How To Ride A Penny Board — A Beginner’s Guide

Skateboarding has never really gone out of style. And with pop culture and fashion harking back to all things ‘90s and 2000s, when skateboarding and skate style became officially mainstream, the culture is once again booming. The popularity of skateboarding in the past couple of years might be due to a combo of factors: The lockdown led many to re-embrace outdoor activities, the Tokyo Summer Olympics in 2021 showcased pro skating on a global scale, and — whether people like it or not — TikTok and Instagram have made the historically West Coast skating aesthetic all the more enviable and aspirational. If you’re just starting out with skating (or want to), you might reach for a penny board thanks to their vast range of colors. Plus, learning how to ride a penny board can be fairly quick to pick up.

One of the most approachable boards in terms of price and design, penny boards are characterized by short and narrow plastic decks, often with a waffle pattern on top. These types of boards have been around since the 1970s, though the name itself was contemporarily popularized by the brand Penny Skateboards, which was founded in Australia by Ben Mackay in 2010. Since then, penny-style boards have since been used as a catchall to describe any small plastic skateboards, and you can find them on the market typically anywhere from $30 to $200 depending on the quality of materials, brand, and design.

Penny boards have historically been popular among students, given that the boards are easy to stick in a backpack, and they’ve remained go-to choices for young people. More recently, there’s been an uptick in interest in penny boards. As just one example, a “rating where I ride my penny board” trend has been popular this year on TikTok under the #pennyboard hashtag, which has over 615 million views.

Over the years, penny boards have sometimes gotten a bad rap from those in the skating community for being less serious — occasionally even with the word “poser” being thrown around — which is mostly chalked up the that fact that penny boards are designed less for parks and tricks, and more for casual transportation and cruising. “The stigma around penny boards comes from the fact that if you are riding one in a skatepark, you probably aren’t going to be trying any tricks and will be in the way of someone who is,” Val Henderson, a New York-based digital creator, tells NYLON. Unfairly, the penny’s price point also comes into play, as its affordable price tag makes it a common entry level choice for those who don’t quite know what they’re doing yet.

That being said, any strange looks or bad attitudes toward riding a penny board should be ignored, as skating at its core is centered on self-expression. “Skating is all about being yourself, though, and if you want to rip the penny board in the park, no one will stop you from doing your thing,” Henderson says. Not to mention, skateboarding should be about having fun, as Pauline Sala, a skater, model, and actress, based in Venice Beach, California, tells NYLON. “I love how free skateboarding makes me feel!” she says. “It took me only a couple days to get comfortable on my board because I fell in love with the sport.”

If you’re looking for the lowdown on how to ride a penny board, as well as what to know before hopping on a one, read on.

Are Penny Boards Good For Beginners?

Lots of people opt for penny boards when they want to begin skating. They can be great starter boards, especially when it comes to learning the fundamentals of skateboarding, such as balance, pushing, turning, and carving. “My first board was a penny board,” Henderson says. “Riding around with my headphones in was a meditative space for me. I was able to explore the surrounding area of my school in Baltimore more than I ever had before and would challenge myself by going down steeper and steeper hills.”

“I’d recommend the penny board to anyone who is thinking about picking up skating in a casual way,” says Henderson. “It’s a convenient and cheap mode of transportation, too! Learning to ride it will improve your balance and challenge you to face your fears (you can get some serious speed on these boards). If you are looking to learn tricks, I’d recommend starting with a traditional skateboard, because there are some differences to riding the two, and buying new setups can be expensive.”

That being said, if you’re unsure what exactly you want out of skating just yet, starting off with a penny-style board can give you skating foundations that are easy to build upon. “I rode this board for a year and half before I got a traditional skateboard to start learning tricks,” Henderson says. “If you watch any ‘How to Ollie’ tutorial on YouTube, the first thing they’ll say is [to] make sure you are comfortable on the board before you attempt the trick (i.e. can turn with control, move with speed, and stop). The penny board gave me this foundation and fast tracked my trick-learning era.”

What To Know Before Getting A Penny Board

If you’re looking to hit up the skate park and learn tricks, the penny board might not be the one for you. “Penny boards are for cruising, not for tricks,” Henderson says. “It’s designed to ride smoother than a traditional skateboard; the trucks are taller and the wheels are bigger and softer. This combo allows you to roll seamlessly over bumps in the road with little to no noise.”

