Iconography of gravestones at burying grounds

The earliest gravestones in Boston's burying grounds were simple, roughly hewn "greenstone" markers. Generally, these stones had little or no decorative carving and often had brief inscriptions, which usually gave the name of the person interred and their death date. Inscriptions on these stones have "interruptive punctuation," a carving style characterized by a raised period between each word.

The second type of decorative motif used on Boston's seventeenth-century gravemarkers was the "death's head." A death's head, often with wings or crossed bones, or both, was a stylized skull. Some have speculated that winged skulls were intended to symbolize a combination of physical death and spiritual regeneration. It is important to note that Boston-based Puritans did not advocate using religious symbols, such as cherubs, Christ figures, or crosses in their meetinghouses, on church silver, or on their gravestones. Puritans were adamantly against attributing human form to spiritual beings such as God, angels, or spirits.

By the 1690s, another iconographic motif began to appear on Boston's gravestones. Called a winged cherub or a soul effigy, this motif was characterized by a fleshy face, life-like eyes, and an upwards-turned mouth. Some historians and students of material culture have asserted that the greater use of winged cherubic images, which have been interpreted as a symbol for the soul's flight to heaven, was indicative of changing religious sentiments. This theory asserts that changing religious philosophies led to greater acceptance and more widespread usage of symbols forbidden because they were considered to be "graven images."

After much research, however, historians and statisticians have discovered that as a motif the cherub never truly displaced the death's head. Moreover, this shift from death's head to cherubic imagery did not correspond chronologically with any of the religious movements of the eighteenth century. Both death's head and cherub were widely employed motifs well into the late-eighteenth century, although the death's head appears more often on Boston stones than cherubs.

As political ideologies and philosophies of the new nation began to change, so did attitudes about death and mourning. Neo-classical philosophies and attitudes began to dominate the material cultural evidences of post-Revolutionary society and culture. As notions of classicism in art and architecture began to evolve, American citizens began to look to the buildings of ancient Rome and Greece for models of their houses, public buildings, and even gravestones.

The predominant image used on late eighteenth and early nineteenth-century gravestones was the willow and urn motif. The willow was an ancient mourning symbol. The urn was an Imperial Roman device used to contain ashes. Usage of these motifs was part of a larger trend toward sentimentality in mourning art. Larger, more imposing monuments were also used for memorialization. Obelisks, the Roman order of columns, and pediments were ornamental forms widely used on nineteenth-century markers and monuments.