Freestyling Skateboarding for the Freestyle Contest Season

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This month, I’ve managed to rope your favourite Urban Surfer blogger Ed Bread (Insta: @breadskates) into trying some freestyle skateboarding tricks with myself, Anthony Simm (Insta: @anthonysimmskate).

I’ve known Ed for a few years now, since returning to skateboarding after a 12 year break. Both of us spend a lot of time skating at Dynamix in Gateshead, UK. We both have our own styles, as you may well know by now, Ed is a flowing, cruising skater with a hint of the old-school with his signature sweeper tricks.

My own skateboarding is based off of the original flatland skateboarding made popular in 70s/80s and 90 – freestyle skateboarding. This style of skateboarding is still going strong today with Instagram and Youtube being a popular platform for sharing videos of freestyle tricks – nearly every skateboarder has a freestyle tricks in their pocket, probably without knowing it.

So when Ed and I had a skate last weekend, we thought it would be a fun idea for a blog and video, getting someone new to freestyle to learn a few of the core tricks and basics of freestyle, sharing all the bails and steps on the way to learning them.

Starting the session, we started with the basics – getting into Rail.

Rail is where you are stood on the side of your board, with the edge of your deck on the floor, standing on the side of your wheels. You can do this either toeside or heelside, depending on which way the grip faces (heelside is grip facing your heel). Ed managed this no problem at all! Most people manage this one relatively quickly.

See this tutorial here for another way of getting into rail than the way shown in the video: https://freestyletricktips.com/rail/heelside-rail/

Throughout the video, we tried several tricks, such as nose caspers, tailstop fingerflips, railwhipbacks, and more. After a few attempts, Ed managed his own versions of these tricks – we might make a freestyler of him yet!

However, towards the end, Ed got his own back – he put me to the test with his own oddball tricks.

Starting with a Russian boneless/jimmy whip combination, this not only confused the hell out of me, but I looked like a complete plum copying it. Ed was pretty amused by this and started the next trick with a fakie ‘walk-the-dog’ sequence. I’m going to make a confession here – although this is pretty much one of the basics of freestyle, I’ve never been very good at them – as you can see at my attempt. I’ve always done mine slightly differently by working in a few extra movements. However, it’s given me something to work on!

After a good session, we both came away with a few new tricks and appreciation for the techniques required in each little ‘niche’ of skateboarding.


Now, freestyle skateboarding is going through a modern day revival and is getting a lot of exposure online. I recently wrote a blog post on freestyle skateboarding for Urban Surfer about whether Freestyle skateboarding was dead or not – at the time I failed to mention the huge amount of work put in behind the scenes by people like Stefan Lillis Akesson and many others who kept the scene alive during the quieter times, bringing it back to life to what it is today!

There are many competitions for freestyle with more and more being organised each year, often in conjunction with other skateboarding contests or events.

One of the first of the year was Spring Sessions at 4motion Skatepark in Darlington. This event I organised myself, creating a skateboard-only session for the full day, with 2 competitions – Street and Freestyle. Street was sponsored by Urban Surfer, Native Skatestore and Legacy Skatestore. The freestyle contest was sponsored by Mode Skateboards, Never Enough Streetstore and Moonshine Skateboards. I want to take the opportunity to thank all the sponsors for their prize donations and making the event a great success.

The freestyle competition was the first freestyle contest in the north of England for years and went down a storm. I placed 4th overall which I was really pleased with! Each rider was given 2x 2 minute runs, which were judged out of 100 points total with up to 25 for each category, in Style, Consistency, Variation and Difficulty.

My first run – I’m going to freely admit this was kind of a write off. Obviously the initial nerves of the first run, what to do, what order, what combos etc was in my mind and after missing a trick early on, this got into my head and I missed a few tricks in a row after this. After getting a few tricks back on point, I managed to salvage the run somewhat.

My second run, I was a lot more relaxed. Feeling the flow a little more with my choice of music, I got into a bit of a rhythm and skated pretty well. Despite a few missed tricks, I put together a much better run than my first which pulled my points up. It could have been better if I hadn’t run out of steam towards the end of the run, bailing my usual go-to kickflip to rail combo (I couldn’t even get the kickflip properly and I just gave up!)

To see all the freestyle runs: Spring Sessions – Freestyle Runs Playlist

I’ve got my sights set on the European championships this July 7th 2019 in Paderborn – this is one of the biggest freestyle contests in Europe and bring competitors from all across the globe. I’ll be entering the amateur division and competing against some of the best in the world – it’s going to be a hell of a test of my nerves and skating ability but I’m up for it – it should be a good laugh with plenty shenanigan filled nights on the way, heading across in a convoy with not just my other half, but with the best freestyle skaters the UK has to offer.

Roll on July 7th.

Anthony Simm – Trick Drilling for Freestyle Contest Season



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