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@elisha-starquill

One of the most useful “general guides” on medieval military strategy and tactics has been Christine de Pizan’s The Book of Deeds and of Arms and of Chivalry – there’s a modern English translation of it available (it was originally a military manual written in French in the early 15th century). If you want to get REALLY old school, there’s always the De Rei Militari, which is a Latin military manual of strategy and tactics from the Roman period which medieval commanders then had copied and studied for the next thousand years. But Christine de Pizan is just as informative and the translation is very accessible and readable (and some of the shenanigans that ancient commanders pulled just make your eyes roll.) Machiavelli’s The Prince is also indispensable when considering medieval / renaissance realpolitik, and also contains some insights on broader strategy (though not as much in specific battle tactics; Machiavelli was an administrator, not a general).

Wikipedia is also a GREAT place to read about battles if you don’t want to spend any money. Some of its articles feature extremely detailed breakdowns of the terrain, weather conditions, force compositions, background, phases and movements of battle, etc.

Okay, my analysis of your battle set-up:

The valley, forest, constrained battle space – there are many similarities to Agincourt here, down to the outnumbered defenders needing to achieve a break-through against superior opposition. However, it sounds like the bad guys also control the heights since the good guys have been surrounded, which is BAD. Look at Dien Bien Phu (1954) to see what happens when you cede control of the heights (granted, that was a battle with modern technology, but it applies in any setting featuring any amount of ranged weapons or artillery).

What is the force composition of each side? What kind of troops, weapons, magic gizmos, etc. does each side possess?

Do the bad guys have lots of cavalry, infantry, missile troops, artillery?

What troops do the good guys have? Same question.

Whichever side has superiority in missile fire has the ability to force battle by bombarding the other side; at that point, the other side must either withdraw to better defenses or engage their attackers. At Agincourt, the English harrassed the French with arrows until the French knights got tired of being shot at and mounted a hasty, disorganized cavalry charge, uphill through muddy terrain against prepared defensive positions (hedges of sharpened stakes) that negated their mounts, while enduring a hail of thousands upon thousands of arrow shafts.

Now, if the bad guys are gathering reinforcements, your two heroes could potentially try to disguise themselves as soldiers and participate in a frontal charge – but they would need some way to identify themselves to the good guys before they, you know, get shot/stabbed/trampled underfoot.

Alternatively, if the bad guys have a central “main camp” where the bulk of their forces are gathered and their command structure is centralized, the good guys could try to hit that point with all their might to force the enemy to gather their forces to defend their command, thus weakening the perimeter security enough that the heroes might be able to slip in or fight their way through.

Another idea is that the good guys have an advantage in either cavalry or missile weapons with irregular crack troops (think merry men of Sherwood, poachers, raiders, etc.), they might skirmish with the enemy line under cover of night, launching multiple attacks to cause chaos and confusion amongst the enemy as each section commander of the perimeter receives conflicting reports about who, what, and how many are attacking. This would provide an opportunity for the heroes to sneak in, but they would need to be aware of the plan – or else they might just sleep through it.

 

I know you said the good guys can’t receive reinforcements, but if they have any allied forces at all outside the perimeter and they have multiple layers of strong defensive positions around the portal, they might be able to pull off what William Marshal did in the Battle of Lincoln – crushing a superior force by catching it in the midst of an assault against a small garrison force, breaking their morale by attacking them from their undefended rear and cutting off their route of escape. Now, against vastly superior numbers, all that might do is buy time for the heroes to slip in amidst the confusion, but that might be all you need. Plus, you then get the dramatic sacrifice of some noble companions who gallantly go to their deaths in a heroic last charge! ( 😀 )

https://en.wikipedia.org/wiki/Battle_of_Lincoln_(1217)

 

The above ideas aren’t the only ones – I’m sure I could glean more with more time. But bear in mind that numbers are a huge advantage in battle – the good guys’ victory hangs on a gambit. All of these above ideas are gambits, and whatever plan you use in story should convey that it is risky and likely to result in heavy casualties. This final battle sounds like it is meant to be a last desperate bid for victory, and accordingly, should feel hard won – or at the very least, expect it to be a pyrrhic victory.

And I would love to see your future draft(s) when they come out!