The past-president of the Society of Education Officers used his review of the year to criticise Mr Woodhead for moving into "an overtly political arena".
Tony Webster, education director in Tameside, said he had become concerned by the increasing politicisation of what had always been an independent and non-political office.
And he voiced serious reservations about the independence of any review that OFSTED might carry out into the work of local authorities.
Mr Webster said: "The issue by HMCI of a pamphlet on education through an avowedly political source seems to me to threaten to bring the office into disrepute.
"The role of HMCI as a catalyst and stimulator of debate is a vital one. However, I believe there are more productive ways of doing that than by pillorying teachers and by demotivating a profession on whose enthusiasm and commitment the education service relies."
His comments follow complaints from the Council of Local Education Authorities about the pamphlet Mr Woodhead wrote before Christmas for the right-wing think-tank Politeia.
The pamphlet, which attacked the education establishment, was cleared in advance with Gillian Shephard, the Education and Employment Secretary. But CLEA is to make formal representations to her claiming the pamphlet was "inappropriate".
Mr Webster said he did not wish to comment on the effectiveness of the OFSTED inspection process. "I support the idea of inspection but I support it as a part of a managed process with schools with continued evaluation, review and action.
"My concern is that the holder of the post of HMCI appears to have moved into an overtly political arena."
Further criticism were voiced by the new president, Heather DuQuesnay, who said that inspection arrangements often appeared to be crude and resource-hungry. "The act of inspection is both threatening and sterile if it does not feed strategies for improvement."
And Mrs DuQuesnay called for a spirit of partnership and mutual respect between OFSTED and local authorities.
"Much could be gained if the OFSTED data base, upon the evidence of which sweeping judgments may begin to be made about the relative performance of different kinds of schools, were opened up to local scrutiny."