[5] Kent's early paintings of Mount Monadnock and New Hampshire were first shown at the Society of American Artists in New York in 1904, when Dublin Pond was purchased by Smith College.

A transcendentalist and mystic in the tradition of Thoreau and Emerson, whose works he read, Kent found inspiration in the austerity and stark beauty of wilderness.

After Monhegan, he lived for extended periods of time in Winona, Minnesota (1912–1913), Newfoundland (1914–15), Alaska (1918–19), Vermont (1919–1925), Tierra del Fuego (1922–23), Ireland (1926), and Greenland (1929; 1931–32; 1934–35).

His series of land and seascapes from these often forbidding locales convey the Symbolist spirit evoking the mysteries and cosmic wonders of the natural world.

Approached in 1926 by publisher R. R. Donnelley to produce an illustrated edition of Richard Henry Dana Jr.'s Two Years Before the Mast, Kent suggested Moby-Dick instead.

As the pen-and-ink draftsman "Hogarth Jr.," Kent created dozens of whimsical and smartly irreverent drawings published by Vanity Fair, New York Tribune, Harper's Weekly, and the original Life.

He also brought his Hogarth Jr., style to a series of richly colored reverse paintings on glass that he completed in 1918 and exhibited at Wanamaker's Department Store.

In Rockwell Kent: The Mythic and the Modern, Jake Milgram Wien devotes an entire chapter to Hogarth Jr. and reproduces several of the ink drawings and reverse paintings on glass.

The work of transferring and painting the designs on the 6,400-square-foot (590 m2) span was done by Kent's collaborator Jo Mielziner (1901–1976) and a crew of stage set painters from New York City.

Ostensibly staying away from the state of Massachusetts to protest the Sacco and Vanzetti executions of 1927, Kent did in fact venture to Dennis in June 1930 to spend three days on the scaffolding, making suggestions and corrections.

After meeting Danish Arctic explorers Peter Freuchen and Knud Rasmussen on this trip, Kent determined to return to Greenland to paint and write.

He spent two years (1931–32 and 1934–35) above the Arctic Circle in a tiny fishing settlement called Igdlorssuit (or Illorsuit), where he conceived some of the largest and most celebrated paintings of his career.

Although he came from a relatively privileged background, Kent formed radical political views early in life, joining the Socialist Party of America in 1904.

[19] In the changing postwar context, Kent advocated nuclear disarmament and continued friendship with America's wartime ally, the Soviet Union.

[23] Meanwhile, Kent also came under attack as an officer of the International Workers Order, a mutual benefit and cultural society supported by leftists and immigrants.

In the preface to the second Russian edition of his book "Salamina", Kent wrote: "Recently… I've met two talented young artists from Kyiv Ada Rybachuk and Volodymyr Melnychenko.

"[26] When Kent died of a heart attack in 1971, the New York Times published an extensive front-page obituary that commenced: "At various (and frequently simultaneous) periods of his long life the protean Rockwell Kent was an architect, painter, illustrator, lithographer, xylographer, cartoonist, advertising artist, carpenter, dairy farmer, explorer, trade union leader and political controversialist.

2018 through 2020 marked the 100th anniversary of Kent's Alaskan painting expedition, his stay on Fox Island, and the publication of Wilderness: A Journal of Quiet Adventure in Alaska.

[29] One of Kent's exemplary pen-and-ink drawings from Moby Dick appears on a U.S. postage stamp issued as part of the 2001 commemorative panel celebrating American Illustration, with other artistic examples by Maxfield Parrish, Frederic Remington, and Norman Rockwell.

Kent's work also figures in Steve Martin's 2010 novel An Object of Beauty and is the subject of a chapter in Douglas Brinkley's 2011 history The Quiet World: Saving Alaska's Wilderness Kingdom: 1879–1960.