The earliest recorded association of Mary with the month of May is found in the thirteenth-century Cantigas de Santa Maria of Alfonso X. St. Philip Neri, sometimes credited with beginning the May observances in Rome, encouraged young people to gather for floral and musical tributes to Our Lady. In Rome and other parts of Italy, customs and observances marking May as Mary's month spontaneously arose in families and religious communities.
Cardinal Newman observed that May belongs to the Easter season: the great feasts of the Ascension, Pentecost, and, not infrequently, the feast of the Holy Trinity are in May. "It is the time in which there are such frequent Alleluias, because Christ has risen from the grave, Christ has ascended on high, and God the Holy Ghost has come down to take His place. Here then we have the reason why May is dedicated to the Blessed Mary. She is the first of creatures, the most acceptable child of God, the dearest and nearest to Him. It is fitting then that this month should be hers, in which we especially glory and rejoice in His great Providence to us, in our redemption and sanctification in God the Father, God the Sun, and God the Holy Ghost" (Meditations and Devotions, Pt. I. The Month of May [London: Longmans, Green, 1920]).