Ledges. Find a ledge that you would be able to ollie onto. Get some speed and approach the ledge facing it and at a smal angle. Once you are along side with it pop your ollie and bring your back trucks on tops of the ledge than your front truck. You have ollied onto a ledge.
Boxes. Ollieing onto boxes is all about timing. Find a box that you can ollie onto. Then a approach it at comfortable speed. As your about a foot and half in front of the box pop your ollie. If its a high box make sure to keep your knees extra bent. Land on the box.
Rails. There are many different ways you can grind on a rail but for now we are going to focus on a very basic grind called the 50-50. Find a rail that you can ollie onto. Approach the rail at a comfortable speed and at a little angle ( note you should be facing the rail). Pop your ollie just a little higher than the rail and lock your back truck onto to it, then your front one. You ollied onto a rail.
Being able to use you ollie to ollie onto ledges, boxes, rail, will allow you to be able to skate more obstacles as well as open up new tricks for you to learn.
My Big Tip:
My biggest tip would be to be 100% confident with your ollie on flat ground before trying to ollie onto objects
Question: I can’t lock my trucks onto the rail.
Answer: This is a very common problem. A good way to get better at locking your trucks onto the rail is to move the rail onto the grass and just practice ollieing and locking your trucks onto the rail on the grass.
Question: I have trouble landing my ollies on boxes. I can get on top of them but i just can’t land them.
Answer: Make sure you keep your knees bent instead of extending them for the landing.
Source by Bob Slattter