Jot The Date
(Free) This freehand calendar is a great option for iPad Pro users with an Apple Pencil. JotTheDate has the Magic Marker look of the calendars of yore you used to pin to your cubicle wall, allowing you to fill it with the personality of your busy, messy life. This app syncs with Apple's Calendar app, so you can see events from all your calendars alongside your handwritten scribbles and doodles. The app supports pressure sensitivity so you have control over the shading of your drawing. You can also switch between day, week, month, and year view as well as list view to control how much information you see.