Penelope Rosemont (born 1942 in Chicago, Illinois) is a visual artist, writer, publisher, and social activist who attended Lake Forest College.

[1] She was in 1964-1966 a member of the Industrial Workers of the World (IWW), commonly known as the Wobblies, and was part of the national staff of Students for a Democratic Society (SDS) in 1967-68.

[2] In 1986, Penelope Rosemont's painting the "Marriage of Heaven and Hell" was included in the Venice Biennale, selected by Arturo Schwartz to be in the Art and Alchemy section.

There, Lewis wrote: "There was also a group of young people in Chicago in the late 1960s who made a connection between Surrealism and the old IWW, The Rebel Worker in which translations of Surrealist writing appeared .

"[7] In his book Freedom Dreams, published in Boston, 2002, Robin D. G. Kelley writes: “my search for an even more elaborate, complete dream of freedom...thanks to the many wonderful chance encounters with Franklin Rosemont, Penelope Rosemont, Ted Joans, Laura Corsiglia and Jayne Cortez, I discovered surrealism...right under my nose, so to speak, buried in the rich black soil of Afrodiasporic culture.” p. 4.

It features Meret Oppenheim, Mary Low, Leonora Carrington, Nancy Cunard, Frida Kahlo, Dorothea Tanning, Elisa Breton, Kay Sage, Jayne Cortez, Rikki Ducornet and over one hundred more.

In 1983, she and Franklin Rosemont became directors of Charles H. Kerr & Company, a publisher of books on history and Chicago history [9] The Alternatives in Publication Task Force of the Social Responsibilities Round Table of the American Library Association awards the Jackie Eubanks Memorial Award, which "recognizes outstanding achievement in promoting the acquisition and use of alternative materials in libraries.".

With Franklin Rosemont she compiled a collection of pamphlets, wall posters, and periodicals focusing on the IWW acquired by the Newberry Library in 2008[12] Her book Armitage Avenue Transcendentalists details stories in the lives of a number of activists, including famous Chicagoan Studs Terkel.