After their father died of tuberculosis, their mother moved with the two boys to live with their grandmother in the Fletcher homestead, a strict Puritan home, in Norridgewock, Maine, where Dole grew up.

Sophie May wrote her Prudy Books in Norridgewock, and they may be an indication of the sort of life Nathan Dole and his brother lived there.

The same Boston Evening Transcript article said that Nathan was an omnivorous reader, who soon taught himself to read in French, German, Greek and Latin.

In 1928, when he was seventy-six, Dole and his wife moved to New York City to be near their daughter and grandchildren and lived in Riverdale-on-Hudson.

Dole knew the literary giants Ralph Waldo Emerson, Henry Wadsworth Longfellow (who was his father's instructor in Bowdoin College), Oliver Wendell Holmes Sr., William Cullen Bryant, James Russell Lowell, Charles Anderson Dana, Walt Whitman, William Dean Howells, John Greenleaf Whittier, Thomas Wentworth Higginson, Edward Everett Hale, Julia Ward Howe, Louise Chandler Moulton, Byrd Spilman Dewey and many others.