Free "hacky" solution.
Use a caldav server system such as own cloud/next cloud /Google calendar then use https://sourceforge.net/projects/outlookcaldavsynchronizer/ to sync it up and down from outlook. Most cells phones support caldav either natively bb/iOS or with an app (droid). For android i use caldav sync adapter. Otherwise and exchanger server will do what you want out of the box but it's costly.
In short. Server hosts caldav calendar. Outlook uses a plugin to two way sync this calendar. Other systems can also two way sync this same calendar.
Some server software already have caldav ready to be enabled e.g. cpanel or synology nas
Edit: just saw Mac... Whoops not sure if the source forge has a Mac edition. But the principal's apply.
If you can connect to it with Outlook (caldav), you should be able to sync it with Outlook CalDav Syncronizer. Its not a server, but a plugin for Outlook that will sync to/from/mirror/merge/etc gmail/any caldav setup I have thrown at it.
I use it to backup calendar/contacts from my exchange env that I am decommissioning, to a mailcow install (that I am moving to) and to gmail (solely used for backup). I don't recommend syncing too often (like every 5 minutes) or Outlook starts to lose performance.
Just to add: if you prefer google tasks, there's a free caldav sync tool on Sourceforge that seems to work pretty well syncing regular (non-App) Google calendar, tasks and contacts to Outlook.
https://sourceforge.net/projects/outlookcaldavsynchronizer/
I personally find Outlook.com tasks superior (support for start time, category etc, and no 3rd party sync tool required). However, if you use an Android device, the support for Outlook.com tasks sync is spotty at best.
It's not free, it can only connect with Network Edition...
edit: if you still wanna do it on free edition you can go with IMAP+cal/cardDav, there is open source plugin for outlook for that. There is also z-push + zimbra backend for active sync.
Also we are moving away from this, as for the role we tried to implement it, it didn't work well and reputation seems to be irreversibly damaged. Hint, if you want separate ldap master, you need good stable connection between it and other servers in multiserver installation. Also one downed server can make the rest misbehave unpredictably. it's good for single server installs and for maybe having proxy/mailbox/ldap separate machines.