The founding meeting of what was then simply known as the "Transportation Lawyers Association" took place on Saturday December 3, 1977 in Toronto.

The first annual meeting of the Association took place on December 1 and 2, 1978 in Montreal. Up until the Montreal meeting, the organisation was run by a steering committee chaired by Doug MacLeod. Operated under the name of "Canadian Transportation Lawyers Association". At the Montreal meeting, a constitution was proposed and adopted, and the Association's name was adopted as "The Canadian Highway Transport Lawyers' Association" and Doug MacLeod was elected as the first President. The second annual meeting of The CHTLA was held in Toronto on November 29-December 1, 1979.

Past presidents

* C. Douglas MacLeod 1978-1979

*  Gilles J. Belanger 1979-1980

*  Joseph W. Kanuka 1980-1981

Peter G. Green 1981-1982

* Hugh G. Morris 1982-1983

Jacques Dufresne 1983-1984

Dean Saul 1984-1985

*  Roderick W. Macdonald 1985-1986

François Rouette 1986-1987

*  Thomas J. Duckworth 1987-1988

David W. Gruchy 1988-1989

Robert B. Warren 1989-1990

Jocelyn H. LeClerc 1990-1991

Robert T. Gabor 1991-1992

Michael J. O’Hara 1992-1993

Catherine A. Pawluch 1993-1994

David F. Blair 1994-1995

Mel F. Belich 1995-1996

R. Wayne Myles 1996-1997

Douglas C. McTavish 1997-1998

Jean G. Bertrand 1998-1999

Tobin S. Robbins 1999-2000

Steven G. Zatzman 2000-2001

Joanne C. Coldwell 2001-2002

Louise Baillargeon 2002-2003

Alex G. MacWilliam 2003-2004

Joan F. Myles 2004-2005

Rui M. Fernandes 2005-2006

Jean E. Clerk 2006-2007

Geoffrey L. Spencer 2007-2008

Louis Amato-Gauci 2008-2009

Douglas I. Evanchuk 2009-2010

Daniel P. Ryall 2010-2011

Kim E. Stoll 2011-2012

Stéphane Lamarre 2012-2013

Marc D. Isaacs 2013-2014

Roger Watts 2014-2015

Sanj Sood 2015-2016

*  Myer Rabin 2016-2017

*  Deceased