D&D 5E Question: how do you determine an adventure site's CR?

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One technique that is used in Princes of the Apocalypse (so I've heard) is to assign adventure sites a challenge rating. This idea is nothing new to old time gamers and is also used in video games. It is a useful tool, especially for DMs running a more sandbox/modular style of play.

So my question for other DMs / adventure designers is: in 5e how do you assign a CR value to an adventure site?

Do you base it on the highest CR monster found there?

Do you assume a certain encounter as a model, then use the encounter design guidelines to determine the difficulty of the site for a group of four PCs of level X? Or perhaps do the same for an average of all encounters in the area?

Do you use some kind of voodoo?

What if the site has multiple CRs based on which area/level you're in? Break it down into sub-sites?
 
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