Drumkilly always had a strong tradition for drama with Drumkilly hall hosting many theatrical evenings in the 1940s and 50s.

In September 1954 Michael Reilly( Curraghabreedin) and Paddy ( Lough) Smith held a meeting in Smith’s shop Derrin and the Milesian Players were formed.They decided to cast the play ‘The Blind Wolf’ and the following cast took part, Michael Reilly, May Smith, PJ Smith, Maggie Comiskey, Paddy ( Lough) Smith, Jeanie Smith, Maureen Cronin, Tom Cronin, Andy McGivney, Jimmy McCann, Denis King, with producer Michael Reilly.

The players entered the Cavan Drama festival in March 1955 won the Confined section and received the Alderman Hugh Lee cup and a nomination to the All Ireland Final in Athlone.

They did not win but the adjudicator Sheila Richards was complimentary of the performance. The tradition of having a drama group continued during Fr Young’s time in Drumkilly and the local troupe performed , ‘The New Gosoon’, ‘Sive’, ‘The Year of the Hiker’; and ‘Professor Tim’ in Drumkilly, Crosserlough, Mullahoran, Legaginny and Carrickallen.