May Day celebrations have taken place across England for centuries. Although May Day has been banned in the past, festivities have been revived and developed in recent times.

It is thought that the Jack-in-the-Green custom originated around the 17th century from the milkmaids and chimney sweeps of London. As part of the May Day processions milkmaids would carry milk pails decorated with flowers and silverware. Over time the pails were replaced with decorated headdresses. Not to be outdone, chimney sweeps began creating garlands, which became bigger and bigger until the frameworks of greenery and flowers covered an entire man, a Jack-in-the-Green.

There were at least two groups in Hastings and St Leonards that paraded a Jack-in-the-Green until about 1889. The tradition died out nationwide in the early 20th century. Since the folk revival on the 1970s many customs have been revived. Hastings Traditional Jack in the Green was revived in 1983 by Mad Jack's Morris who gave 'Jack' his own face and have helped host the event ever since.