To answer some of your questions, it’s not like every off road event, but it’s like some (vague, I know). At some events people just kind of camp and hang out and don’t really hit trails, whereas at The Pilgrimage, there is a strong emphasis on getting out into the beautiful class 4 roads with others.
People are generally excited about meeting new people and those who have some experience are often glad to assist first year people. When I was new to it (back in the VT Overland days) someone took the time to make sure I was able to go out with others and enjoy the event and the people I am with are glad to pay this back. It’s good to decide how much you want to be on actual trails, vs how much you want to see some sights (Hillfarmstead, Woodstock, Barnard general store, etc) so you can aggregate like minded people.
The base camp is spartan, (no showers, flush toilets etc) but has plenty of firewood and coffee and bsandwiches in the morning. There are a few vendors (Orvis, VT Creamery etc) and generally a food truck or two each evening. There is a quiet area, if that’s important to you. People camp in everything from Earthroamer type rigs to a sleeping platform in their truck, so whatever you want.
My advice is to show up early, set up camp and walk around meeting people as they come in. It’s fun to look at the rigs and you’ll probably get a feel for people who will be suitable trail buddies (ie, if you’re in a stock 5th gen 4runner, probably don’t plan on hanging out with the Jeeps on 39s). Be honest with your tolerance for possible damage to your truck, there is nothing wrong with sticking to only green trails, and plenty of others will join you. That said, if you want to do reds and pinks, be open to using spotters.
There is only a set schedule for organized rides, otherwise you can leave at 5am or noon and arrive at dusk or at midnight, mom is not waiting up (my personal preference is to get back at last light).
As far as equipment, there are few need to haves, but a lot of nice to haves. A GMRS radio is at the top of that list. Obviously recovery equipment of your choosing, compressors, tire deflators, etc are nice.
Anyway, it’s just a few thoughts, hope it helps.