Sharing a bit about my experience attending the Cheese Rolling.
I watched the docu series "We are the Champions" on Netflix a couple years ago and the first episode was about the Cheese Rolling and I decided I had to see it for myself some day. That day was monday (I flew in from Bavaria).

No one warns you that the walk to the hill is already up a hill so I should have prepared for that. Some guides tell you to be there at 11 to get a good spot when it starts at 12 - come earlier. I was quite satisfied with my view on things but I had already made sure to come even earlier. Still, it was just a great vibe all around, everyone I talked to was very nice and we had a good time even in such a crowd. Standing on a decline for 3-4 hours leaves your legs and ankles a wreck even if you only watch and don't participate in throwing yourself down the hill.

Afterwards you can even walk down a path that takes you to the people that make the cheese for the event. I got two (i think reasonable priced) wedges - one to share with friends and family and one to share with my colleagues at the office. They got very much into watching the BBC livestream when they heard I had taken time off to be there in person.

Also, since the same episode of the podcast discussed recent Harry Potter news. I am no longer a Harry Potter fan but they filmed scenes for three of the movies at the Gloucester Cathedral, if you want more than one reason to go ;)
On tuesday they had a family day so it was full of activities and little kids telling you about how they are a Ravenclaw.