Beginning at the rose garden and ending with the circular Four Seasons Overlook, this secluded path is flanked by boxwood, rhododendrons, and azaleas. The overlook is shaded by magnolia, crape myrtle, white pine, and American Holly trees.

A secret committee, including Frances Rosso, Lady Constance Lewis, and Sadie Pratt, devised the Friendship Walk as a way to celebrate Marjorie Post’s seventieth birthday and honor her remarkable philanthropic contributions. With the help of her chief gardener and landscape architect Perry Wheeler, and with contributions by 181 friends, in November of 1957 the astonished Post was led to a pair of gates off the rose garden. There lay a marble plaque set into the ground that read, “Friendship Walk – Hillwood – Dedicated by her friends as a tribute to Marjorie Merriweather Post for her generous nature, love of beauty, and devotion to human needs.” Post regularly showed the Friendship Walk to visitors and often slipped off to the path for solitary contemplation.