Barry received a Bachelor of Environmental Studies in 1974 and Certificate of Public Sector Management in 1997 from the University of Manitoba. He enrolled in the Master of Landscape Architecture program at the University of California - Berkeley in 1976, working as a Teaching Assistant in Intensive Design and Urban Design studios. He met his future wife Bette-Lou while working on his master’s practicum for the Town of Annapolis Royal, and under the conditions of a practical training visa from UC Berkeley, they lived for a year in Vermont while Barry apprenticed under Dan Kiley.
At the City of Saskatoon Barry was involved in long range planning, subdivision design and urban design from 1983 until 1987. At the City of Winnipeg between 1987 and 1999 he was Historic Projects Coordinator and Senior Urban Designer, serving as project manager of the “Exchange District Streetscape Program”, and manager of the Winnipeg Core Area Initiatives’ “Exchange District Redevelopment” and “Riverbank Enhancement” programs. Between 1999 and 2007 Barry worked in the private sector, establishing a new Planning / Landscape Architecture component in Smith-Carter’s multi-disciplinary A&E design firm. And since February of 2007, Barry has worked on Halifax Regional Municipality’s Streetscape Program.
Barry was an Adjunct Professor at the University of Manitoba’s Department of Landscape Architecture for fourteen years, mentoring students interested in urban design. From 2004 until 2007 he was MALA’s representative on the City of Winnipeg’s Downtown Design Review Committee, was President of MALA, and Chair of the Governance Committee of the CSLA.