In 1912, Bennington went to the Hingham Show, where he heard Billy Cooper playing the dulcimer.
Cooper's father was bandmaster of the Hingham and Watton band, and Bennington took lessons from him.
Bennington frequently rode a bicycle with his dulcimer strapped to his back, with the ends sticking out above his shoulders.
He played a wide range of tunes, including hornpipes, polkas, schottisches, jigs, and marches.
Bennington spent most of his life as a gardener, and continued to perform well into his eighties at local folk festivals, frequently accompanied by his wife Iris.