Not everything that leaves your computer is encrypted. Yes most things are, but you'd be shocked at how frequently third party apps either aren't encrypted or instantiate their background fetching services with HTTPS but with bypassing of cert checks enabled. There was a torrenting app a while back that fetched software updates over this kind of fake HTTPS and it was actually used to deliver some of the very first ransomware for macOS. Similar mistakes can happen on any other platform.
There's other user-error factors too. One example is what I mentioned before. If your captive portal detection fails and triggers on the first HTTPS site you visit, a lot of users will begrudgingly click through the certificate warnings to get themselves online. On many OS'es that results in permanently trusting that cert.
You can also put your privacy at risk -- often times IPv6 addresses contain your MAC address and other non-randomized information about you. Heck just joining a network turns off almost every OS's anonymizing MAC address features, which allows location analytics software running on the wifi to monitor your movements and behavior. Target, for example, deploys two APs next to each other (look up at the ceiling next time at Target). One serves you free wifi, and the other is purely dedicated as a location sniffing radio to monitor where shoppers spend the most time.
With that said, I use free wifi all the time. I understand most of these risks and think I practice good enough computing habits that I don't feel affected by these risks, or I understand them and simply don't care. Heck one time I saved on laundry detergent at Target by following some instructions to open the app and stand by the detergent aisle for 5 minutes without moving anything on the shelves. Sure enough I got a coupon emailed to me. Creepy but I don't really care about my store tracking me if I get something in exchange