Harry R. Pringle

Of Counsel

207.772.1941 Direct
207.772.3627 Fax


84 Marginal Way, Suite 600
Portland, ME 04101-2480


  • Harvard Law School, J.D., cum laude, 1973
  • Princeton University, B.A., magna cum laude, 1968Phi Beta Kappa


  • Maine


  • College of Labor and Employment Lawyers
    Elected Fellow
  • Maine State Bar Association
  • National School Board Association Council of School Board Attorneys
    Board of Directors, 1982 – 1986
  • Maine Council of School Board Attorneys
    Past President


  • Associates of the Osher Map Library
    Founding Director and President
  • Oceanside Conservation Trust of Casco Bay Board of Directors
  • United Way of Greater Portland Board of Directors
    Former Member
  • Portland Public Library Board
    Past President and Member
  • The Children’s Museum of Maine Board
    Past President

Since joining Drummond Woodsum in 1973, Harry Pringle has represented employers on labor and employment issues throughout Maine. Harry has extensive experience in general employment litigation, labor negotiations, arbitrations, National Labor Relations Board and Maine Labor Relations Board proceedings, Title VII litigation, wage and hour matters, and discrimination cases before the courts, the Equal Employment Opportunity Commission and the Maine Human Rights Commission.

In addition to representing private sector employers throughout Maine, Harry also represents school districts and other public sector entities throughout the state. He has handled many of the more significant school law cases decided by the Maine courts over the past 39 years.

Harry has been listed for over 20 years in Best Lawyers in America in the categories Labor and Employment Law and Education Law. He was named Maine's Education Lawyer of the Year for 2011, and has just been selected as Maine's Labor Law-Management Lawyer of the Year for 2014. He is also listed in the current Chambers USA, an independent international guide to the top business lawyers in the U.S. He was selected for inclusion based on his expertise in employment defense matters. In addition, Harry is listed in the Corporate Counsel Edition of Super Lawyers in the category of Employment and Labor Law.

Harry is the editor of Maine School Law (Fourth Edition 2012), an author of Significant Cases in Maine School Law (Second Edition), a co-editor of Maine School Law and Practice for Board Members (Fourth Edition 2012), and has served as the lead instructor for school law courses offered by the University of Southern Maine and the University of New England. Harry has lectured nationally on school and employment matters.

Prior to attending law school, he served with the U.S. Army as a combat infantry sergeant in Vietnam.


  • Education Law Lawyer of the Year, Portland, ME (Awarded by Best Lawyers) (2011)
  • Labor Law - Management Lawyer of the Year, Portland, ME (Awarded by Best Lawyers) (2014)
  • New England Super Lawyers, Employment & Labor, School & Education (2007-2016)
  • Best Lawyers USA
    • Employment Law – Management (2011-2016)
    • Labor Law – Management (2011-2016)
    • Education Law (2008-2016)
  • Martindale Hubbell, AV Preeminent
  • Maine School Superintendents Association (MSSA), Distinguished Service Award (2014)


  • Author, Significant Cases in Maine School Law, 2nd Edition
  • Co-Editor, Maine School Law and Practice for Board Members, 4th Edition (2014)
  • Editor, Maine School Law, 4th Edition (2012)