Aylward was born in 1955 as son of Bob Aylward. He attended Kildalton Agricultural College, Piltown.
From 1992 to 2007 he was a member of the Kilkenny County Council and served in this period from 2003 to 2004 as its chairman. He also belonged to the Southern and Eastern Regional Assembly in 1994 to 2004 the South East Regional Authority, and from 1999 to 2004. Again, he had each held the office of chairman. In the South East Regional Authority from 2000 to 2001 and in the Southern and Eastern Regional assembly from 2002 to 2003. From 1999 to 2004 he was director of the Port of Waterford. In Southern Fisheries Board Aylward from 2000 to 2007 member.
In May 2007, he was elected in the constituency of Carlow - Kilkenny for Fianna Fáil in the 30th Dáil Éireann. Originally, his brother and party colleague Liam Aylward was always begun in that constituency in the previous elections. As this, however, 2007 did not run, but instead ran his brother. In the next elections in February 2011 Bobby Aylward could not defend his seat and thus retired after four years out of the Dáil Éireann.
Aylward is married and has three children, two sons and a daughter.