Twenty three gully heads were randomly selected from a representative gully basin at Ganganir Danga, Paschim Medinipore West Bengal for understanding mechanism of gully head retreat. The study was made during June to September, 2011. Height and slope of gully heads, width at top and base of the gully head were monitored. Geotechnical properties of soil like cohesion and angle of internal frication, bulk density were measured to estimate shear stress and shear strength at gully head. Linear retreat of the gully heads was monitored by pegging technique. Depths of tension cracks were measured at regular interval. The study shows that, gully heads retreated at different rates ranging from 13 cm to 121 cm depending on instability factors. Gully heads are few times steeper than angle of internal friction that introduces instability. Alcove structure and plunge pools, developed at the bottom of gully heads, lead to formation of overhanging slope. Near vertical and overhanging slope of considerable height develop tension cracks leading to mass failure and gully head retreat. Number of instability factors is operating at the gully heads and no linear relation can be established between these factors and gully erosion.