As skateboarders gather experience, they start attempting advanced tricks and maneuvers. Of these, the most popular are the aerials. Ollie is one of the most advanced and popular skateboard tricks. Legend has it that it was invented by Alan Ollie Gelfand. By using this technique the skateboarder jumps over, onto or up to an obstacle. Throughout the exercise the board appears to stick to the skateboarder's feet. The Ollie is the basic skateboard trick, from which others can follow. But remember, it is not at all easy and takes long hours of practice to learn!

The board flip is another maneuver that is very popular. In a well-performed board flip, the skater completes a landing back onto the deck after the board turns one or more time under the rider's feet while both are in the air. Board flips can be of various types.

Another common and popular trick is known as a grind. A grind is performed by directing one and sometimes both trucks onto an object that has a distinct edge. The object may be a curb, railing, or pipe. The rider and skateboard are on the move, while the metal hanger scrapes along the edge. The grind is completed when the rider pops the trucks off the surface and re-engages the wheels.

A half-pipe offers a stiff challenge to skateboarders. Riders propel themselves up and down the curves of the trough while inside a half-pipe. In some of the half pipes the walls are almost completely vertical, where skateboarders can show difficult maneuvers, usually called vert skating (short form of vertical skating). In vert skating, skateboarders propel their boards to the top of either wall, perpendicular to the ground. They perform skateboard tricks on each side while riding back and forth. Skateboarders also perform other moves such as hand plants, foot plants, inverts, and flips. The McTwist is considered to be the most radical of vert maneuvers.