How to pray and meditate while saying the rosary?
It is such an easy question to answer, but to really find a Catholic source that actually answers it seems next to impossible.
There are lots of books out there about the rosary. But most deal with the glories of the Most Holy Rosary, it’s history, it’s promises accorded to those who pray it daily, etc. As for Catholic sources about actually how to pray and meditate on the rosary, these sources for some reason are not openly available. Whether that is due to the fact that Catholics are not interested in it or that many of us just like to say the rosary as is, I do not know.
Some years ago my former seminary rector, Fr. Augustine Kalberer, OSB, PhD of Westminster Abbey celebrated mass in my home parish on the Feast of the Most Holy Rosary. The topic of his homily was how to meditate on the Most Holy Rosary.
In his homily he basically shared the idea that there were three general ways to meditate while praying the Rosary.
The first one is somewhat alluded to in Peter Turner’s answer. It consists on pondering the actual meaning of the words one is pronouncing as one prays the rosary. This is generally good for novices that are just getting into the habit of praying the Rosary everyday.
The second manner/of praying the Rosary is to meditate in one certain biblical passages associated with the particular mystery one is reciting. This is called a scriptural rosary.
As one recites a Hail Mary one meditates on the word of God revealed in Sacred Scripture.
As a title of example here are the scriptural references for the first decade of the Joyful Mysteries, the Annunciation:
The Joyful Mysteries
Through the disobedience of Adam sin enters the world. Rom. 5:12
The Father sends His Son to save the world. Jn. 3:17
The Angel Gabriel is sent to a virgin named Mary. Lk. 1:26,27
The Angel tells Mary: “You are to have a Son and will name Him Jesus.” Lk. 1:31
He is the Son of God. Lk. 1:32
Mary consents: “Let it be done to me.” Lk. 1:38
God the Son becomes Man, in obedience to His Father. Lk. 1:35
By His obedience many shall be saved. Rom. 5:19
Mary becomes Mother of God. Lk. 1:35
Nothing is impossible with God. Lk. 1:37
The third way to meditate the Mysteries is definitely the the most profound and in-depth manner to do. The soul that is accustomed to pray and meditation delves into the rosary mysteries by placing himself into the mystery contemplated and getting totally absorbed into the sacred realities being pondered. Some (very few) find this way of meditation as being a sort of second nature!
Some Jesuits like to put this in the sense that we try to place ourself at the very scene that we are contemplating and in a sense become a participant in the mystery we are meditating.
I like to think of this as making myself a fly on the wall and watching the the Mysteries of the rosary unfold before me.
Sorry for the lack of genuine Catholic references, but if I find anything of value I will edit it in.
As a side note, one can obtain CDs of praying the rosary with the pope. They are great for praying the rosary in a car when it is good to have your hands free for driving and not worrying about counting.
Some other Catholic sources that may prove helpful are as follows: