The first issue appeared in summer 1998 and featured work by R.T. Smith, David Rothenberg, Rick Cole, James Howard Kunstler, Sherry Saye, and others.

[1] Contributors and interview subjects since then include Alison Hawthorne Deming, David Quammen, Lauret Savoy, Terry Tempest Williams, Joy Harjo, Sandra Steingraber, Scott Russell Sanders, Kathryn Miles, Gary Snyder, Wendell Berry, Andrés Duany, and many others.

[citation needed] In March 2009 Web del Sol called Terrain.org a "Top 50 Literary Magazine and Metazine.

[9] The online journal also has a partnership with the journal/book series Terra Nova: Nature & Culture, published by MIT Press.

For example, Terrain.org's 24th issue, with the theme of "Borders & Bridges,"[10] was launched with a reading featuring Rothenberg, Christopher Cokinos, Pamela Uschuk, and Deborah Fries in September 2009.