In the early 20th century its design philosophy changed, when a large mausoleum to local businessman Orator Francis Woodward, who in his last years made a fortune developing Jell-O into a bestselling dessert, was built in the southern section of the cemetery near his factory.

The architect hired by the family to lay out the section was influenced by the City Beautiful movement, giving that area a more orderly cast.

Among the 5,500 dead buried here besides Woodward and his family are many people important to the history of Le Roy, including the daughters of its namesake, the inventor of Jell-O and Sarah Frances Whiting, an astronomer who was also one of the first to experiment with X-rays.

The southern third of the cemetery is generally flat, with axial roads radiating outward from the Woodward mausoleum near the southeast entrance.

The most prominent is the mausoleum of Orator Francis Woodward, the Le Roy resident who built a personal fortune from buying the patent for Jell-O.

It is a small stone Classical Revival structure in the middle of a circle with large planted myrtles at the end of the short drive from the main entrance, serving as its focal point.

John Barlow Olmsted's green serpentine stone, amid a grove of cedars, has a history of the family.

On the south knoll of the cemetery's west side are the graves of the three Bang children, outlined with low marble stones that resemble cribs when seen at a distance.

A fourth Bang child has a nearby grave with a detailed carved cross decorated with ivy and flowers.

Another descendant of a prominent local family, Sheldon Francis Bartow, has a large marble urn embellished with garlands on his stone.

After the construction of the Woodward Mausoleum in the early years of the 20th, subsequent development was influenced by the contemporary City Beautiful movement.

The idea of burying the dead in a large, parklike tract with walking paths and plantings took some time to gain acceptance.

Samuel Cox, first chancellor of Ingham University, suggested the name Machpelah, from Jacob's exhortation at Genesis 49:30: "Bury me with my fathers in the cave in the field of Ephrom the Hittite, the cave in the field of Machpelah ..."[2] The first decedent, twelve-year-old Caro Frances Chamberlin, was buried on the last day of 1858.

Later in that decade the cemetery grew when one of Le Roy's original burying grounds were closed down and the bodies moved.

In this sweet spot, by day and night, while the sun shines and the stars look down, while the rains fall and the dews brighten and the winds blow, nature tenderly and lovingly takes to her breast and keep[s] that which is her own—and I am satisfied.

"The grounds are upon an elevation and are beautifully laid out with an excellent taste displayed in adapting new ideas to the laying out and beautifying of burial plots, which is worthy of imitation."

Two decades later, in 1913, the Le Roy Gazette said: Go where you may and it will be difficult to find a more picturesque spot or one better adapted for a cemetery than that of Machpelah.

Reposing on the east bank of the Oatka, upon slight elevations, it has perfect drainage and with its beautiful trees it presents a handsome picture.

He had made his Jell-O fortune in the last years of his life; his family put it to many philanthropic uses not only in Le Roy but in the greater Rochester area as well.

[2] The roads radiating from the circular drive around the mausoleum impart clean, clear visual lines and symmetry to the landscape, in contrast to the meandering, idiosyncratic rural atmosphere of the older sections.

This reflects the ideals of the contemporary City Beautiful movement, with a preference for symmetry and order in public spaces, particularly since this section directly abuts the factory where Woodward had made his fortune.

Raymond Calkins funded additional work in memory of his wife's family, the Lathrops, giving the chapel its name.

In 2006 the Le Roy Historical Society began putting flags on their graves, a practice the local American Legion post had discontinued in the 1980s due to lack of funds.