Headteacher John Fisher is spending half-term busking and performing in pubs to raise cash for his Oxfordshire primary.
He is currently on a week-long tour of England, hoping to raise Pounds 50,000 and public awareness of teachers' problems.
Mr Fisher, the guitar-playing head of Rush Common school in Abingdon, has had the budget at his 483-pupil primary cut by more than 8 per cent in the past two years.
"We have got flat roofs which are full of holes, the woodwork is appalling and have to put buckets out to stop the rain. This idea was born out of sheer desperation and a lot of frustration. We have written to MPs and county councillors. We have lobbied in London and outside the county offices but basically there is no funding available. I want people to know that teachers are doing very hard work and are worth their weight in gold."
Mr Fisher has been joined on his tour by Colin Miles, a banjo player who he has been playing with for 18 months. They perform as Paddy and Taff (Mr Fisher is Taff) and regularly play in Oxford's Rosie O'Grady's Irish pub.
This week's tour has been based around four Rosie O'Grady pubs in Oxford, London, Durham and Liverpool. It will also take in Nottingham, Newcastle, Carlisle and Coventry. They have also performed alongside the best of street entertainers in London's Covent Garden.