 1903.