I can see where personality plays into it. I would say it sounds like in your closer circle you have your voice which is great. Most people are honorable people that do care about their neighbors/community so they will still listen if you say you are uncomfortable with something.
I wouldn’t worry about speaking up.
I have not yet been to BGW as we live in NJ, have underlying conditions, I am supposed to let my immunologist know if I've left the state, would need to quarantine for 14 days if I do travel to VA (I believe that restriction has loosened now) and find a 6+ hour drive a bit much for a shortened session. My husband and I would usually take three or more long weekend trips to BGW, and spend every moment from rope drop til close at the park every day.
So, I cannot comment on what it's like speaking up to people at the park. I have on occasion spoken up politely to people who refuse to wear their masks properly and go the wrong way up the aisle in our grocery store.They also broadcast over the PA about keeping 6ft from others and to please follow the arrows. A couple weeks ago, after such an announcement I said to a woman with a mask under her chin who was going the wrong way, to please wear her mask properly and follow the arrows. She screamed at me to f*ck off and mind my own business. Another woman who was behind me did not take kindly to that and started screaming at the offender. It was ugly. You never know how someone will react no matter how politely you ask.
Both my husband and I are now vaccinated so I'm hopeful we will get to F&W as that is always one of my fave events.