Need Advice: Two “weddings” in one weekend?

I feel like this is very close to a tiered wedding, with an A list and a B list. The A list gets all of the honours of seeing the wedding and having dinner etc. The B list is invited over to celebrate something they weren't invited to. Anytime you start to do that you're going to run the risk of hurt feelings. Etiquette-wise, tiered weddings are a faux pas.

I think you need to pick either a larger wedding or the immediate family/friends option if you're planning to use the backyard for sure. Also to note, you might want to look up what's involved in backyard events, as they are very involved to plan.

I'm glad you have a good idea of what's involved, because a lot of people have no idea what they're getting into with backyard events.

So essentially if both events on the weekend are parties then I don't see a problem with that. You're basically having two parties since you have it set up for more than one night. If you take the "wedding" aspect out of it, I think you're good etiquette-wise. Have fun with your planning!

Your idea of a two-part celebration with an intimate ceremony and reception on Saturday and an extended family reception brunch on Sunday is creative. Clearly communicate the plan to guests, emphasizing the significance of both events. Capture key moments during the intimate ceremony, and the Friday brewery gathering is a nice, optional touch for informal pre-wedding mingling.

So besides the fact that the title is misleading because neither are actually weddings I wouldn't walk down the aisle at either. If you want a big wedding where you walk down the aisle then I think you need to rethink your entire plan. I also don't understand why you'd have a court house wedding if you plan on reenacting the entire thing.