This area shares its early history with its neighboring communities, Abell and Better Waverly. Harwood was originally part of the second “Huntingdon” tract, surveyed for John and Ashsah (Ridgely) Carnan in 1757. In the early 1840s, the Philadelphia, Washington, and Baltimore Railroad began to run a single tract east and west through the neighborhood. Although the train had little impact at first, by 1878, traffic on the now double track of the Baltimore and Ohio Railroad had increased to sixty trains per day. In the 1870s, the Harwood area was known as Oxford, and was a companion to the other nearby small villages of Friendship and Homestead. Major settlement at this time existed east of York Road, where today’s 27th Street was known as Oxford Street, 28th Street as Brady Street, and Mathews Street as Frisby Street. Considerable brick and frame construction had occurred near the intersection of 25th and Barclay streets, and Sumwalt Lane.

Harwood played an important role in Baltimore’s baseball history, as teams, leagues and playing sites hop scotched all over the City. The first field, named Oriole Park, was located in the vicinity of today’s 29th Street and Greenmount Avenue. In 1891, this field was abandoned because of its distance from the City. For the next 25 years, Union Park at 25th and Barclay streets was the predominate seat of baseball in Baltimore. In 1901, however, an American League Park was built on the site of the first Oriole Park. Later, in 1914, Terrapin Pak was built north of 29th Street and was bounded by Vineyard Lane, 30th Street, and the backs of the houses built along the west side of Greenmount Avenue. The Orioles of the Federal League played here for a few years until the league was disbanded. In 1916, the site was renamed Oriole Park, and became synonymous with baseball in Baltimore until it inadvertently burned down in 1944. This land stood vacant until the Barclay School was built to the west in 1959.