I know of only one song about well-dressing; "Five Wells" by Andrew Train, recorded by Ripley Wayfarers on their LP Five Wells. Traditional Sound Records, TSR013, (C)1972. As Giok puts it well, a bouncy morris-y tune, and specifically about Tissington, the chorus names the wells involved.

The group included Mick Peat, so he might prove helpful if you can reach him.