He attended Harvard from 1816 and developed an interest in natural history under the guidance of his tutor, William Dandridge Peck.

[1] Oakes was among the first travelers on a path to the summit of Mount Washington, New Hampshire, that had been constructed in 1821 by the pioneering Ethan Crawford.

[3] Oakes eventually gave up law to pursue full-time his interest in natural history.

He was asked to contribute a description of White Mountains flora to a geological survey report in 1842 and thereafter spent much time on the project.

The writings of Oakes, together with work by Asa Gray, were a significant source for a report produced by George Barrell Emerson in 1846 concerning the trees and shrubs of Massachusetts.