Shepard's first creative writing teacher was David Huddle, poet and short story writer at the University of Vermont. Shepard studied with Bill Tremblay for his Master's work at Colorado State University and with Stanley Plumly, Wayne Dodd, and Paul Nelson for his doctoral work at Ohio University.

Other influences on Shepard's poetry include his many years playing piano and guitar; his love of jazz (bebop and post?bebop), soul, and classical music; world?wide treks in the moun­tains, from China to New Zealand to Norway to Switzerland to the American Rockies; con­stant forays into the natural world; amateur birding; summers along the Maine coast; long residence in northern New England; year-long sojourns in Shanghai, China (1991), the Marquesas Islands in the South Pacific (1993), and France (2003).

His marriage to Kate Riley, linguistic anthropologist and fiction writer, introduced Shepard to the South Pacific, French language and French colonial culture. He accompanied Riley to the Marquesas Islands, where she conducted her fieldwork on language and culture, and eventually Shepard wrote the Marquesan poems that appear in his second book, I'm Here Because I Lost My Way.

The birth of his only daughter, Anna Riley?Shepard (b. 1995), has also deeply affected his work. A section of poems called “Birth Announcements” appears in Shepard's third book, This Far from the Source.

Scavenging the Country for a Heartbeat (First Book Award, Mid-List Press, 1993)

I’m Here Because I Lost My Way (Mid-List, 1998)

This Far from the Source (Mid-List, 2006).