Jackson is the author of 15 books of poetry, including The Heart as Framed: New and Select Poems, Dispatches, Where The Wind Comes From and Broken Horizons, and 12 books of essays, interviews, translations and anthologies. Other books include: Take Five (Finishing Line, with 4 other poets, 2019), Traversings (Anchor and Plume, 2016) Retrievals (C&R Press, 2014), Out of Place (Ashland, 2014), Resonancia (Barcelona, 2014), a Catalan translation of Resonance [from Ashland, 2010]), Half Lives: Petrarchan Poems (Autumn House, 2004), Unauthorized Autobiography: New and Selected Poems (Ashland, 2003), and Heartwall (UMass, Juniper Prize 2000), as well as four chapbook adaptations from Pavese and other Italian poets, and a chapbook of prose poems, Fifties.

The Heart’s Many Doors is a collection of poems by American poets on the artists Metka Krasovec (Wings press, 2017). He has translated a book of poems by Alexsander Persolja (Potvanje Sonca / Journey of the Sun) (Kulturno Drustvo Vilenica: Slovenia, 2007) as well as Last Voyage, a book of translations of the early-20th-century Italian poet, Giovanni Pascoli, (Red Hen, 2010). In addition, he has edited the selected poems of Slovene poet, Iztok Osijnik. He was awarded the Order of Freedom Medal for literary and humanitarian work during the Balkan wars by the President of Slovenia during his work with the Slovene-based Peace and Sarajevo Committees of PEN International. He has received Guggenheim, Fulbright, NEA, NEH, and two Witter-Bynner fellowships, a Prairie Schooner Reader's Choice Award, and the Crazyhorse Prize, and he is the winner of five Pushcart Prizes, and has appeared in Best American Poems, as well as many other anthologies.

His books and chapbooks have won numerous awards, including the Juniper Prize, Maxine Kumin Award, Cleveland State Poetry Prize, Choice Award, Agee Award, and others. He has given hundreds of readings and lectures in this country and abroad, from Hong Kong to India to Israel and Eastern Europe. He has taught at the Iowa Summer Festival, The Prague Summer Workshops, and regularly at UT-Chattanooga (since 1976), where he directs the Meacham Writers' Conference. He has taught at Vermont College of Fine Arts since 1987, winning teaching awards at both schools.

In 2009 he won the AWP George Garret Award for teaching and writing. His own poems have been translated into nineteen languages, including Worlds Apart: Selected Poems in Slovene. He is the author of Dismantling Time in Contemporary American Poetry (Agee Prize), and Acts of Mind: Interviews with Contemporary American Poets (Choice Award). Originator of Vermont College of Fine Arts’ Slovenia Program, he was a Fulbright Exchange poet to former Yugoslavia, and returns to Europe each year with groups of students. About fifty of his former undergrads have gone on to publish over 120 books, including Paul Guest, Khaled Mattawa, and Cathy Wagner, and many have gone on to editing, such as Rachel Morgan at North American Review. Every undergrad who has applied for a MFA has received a fellowship or assistantship. At Vermont College of Fine Arts he has directed about two dozen theses that have turned into books. He spends his free time in the woods and travelling, having visited most of Europe, from Poland to Portugal, and also Hong Kong, Iceland, Israel, and India, travelling abroad each year.