This thread's right up my street, I love the way music takes me back to certain times in my life, and I have a few monthly or seasonal playlists.
Thing with Maiden is that I got into them when I was first discovering "my own" (as in, not popular or what my parents/friends listened to) music in my early teens and my listening habits were a bit scattershot. Because I was discovering so much new music at once and was easily distracted by other interests, I didn't really listen to a lot of albums in their entirety and wouldn't start to do so until I was in my late teens/early twenties, so there's a couple of Maiden albums that took a while for me to fully discover and so have songs that remind me of all four seasons*, or ones that are mostly in the same season save for one odd exception or two.
*Fear of the Dark being one of them. With online reviews being less-than-favourable towards it I didn't give it much attention, I first heard the title track in June 2010, then From Here to Eternity in November 2011, then finally started giving the album a chance in 2012, so the memories it brings back span all four seasons across over two years!
A Matter of Life and Death is an autumn/winter album... save for Out of the Shadows and Benjamin Breeg. I first heard the former one particularly rainy day in May and the latter sometime in August. The rest of the album is entirely wintery, the dark, heavier tone goes hand-in-hand with the cooler, darker months.
Powerslave is 100% a summer album... except for 2 Minutes to Midnight, which I first heard one day in February. It still works for the summertime though, the whole album is a bright, upbeat burst of youthful energy, I think the Egyptian sun blazing in the album art adds to that tone as well.
Brave New World is the same as Powerslave, save for the title track, which I first heard one September day. I think that song fits that time of year though, it retains the upbeat energy but has a melancholic and slightly darker edge to it. The tone carries over into the Dance of Death album, which is a late summer/early autumn album for me, save for Paschendale, which is so aggressively wintery that it feels like it doesn't belong on the album. My history teacher first played it to me one day in November, even so, because of Armistice Day anything WWI-related will always make me think of that month.
Somewhere in Time is 100% a winter album. Hell, because I first heard the title track one snowy night in December 2009 it's basically a Christmas album. Christmas is a very nostalgic time of year, and with the SiT tone being so incredibly Eighties I think it fits. It almost felt a bit wrong hearing the SiT songs played live in the middle of July last year.