I was able to build Wine 64 bit from source on macOS Catalina and successfully run Notepad++ 64 bit on it.
My steps were more or less something like that:
- Download Wine 4.20 from https://dl.winehq.org/wine/source/4.x/wine-4.20.tar.xz
- Extract it
- In terminal go to extracted directory
- Run: ./configure --enable-win64
- It showed that it couldn't find bison, so I installed it with macports (sudo port install bison).
- After I was able to run ./configure --enable-win64 successfully without errors in terminal run: make
- It compiled after more than 30 minutes.
- I run it with: ./wine start
- It opened windows console and here I was able to cd to Notepad++ 64 bit directory (downloaded from https://notepad-plus-plus.org/repository/7.x/7.0/npp.7.bin.x64.zip note that newest version did not work and threw some errors about some dll's)
- I typed notepad++ to run exe file
- It showed some errors about freetype fonts so I installed them with macports and I had to copy them from /opt/X11/lib to /usr/local/lib before wine detected them
- After fixing freetype fonts problem I was able to run notepad++
- Also you might want to run: sudo spctl --master-disable to disable gatekeeper if you will see some system alerts about loading app from unknown developer.
- Also note that instead of ./wine start you can run ./wine explorer for graphical file manager instead of console
Those steps might not be exactly precise, as I'm not sure if I did not miss something but hope it will help someone.
Also note that obviously wine on macOS Catalina will be able to run only some 64 bit windows apps and all 32 bit windows app will not work. I also tested it with IrfanView 64 bit (https://www.fosshub.com/IrfanView.html?dwl=iview453_x64_setup.exe) and it also works fine.
In case you wanted to get wine working for purpose of running 32 bit games then unfortunately it will not work with wine but you can try with virtualbox. You can check https://www.youtube.com/watch?v=3AO8dF0vviQ for some performance improvements tips (in brief: using VM with retina disabled, VboxVGA setup, disabled mouse integration, limiting FPS with RivaTuner).