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You can do so much more with your Mac’s Apple Calendar app than just create calendars and events. So if you’ve only skimmed the surface of the native macOS calendar so far, let’s delve deeper into it with the advanced Calendar tips below.
To catch up on the basics of the app, check out our Mac Calendar tips for beginners first.
1. Add Multi-Day Events
Did you know that you can add multi-day events to a calendar with a simple click-and-drag action? To begin, in the Month view, click on the first day of the upcoming event, drag the cursor all the way to the last day of the event, and then release the cursor. Calendar then schedules the event as all-day sessions spanning multiple days.
To schedule multi-day events in the Week view, drag across the relevant consecutive days in the all-day section at the top. If you click and drag across days in the sections below, the event gets scheduled between the first and last time slots on which you’ve clicked.
2. Add Events From Mail and Notes
Wouldn’t it be convenient if you could add email invites to parties, meetings, and other events to your calendar without leaving the Mail app?
That’s indeed possible, but only after you enable a checkbox under Mail > Preferences > General: Add invitations to Calendar automatically.
After tweaking this setting, when you hover over a date/time snippet in any email, you’ll see a marquee selection appear over it. When you click on the tiny down arrow button next to the marquee, Mail lets you add that event to the Calendar app from a popup. (See the screenshot above for a sample view of the Add to Calendar popup in Mail.)
Since you can schedule only upcoming events, the marquee selection doesn’t show up for dates in the past.
The Notes app also allows you to turn dates and times in your notes into events. The process is similar to the one in Mail, but it involves an additional step. Here, when you click on the button next to the marquee selection, you’ll see a small popup menu. You have to click on the Quick Look Event option in this menu to reveal the Add to Calendar popup.
3. Set Reminders for Birthdays, Meetings, and More
If you want to, say, receive alerts about someone’s birthday or reminders about upcoming flights, you can program Calendar to deliver them.
The app lets you set up alerts while adding events to your calendar. If you skip adding alerts, you can still go back and add them later. To add an alert to an existing event, first double-click on the event in your calendar to open the Edit Event popup.
Next, click on the date and time section in the popup to reveal a hidden section. There, from the alert dropdown menu options, select when you want Calendar to send you an alert about the event. After you select an option, you’ll notice a plus button show up next to the new alert. That button, as you might guess, lets you create multiple alerts.
For events in need of recurring reminders, also choose a suitable option from the repeat dropdown menu.
The combined setup of the alerts and repeat dropdown menus comes in handy for birthday calendars. With this setup in place, Calendar creates new items for the recurring event automatically and also sends you birthday alerts on time.
If you need a more robust reminder system, check out these great reminder apps for macOS.
4. Open Files and Apps on a Schedule
Let’s say you work on a certain PDF invoice template on the first day of every month before sending it off to a client. Or maybe you need to have certain files ready to go before every meeting. For such repetitive tasks, why not program Calendar to open up the associated file(s) automatically on a schedule? That’s easy to do.
To get started, create an event for the task and then double-click on it in the calendar to open the Edit Event popup.
In the popup, click on the date to reveal the hidden options, then select the Custom option from the alerts dropdown menu. You’ll then see another tiny popup appear. In this second popup, click on the Message with sound dropdown menu to reveal the Open file option.
Once you click on Open file, a new dropdown menu appears, from which you can select the file (or app) that you want Calendar to launch automatically. Tweak the other dropdown menus available to specify when exactly you want to bring up the file and hit the OK button to wrap up.
Notice the plus button that shows up next to the first alert. Use that to create alerts to launch multiple files/apps, one alert at a time.
If a certain file didn’t open on schedule, check if Do Not Disturb was active on your Mac then. If scheduled files are not opening at all, see if you have hidden notifications/alerts via Calendar > Preferences > Alerts or under System Preferences > Notifications > Calendar.
5. View Events as a List
It’s nice that you can see events laid out for the entire week or month in Calendar. But what about when you want to view them as a list or an agenda? Calendar doesn’t have a one-click view option for that.
But you can use this hidden workaround for a makeshift list view: type a double quote (“) into the search box at the top-right of the app and hit Enter. This reveals a scrolling list of all your events—past, present, and future—across all calendars. That’s handy, right?
6. Hide All-Day Events
When you’re taking in all your scheduled events at a glance in the Month view, all-day events such as birthdays and tasks can be distracting. But you can hide them temporarily with the View > Hide All-Day Events menu option.
To reveal them again, click on View > Show All-Day Events.
7. Let Another Person Manage Your Schedule
The macOS Calendar lets you delegate your calendar-management tasks to someone else, such as a colleague.
To bring in another person to view and edit your calendar, visit Calendar > Preferences > Accounts. There, select an account in the sidebar and click on its Delegation tab in the right-hand pane. The Edit button below this pane lets you grant access to your calendars for that account.
Click on it to start adding the name of the person whom you’d like to invite to manage your calendars. Be sure to select the Allow Write checkbox if you want to grant edit privileges to the delegate.
How is delegating different from sharing in Calendar? When you share calendars, you’re granting access to selective calendars only. But when you delegate, you’re sharing all calendars associated with a particular account.
Note that certain calendar accounts don’t support delegation. You can rely on the Delegation tab for such accounts to tell you so.
Apple Calendar: A Smart Free Calendar App for Mac
Calendar seems like a barebones app when you open it for the first time. But as you get to know it better, you’ll appreciate that it has so many useful features tucked away here and there.
It’s a pity that Calendar doesn’t give you a quick way to add reminders from the macOS menu bar. But as always, “there’s an app for that.” We’re referring to Itsycal, one of those tiny time-saving Mac apps you’ll fall in love with. Itsycal syncs with Apple Calendar and lets you add Calendar items from the menu bar!