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Hilles lived for many years in Calgary, Alberta and was very active in the writing community there. For ten years he acted as the managing editor of Dandelion, the oldest surviving literary magazine in Alberta. He developed the magazine from a small pamphlet to one of the most respected literary magazines in Canada. During that time he also organized many successful readings featuring writers from across the country. In 2001, he moved to British Columbia and has been very active in the literary community there, especially on Salt Spring Island where he now lives. He among other writers helped set up a scholarship for beginning writers on Salt Spring and also organized a new reading series on the island.
He served on the executive of the League of Canadian Poets for five years and in 1996 was sent by the League of Canadian Poets and the Department of Foreign Affairs to represent Canada at an International Poetry Festival in Japan. Hilles won the 1994 Governor General's Award for Poetry for Cantos From A Small Room (1993). In the same year, his first novel, Raising of Voices (1993), won the Writers Guild of Alberta George Bugnet Award for best novel. He has published thirteen books of poetry and fours books of prose.
Wrapped Within Again, New and Selected Poems was published in the fall of 2003 and won the Stephan Stephansson Award. His second novel, A Gradual Ruin, was published by Doubleday Canada in 2004 and is now available in paperback. His books have also been shortlisted for the Milton Acorn People’s Poetry Prize, the W.O. Mitchell/City of Calgary Prize, the Stephan Stephansson Award, and the Howard O’Hagan Award.
- Look the Lovely Animal Speaks (1980), ISBN 0-88801-053-2
- The Surprise Element (1982)
- An Angel in the Works (1983), ISBN 0-88982-052-X
- Outlasting the Landscape (1989), ISBN 0-920633-61-7
- Finding the Lights on (1991), ISBN 0-919897-27-4
- A Breath at a Time (1992), ISBN 0-88982-110-0
- Raising of Voices (1993), ISBN 0-88753-272-1
- Cantos from a Small Room (1993), ISBN 0-919897-37-1 – winner of the 1994 Governor General's Award for Poetry
- Near Morning (1995), ISBN 0-88753-271-3
- Kissing the Smoke (1996), ISBN 0-88753-283-7
- Nothing Vanishes (1996), ISBN 0-919897-52-5
- Breathing Distance: A Book of Odes (1997), ISBN 0-88753-297-7
- Somewhere Between Obstacles and Pleasure (1999), ISBN 0-88753-327-2
- Higher Ground (2001), ISBN 1-895836-80-8
- Wrapped Within Again: New and Selected (2003), ISBN 0-88753-384-1
- A Gradual Ruin: A Novel (2004), ISBN 0-385-65961-X
- Calling the Wild (2005), ISBN 0-88753-411-2
- Slow Ascent (2006), ISBN 0-88753-428-7
- Partake (2010), ISBN 097808875343