Uuuh! This sounds like a lot of fun. I have been to the Octoberfest a few years back while working for a Munich company. I am also trying to convince my managers that I need a trip to our Munich offices in September. However I am not sure timing will work since we just had some delays. Maybe October is better anyways, the traditional Octoberfest Dresses will be on sale then and I can add a second one to my collection.
Munich during Octoberfest is incredibly packed (mostly with drunk people).
If you are into hiking, there are plenty of opportunities around Munich. Munich itself offers tons of Museums, I can particularly recommend the Science Museum. I am not too much into Arts but there are many awesome galleries and museums too.
If you are going to get an Octoberfest Dress, just keep the "relationship status" in mind: Bow on the right means in a relationship, on the left means single and in the center means "It's complicated"... Hahaha... Apparently this is still a thing.
That is me in a traditional Octoberfest dress (actually bought in PA but German made) before attending our local Octoberfest in VA...
Unfortunately while I do know a bunch of people in Munich, they are all cis...
Hope someone else replies.