It is an old tradition and norm under Church law to allow a priest to celebrate three Masses on All Souls. A lot of folks will be puzzled by this: why "allowed"? Isn't a priest always "allowed"--even encouraged--to offer more Masses day-by-day? The answer is no; the norm is to offer Mass once a day during the week, and perhaps two in need; twice on Sunday (for the sake of the people), three times in need. "In need" is the rationale for priests offering even more Masses, daily or on Sundays and holy days--but the value at stake here is to emphasize the specialness of the Mass and to preserve the priest's spirituality, of which the Sacrifice is the core, by not having him "crank them out."
So why the exception for All Souls? (And also for Christmas, if memory serves; parish priests tend not to worry about these things, because we seldom lack for opportunity to celebrate additional Masses!) For the good of souls, particularly the holy souls in purgatory.
As All Souls fell on a Sunday, the opportunity to offer three Masses was no trick--I had the 4 pm Mass on the Vigil (I am puzzled by the bishops said the Saturday evening Mass would be for All Souls, when All Saints outranks it, but again, I don't have time to puzzle over such things; perhaps I missed something), then the 9 am Mass on Sunday, and then a special, 7(-ish) pm Mass with the high school group. This is our Life Teen group; I thought you might be interested in how our "Life Teen Mass"--first ever--went.
Our excellent coordinator of religious education and youth ministry has wanted to have an evening, around Hallowe'en, on which we'd turn the basement of the former-rectory-now-parish-offices into a "catacombs," and have the high schoolers gather there, after dark for catechesis and perhaps Mass. We'd talked about for a couple of years, but didn't do anything until this year.
I was reluctant to have the Mass in the basement of the building--there is no altar there, no chapel, and one has the Mass outside a sacred place only for very special reasons. There were certainly practical reasons as well--no ventilation--but I can see why he liked the idea. Well, instead, we decided to have a period of catechesis in the "catacombs"--including the basement's whitewashed walls adorned with early Christian symbols--about this part of our history. Then we had a candlelight procession from there, outside, and around to our perpetual-exposition chapel (also in the basement of the church), for Mass. As we walked, we sang a Litany of the Saints.
Mass was not terribly out of the ordinary; I would like to have used incense, however the chapel is a very close space, and we do have at least one high-schooler who has serious allergy issues. We did chant many of the prayers, including several in Latin--the Sanctus and the Agnus Dei. I gave the homily you see below, but added some about Hallowe'en and emphasized the idea of our joining a procession of the faithful that stretches across the ages, and forward into eternity, connecting to the catechesis we'd had beforehand. I used the Roman Canon, which has so many saints included.
We had over 20 of our high-schoolers turn out, plus a number of adults, about 30 in total. Not a lot by big-city standards, but good for us. At the conclusion of Mass, I mentioned to those present that next week, I'd do a "dry Mass" (meaning not an actual Mass, but a "show-and-tell" explanation of Mass) and that being part of that would be an excellent follow-up. And I pointed out one of the ways the Mass itself shows evidence of being a procession, reaching way back; we used four languages at Mass: English (rooted in the present); Latin, taking us almost all the way back; Greek (Kyrie) which is the language of the New Testament, and Hebrew (Alleluia, Amen), taking us back to the liberation of God's people from slavery.
Oh, and yes, I used black vestments.
No, we don't routinely do a Sunday evening Mass. Many would like it, but for a number of reasons, I have declined to start one. But a one-time, or once-a-year thing, is a lot easier to say "yes" to.
Before and after Mass, we had a fire going outside--with a parent keeping watch, have no fear!--which provided an opportunity for 'smores' after Mass while we waited for the kids' parents to pick them up.