In the
1985 Ontario election, she was a candidate for the
Progressive Conservative Party of Ontario in
Waterloo North, and was defeated. She also stood as the candidate for the
Progressive Conservative Party of Canada in the
1993 federal election in the riding of
Waterloo, and in the
1997 federal election in the riding of
Kitchener—Waterloo; she was defeated both times. Woolstencroft served as a trustee on Waterloo County Board of Education (1970–1972, 1974–1985), including being elected chair from 1979 to 1982. She also served as President of the Association of Large School Boards in Ontario in 1984 and 1985. Woolstencroft served as a councillor for the City of Waterloo for three terms, from 1985–1988, 1988–1991, and 1997–2000. In 2000 she was elected as Mayor of
Waterloo, Ontario. Her tenure as mayor was dominated by the
RIM Park scandal, involving the financing of
RIM Park with a loan from MFP Financial Services of
Mississauga, a deal which had occurred before her time as mayor but which she had supported as a councillor. This ultimately led to a full judicial inquiry of the RIM Park deal, at which Woolstencroft testified and argued she had merely been a "peripheral councillor on this". During her time as mayor, the city of Waterloo entered into agreements that resulted in the establishment of the Perimeter Institute, the Centre for International Governance Innovation, and the Research and Technology Park at the University of Waterloo. In the municipal election of November 2003, Woolstencroft was defeated by former mayor and MPP
Herb Epp. == Death ==