Maher was born in Amarillo, Texas, where his father was stationed in the Air Force. Shortly afterwards the family moved to Lowell, Massachusetts, where Maher remained through childhood. Upon graduating from Dracut High School, he joined the United States Navy where he served in the Persian Gulf aboard the USS Ramsey. Upon discharge, Maher returned to Lowell. He attended Middlesex Community College and the University of Massachusetts Lowell, where he obtained an undergraduate degree in American studies. He later completed a master's degree in Education with a concentration in English.

From 2004 through the present, Maher authored and edited five books for publication. Maher is also rewriting his book on the real-life adventures of Jack Kerouac's On the Road. Ongoing projects are his transcriptions and annotations of the unpublished Extracts Related to the Indians by Henry David Thoreau, and Kalendar (working title) a film project based on Thoreau's natural history writings.[