Freestyle Skateboarding 101

It’s all too easy to get overwhelmed when you’re trying to get involved with freestyle skateboarding. There are just so many things to learn, so many options available; from decisions about equipment to what tricks to attempt, there’s a lot to think about. And until now, there’s been no intro course to freestyle, no “Freestyle Skateboarding 101”.

Well, don’t worry. We’re here to try to simplify this for you. The trick tips are all numbered, and for the best part, that’s a suggested learning order; starting at the very first tip and working through is not a bad plan. However, if you follow the path outlined below, you should become a competent and well-rounded freestyle skateboarder in no time1.

At least, we hope so, anyway.

Right: Denham Hill does a railflip after a long day under the German sun in Paderborn. Follow this guide and you too can get wildly sunburnt while flailing around to a Descendents song like a madman.

Denham Paderborn Railflip

Right: Denham Hill knows his stuff; here he’s doing a very sunburnt railflip in Germany. Follow this guide and you could join him in a year or two.

Denham Paderborn Railflip

First steps

It should go without saying that you need to be able to roll before you begin. This is a continuous process; the more comfortable you are on your board, the easier any freestyle trick will be.

We don’t currently have an instructional guide on how to stand on a skateboard and push down the street; if that’s something you want to see, leave us a comment below, and we’ll look into it.

Before you get into the tricks, you should have at least a moderate level of control over a skateboard. Aim to be able to:

  • Push yourself forwards in a comfortable and relaxed position
  • Roll comfortably at a decent speed without panicking
  • Carve – turn without lifting any wheels off the ground – in both directions
  • Tic-tac – lift the front end of the board and move the nose slightly in either direction before putting it down
  • Stop in a controlled fashion (ideally via foot-braking – lowering the pushing foot to the floor gradually)

This may all seem painfully obvious, but a lot of people see stationary freestyle tricks and start working on flipping a board around before they can even roll comfortably – and it shows. Learning to roll around will not only give you a huge advantage in terms of competence and confidence, but it’ll help you stylistically, too. Don’t try to run before you can walk – or railflip before you can roll, I guess.


Humble Beginnings

Once you’re starting to feel competent at basic skateboarding, it’s time to start engaging with the tips. There’s a bunch of board manipulation in the early trick tips on that page, but you can skip most of those at this point. Have a go at the following instead:

Wheelies Featured Image

Wheelies

Basic tail wheelies should be a cornerstone of every beginning skater’s repertoire, but they’re often overlooked. The problem is they take a long time to be competent at; they require a lot of persistence, and most skaters just want to learn something flashy instead. But don’t skip over these – if you start doing them early on, and even focus on doing them whenever you’re just rolling to the shops, it’ll teach you a lot about board control and balance which will help you no end later on.

Endovers

Endovers

The endover is basically an extension of the tic-tac; you’re going to lift two wheels off the ground and spin around on the other two. The key to this is that you have to make sure you’re able to spin a clean 180º in every direction and roll away cleanly; a lot tricks you’re going to learn involving rotation will benefit from you learning this movement now.

Rail Stand Tricktip

Heelside Rail

This is your first piece of board manipulation, and if you’re coming from street skating, it’s going to feel very unusual. It’s important you learn this one right; done well, it’ll teach you to stay in contact with the board throughout a movement, to control how you shift your weight, and get you used to gripping and pulling the board with your feet. Done badly, it’ll just be an inconsistent flip-and-catch movement, which will teach you very little. Don’t rush this one.


Finding Your Feet

Assuming you’ve learned the previous tricks to a decent level, you should now have a small set of key skills to work with. It might not seem like much, but those skills should set you up for some more impressive moves. The difficulty’s jumping up a bit, but don’t worry: everything that follows is just an extension or combination of things you’ve already done.

Walk the Dog

The Walk the Dog is the textbook “filler” move in every freestyler’s repertoire. This builds on the skills you just learned with the endovers, but also teaches an important lesson – stay light on your feet and take it slow. Rushing this will make you trip over yourself, so take your time; smoothness comes from steady movement, and speed will naturally follow later.


Walk the Dog Thumbnail

Tailstop Fingerflips

This is going to be your first proper flip trick. I always show people this early on because you’re starting from a stationary position (and therefore not worrying about wobbling), and you’re using your hand to flip the board, which is generally easier than using your feet for most beginners. This helps build confidence for landing onto a flipping skateboard, making more difficult moves seem less daunting.


Tailstop Fingerflip Trick Tip

Caspers

Caspers are going to be tough, but you’re basically using the technique to get to heelside rail to land in a different position. The key is making sure you’re balanced on just the tip of the board; never leave a foot on the floor in a casper. These should be just as balanced as a wheelie is. Anything else is a fail, and getting into bad habits now will make them very difficult to break later.

This one will definitely take the longest to learn out of this set, but it’s worth persevering with.


Casper Featured Image

Becoming Competent

At this point, you should hopefully be feeling relatively comfortable manipulating your board in different ways, and your confidence should have increased a lot since you first got on a board. As such, it’s now time to get started on things which might have seemed impossible when you first started down this path, but trust us on this: you’ll have the skills now to tackle these tricks.

Also, if you haven’t already got onto a dedicated freestyle skateboard by now, it’s good time to consider making the switch. If you’re not sure where to buy a setup, our listing of freestyle retailers should help you find an online shop who can help you out2.

G-Turn Featured Image

G-turns

Notice the numbers on the trick tips have jumped up a long way now; G-turns tend to come quite late for most people. My suggestion is to get started on them early. Why? Because they’re going to take time to learn. Like all wheelies, this isn’t something you’re going to land badly within half an hour and get an instant endorphin rush from. This is a long-term time investment which will pay off stylistically and teach you a lot about control. Don’t expect to do a long, sweeping G-turn straight away, but get started on it now and you’ll reap the benefits later on.

