In the Battle of Hackam Heath, we know that the beginning of this book happens roughly a year after Tournament at Gorlan.
King Oswald died in the first weeks of the year, so that would mean January/February.
Two months later Duncan announces that the queen is pregnant. It is mentioned that it was in spring - that would mean March/April. Halt also becomes the Redmont Ranger.
We know that four months after that, Halt goes to the mountains to investigate Morgarath’s army. That would make it July/August. Rosalind is 7 months pregnant by now. It is mentioned that it’s time of the harvest. According to a history website, there were two harvests in the Middle ages. The first one was in June and it was mainly for hay. The big one, which I assume we’re talking about here, was at the end of summer during August and September. So let’s make this August because it fits into the timeline.
Rosalind gives birth in her 8th month, so we know that a month passed, so now it’s September. That makes Cassandra a September baby.
Now it gets tricky. We don’t really know if it was a beginning of the month, the middle or the end, so here’s where we have to count. We don’t actually know how much time has passed between the moment when Crowley returned with Cassandra and when they move with the army, but it couldn’t have been much - a day max. Then we have the time until the Battle of Hackam Heath which happens a week after that (if I didn’t miss anything in the book). Then, three days later Daniel saves Halt’s life and dies. Halt is unconscious for a day and a half and the next morning he follows Jerrel and Kord. So six days after the big battle, Halt finds Will and his mum.
We know that by the time Daniel dies he knows about his son, so we can assume that when he left for the war, Will was already born or his wife was due any day. Also, in Ruins of Gorlan, it is said that Will came to the Redmont Ward as a newborn baby. Now, newborn means a baby from the birth up to a month old.
Since we don’t know the time of the month, we can’t really determine when he was born, just a rough month.
Should we assume that it was:
The beginning of September when Cassandra was born, (that would mean it’s be the middle of the month when Halt found Will), he could have been born anytime from the middle of August till the middle of September
The middle of September when Cass was born (with Halt finding Daniel’s family at the turn of September/October) Will would have been a pure September baby
The end of September (Halt finds Will in the first two weeks of October), Will could have been born anytime from the middle of September to middle of October)
Now, at the end of Ruins of Gorlan, Halt says that Daniel told him he had a wife with a baby due any day. Now we can safely say that we don’t have to count with the one month period of newborns since it couldn’t have been more than two weeks since Daniel left her to go to the battle (and since it took Halt one day to get there from the Hackam Heath I’d say it’s not far).
With this knowledge, if we go by the distinction we did above, if
Beginning of September (Cass is born) - it’s the middle of September when Halt finds them -> Will was born in the first two weeks of September
Middle of September (Cassandra is born), it’s the end when Will’s mum dies -> Will was born in the last two weeks of September
End of September (Cassandra is born), Halt finds them in the first two weeks of October -> Will could’ve been born in the end of September or the first weeks in October
Since king Oswald died in the first weeks of the year, I’d say he died in the mid-February (since we know about that the harvest is in August, it would fit the timeline), so that would mean that Will was born either in the beginning of September or at the end of September, making him a pure September baby. But this last paragraph is purely my own opinion and isn’t based on anything in the books so I have nothing to support that claim
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