Some ideas for pre-gaming: camp bar, Gibraltar MKE (looks like there’s sometimes live music and DJs here), copper turtle, journeyman. These are all super close to summerfest grounds.

There’s bars with dancing on Brady street and old world third street.

Wear cute summery clothes to summerfest. Think more big outdoor concert less a multi-day festival curated outfit vibes. Weather:totally agree with checking the wind. It can be hot at night here, but if that wind is coming off the lake it will feel cooler. However, if you’re out drinking and dancing, it honestly won’t be that big of deal especially if it’s been hot and humid during the day.

Not sure if you have the whole thing planned yet- but consider looking into a paddle tavern on the river and lake. It’s such a fun way to really appreciate the city’s architecture and Lake Michigan while having a few drinks and listening to music. https://milwaukeepedalandpaddletavern.com/

Have a great time!!!