[6] In 1684, Gysbert uyt den Bogaert purchased about 460 acres (190 ha) of land from Native Americans, an area at the mouth of Catskill Creek that was bounded on the east by the Hudson River.

The land was further subdivided during the Revolutionary War, but the development of the area (including the foundations of the town of Catskill) only began in the mid-1790s when growth is described in historical sources as "very rapid.

[7]: 6  After his death and the return of his son Thomas T. Thomson from South America in 1815, the doctor and his family purchased and leased neighboring lots until their property encompassed 155 acres (0.63 km2) at its apex.

"[7]: 15  Looking to secure a more permanent residence in the Catskill area while maintaining a studio in New York City, Cole rented space from the Thomson family to live and paint.

Cedar Grove continues to offer views of the Catskill mountains, and Cole expressed his feelings for the site and its proximity to the wilderness in poetry and letters.

Whene'er I think to part From thine all peaceful shades my aching heart Is like to his who leaves some blessed shore A weeping exile ne'er to see it more…[7]: 16 Cole purchased two and a half acres of land outright from John A. Thomson, intending to construct a separate house for his wife and himself, but never did so.

Following Cole's death, a number of artists traveled to visit Cedar Grove, with some renting his studio and making paintings and sketches of the houses and grounds.

Cole's privileged position in American art during the mid-19th century ensured constant interest in his place of work by the artistic community until many years after his death.

The size of the property gradually diminished due to a combination of public works (including a road and reservoir) and sales to help the family's financial situation.