Autumn is well and truly with us here, as the cooler, rainier weather and the fall of leaves demonstrates: "Season of mists and mellow fruitfulness, / Close bosom-friend of the maturing sun;" has been the couplet (by Keats) on my mind.
How then is autumnal May Mary's month? Primarily, I would hazard, because it is part of Eastertide, and Our Lady is the supreme masterpiece of Christ's Victory: not only redeemed, but perfected from the first moment of her existence; not only saved from every fall into sin, but preserved, "spirit, soul and body", and already assumed in body and soul into that perpetual triumph and glory which will be the lot of the Saints after the General Resurrection.
If Christ is the First-Begotten from the Dead, His Virgin Mother is the signal exemplar of His grace. She is God's masterpiece, and so it behooves us, at this season of rejoicing, to rejoice and be glad in her: Gaude et lætare, Virgo Maria, alleluia: Quia surrexit Dominus vere, alleluia.
It is a pious belief and well-founded that Christ, rising from the dead, went first to His Mother to shew her that He had returned: this rewarded her great faith, in that she alone did not despair at His Death, but knew that He would rise again. Hence, when the holy myrrh-bearing women found the tomb empty, He was to be found (as decades before at the Epiphany) "with Mary His Mother". Mary Magdalen was rewarded for her penitent zeal by beholding Christ Risen; but Christ's appearance to the Immaculate Virgin necessarily preceded His appearance to the Magdalen.
This May, we sing Regina cæli thrice each day until its very end, for those following the Traditional Calendar; and the 31st of May is very fittingly kept as the feast of Our Lady as Queen: for such a great Lady is very obviously a Queen, just as Christ is the true King. May their reign extend into every heart!