Frontside Shuvit Featured Image

Frontside Shuvit

The tailstop fingerflip should have acclimatised you to landing on a moving board, so now you’re going to do that rolling. Shuvits are a little bit more forgiving than kickflips and the like; you’re far less likely to accidentally land on the side of the board and fall over. Providing you didn’t stop practicing your endovers, this should feel relatively natural – if a bit scary at first. Try not to overthink it; you’re well-prepared for this now.

50-50 Featured Image

50-50s

Assuming you’re following the guide and have already learned to go to rail and do a basic casper, this is the last major element in stationary freestyle you’re missing. The 50-50 is a staple element of most freestyle combinations, and at this point you should be relatively well-prepared for learning it.

However, like the casper, it’s important to learn this right. Don’t start with a foot on the floor – a bad habit like that is hard to break and will make a big difference later on.


The Missing Pieces

At this point you should have picked up a lot of key skills which will serve you well on your (hopefully long) journey into freestyle skateboarding, but you’re still missing a couple of key components. Unfortunately, these are some of the more difficult ones to master. However, if you’ve made it this far, you’ve still got a lot to play around with while these final moves are driving you insane.

Railflips

The railflip is something that most people getting into freestyle want to learn, especially if they’ve come from a street skating background. As another common component of stationary combinations, this is something you’ll need to learn before too long, as it opens the door to a lot of different tricks from rail.

We’re recommending this a lot later than you might expect because not only is this an unstable starting position, but the flip can be quite unpredictable at first. It’ll take some time to get over that, but don’t worry – that’s totally normal.


Railflip Featured Image

Kickflip

In freestyle, we still have the original kickflip – the one which doesn’t require an ollie – and there are a lot of tricks starting from this one little flip trick, so it’s an important building block to pick up early on. Getting to grips with it can feel a little alien, which is why it comes far later in “Freestyle Skateboarding 101” than it does in the giant trick repository, but don’t neglect it. No matter what style of freestyle – stationary, rolling, dance-based – you end up doing, there’s a lot you can do with the kickflip.


Kickflip Trick Tip

No Handed 50-50s

Now we’re really into difficult territory. Even if a 50-50 is relatively easy for you at this point, doing it without your hands will feel like a difficult and frustrating experience for quite a while. If you didn’t take our advice about getting a dedicated freestyle board earlier on, this is definitely the point where you’re going to wish you had. But persevere – there’s a reason this is one of the most iconic freestyle tricks, and they never stop feeling satisfying. Landing one of these for the first time is quite an accomplishment, so consider that your final exam on this “course”.


No Handed 50-50 / Truckstand Featured Image

Finding Your Own Path

Having made it through this beginner’s guide to freestyle skateboarding, you might have questioned the choices of tricks, or even the order in which they were presented to you. After all, where was the guide on getting into toeside rail? And why on earth would people learn to casper instead of finding something fun to do from heelside rail at that point – you know, something like the railflip?

Well, there is method to the madness. Each block of three tricks introduces a new mechanism, a new skill or technique, while building on something introduced in the previous block. I tend to think of freestyle as if I was building a house; everyone wants the big flashy mansion (or maybe the cute country cottage), but you have to get there gradually, one brick at a time, and there are multiple components involved in the final building. Unfortunately, we can’t hire metaphorical plumbers, electricians or plasterers to take over mid-way through a competition run, so we have to make sure we have a competent understanding of all the different elements involved.

How that (painfully strained) metaphor translates to freestyle is simple: almost every trick past this point is a combination of skills you’ve learned from the twelve tricks on this page3. You can almost view it as a maths equation or chemical formula, where each trick was broken down to the core components which lead up to it:

180 Kickflip = kickflip + backside shuvit

Backside shuvit = frontside shuvit + backside endover

Once you understand that, the rest of the tricktips – and by extension, the rest of freestyle skateboarding – is pretty much open to you. In every post on this site, there’ll be a link to tricks you need to be able to do before you begin – and if you followed this “course”, you’ll already have the key elements needed for the vast majority of posts. Hell, even tricks we haven’t covered at this point will likely be built from combinations of these 12 tricks!

So what are you waiting for? Go out there, explore, and enjoy it. Hopefully we’ll get a chance to skate together at a freestyle event in the future and you can teach me something new!


Footnotes:

1: This is not a guarantee. Do not hold us to this. Also, don’t worry if it takes you longer than you’d like; everyone learns at different speeds.
2: We recommend Offset Skate Supply in the UK, but we might be a bit biased there.
3: There are some niche exceptions to this rule; impossibles have a starting point all of their own, and handstands don’t even begin on a skateboard. But we still stand behind this basic point.

Need more help?

COMMENTS (2)

  • Jacob Ewen

    30th October 2019 , 6:13 AM / reply

    Had.a little break from trying my freestyle stuff. Keen to learn more though.. I got stuck at no handed 50/50s
    • Tony Gale

      30th October 2019 , 3:17 PM / reply

      Yeah, that's a roadblock for a lot of people. It's a perfect storm of having to stay in contact with the board the whole time, ensuring your balance is perfect andhaving a deck that's working with you and not against you. I remember trying to learn them on street decks without any guidance in my parents' garage. It was one of the most painful and frustrating experiences I've ever had in skateboarding, but it was worth it.

Keep the tips coming

Buy us a coffee!Buy us a coffee! Buy us a coffee! Buy us a coffee!

Subscribe to the Tips

Enter your email below to be notified whenever a new tricktip goes live:

Get the tips via RSS

RSS Feed RSS - Posts