D&D 5E The Sherwood Forest Scenerio - How would you do it?

Thanks to the power of the internet, I'm rewatching a favorite: Robin of Sherwood.

So in inspiration of this, I'm asking the following:

How would you do a band of merry men in 5e (assuming the PCs are said merry men)?

What party would you build?

what obstacles would you have to deal with?

What would be in the woods to help/hinder the party?

What magic would be expected to be used to turn Sherwood forest into a fortress?

How would gameplay change when you switch tiers?

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I'd start them off all as mundane folk: Fighters, Rangers, Rogues and monks. Any character with reasonable charisma and Perform can act as a bard. As they level, you can crank the magic up. Arcane tricksters, Eldritch knights and Rangers start getting spells.

At low levels, you are dealing with animals, survival and caravan guards. You are also dealing with having to disguise yourself to sell and buy goods in town and gather information. So, I like to think there'd be lots of opportunities to make contacts, make enemies, sneak into people's houses and find information and, generally, try not to get noticed/recognized by the local authorities.

At Higher levels, you start making a name for yourself so guards get tougher, they start hiring magicians, mercenaries start looking for you. They start messing with your loved ones in the towns and you need to rescue people, help the poor, break people out of prison etc...

As far as the forest goes. Mostly, it's just rumours of being haunted or enchanted. Really it was mostly bandits that kept people out and used the myths of the forest to keep people away BUT...when you go deep enough, things get weird.

Look at the spell Guards & Wards and apply its effects to the deepest reaches of the forest.

Maybe, at higher levels, there's a need to seek something out in the centre of the forest....
 

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