For context, traditional skateboards use hard wheels that have less friction and are better for landing tricks. The loud noise you hear when skateboarders are riding by you on the street is due to these hard wheels, Henderson explains. Penny boards, on the other hand, have soft wheels that absorb the roar, providing a more comfortable (and quiet) ride. “The bigger wheels also allow you to go faster with the same amount of effort — a nice feature for when you’re running errands,” Henderson adds. Need to grab a six pack on your way to the beach or a coffee before class? The penny board is your best friend.

However, those same features that make a penny board smooth to ride also make it harder to do tricks. “Due to the taller trucks and bigger wheels, the board is heavier than a traditional skateboard, making it harder to get good ‘pop,’” Henderson says. “Also, the surface area of the board is usually smaller and does not have the grip tape that traditional boards have.” That isn’t to say that you can’t do any tricks on pennies (plenty of people have), but the way the board is designed makes it better for cruising.

Because of the penny board’s traditional short and narrow design, sometimes those with larger shoe sizes can have a hard time finding a comfortable feet position or sense of balance on the board — though that hasn’t stopped people of all sizes using them (even 6’3” Tony Hawk has been spotted on one). And although the penny board itself is small, there are other penny-style boards out there for all different kinds of skaters, such as the nickel board, a longer penny-style board.

If you do want to spend more time in the park, surfskates — skateboards that replicate the more fluid, back-and-forth motion of surfing and snowboarding — might be a good choice. “If you are interested in skating the park but don’t see yourself hitting kickflips or sending it off the stairs, there is another type of board called a Carver that looks like the penny board deck but has a different set of trucks that swivel,” Henderson says. “You may have heard of this style of skating before as ‘surfskating.’ These boards are super popular in California bowl parks [and] pump tracks and require a lot of hip wiggling to pump for speed.”

Choosing a board that fits you and your interests is probably the most important thing to keep in mind before purchasing a penny board. Sala, for example, gravitates toward Carver boards and surfskates. “I feel like we all have different styles when it comes to skateboarding,” Sala says. “I would recommend thinking about what kind of style of skateboarding you would like to do before buying a board. Do you want to do tricks and skate street (with a trick board), or do you want to be more flowy and feel like you're surfing concrete while skating transition (with a surfskate), or do you just want to cruise from point A to point B (long board, cruiser, penny board)?”

How To Ride A Penny Board

Now down to the actual riding. “Skateboarding is all about having fun, bending your knees, and staying centered,” Sala says. “Fear will stop you from having fun, so try to have as much fun as possible and learn at your own pace!”

Penny boards are smaller and narrower than regular skateboards, so balance can sometimes be trickier to get right away. If you don’t have any experience with skateboards, it can help to start by practicing on the grass or a carpet to get the hang of leaning. Your board won’t really go anywhere on grass or carpet, so you can start to feel what it’s like to lean forward on your toes and backward on your heels, which will end up being the way you control your turns. Once you feel like you understand how to keep your balance, head out to a surface where you can actually gain some movement.

“The process of learning to ride a penny board is similar to learning to ride any board,” Henderson says. “Find some open flat ground without too many obstacles. Definitely don’t start on sidewalks with a lot of people or in the bike lane because you will want room for error. Slowly progress to riding down hills, turning with speed, etc.”

As with any skateboard, you start by figuring out your stance when it comes to pushing and cruising. Whether you lead with your left leg and push with your right (called “regular” stance) or lead with your right leg and push with your left (called “goofy” stance) is totally up to you and whatever feels comfortable. Despite what the names might make you think, neither stance is better than the other; riding regular is just more common.

Once you get the hang of pushing and stopping, you can incorporate turns, as well as pick up your speed. One thing to note about penny boards is that they make much tighter turns than typical skateboards, so you’ll be able to maneuver around things fairly easily once you get control of your movements. From there, you can challenge yourself by gaining more speed and going up and down small hills.

When it comes to learning how to ride any skateboard, trust yourself, but also be patient — not everything can be learned in a day, and making mistakes is all part of the process. “Also, bring a friend!” says Henderson. “I skated alone for a while, but once I got to New York and started meeting the community of skaters here, I progressed much faster. It’s fun to be challenged by your peers and important to surround yourself with people who have similar goals (on and off the board).” Learning around someone who already has a knack for things can be especially helpful, as they can pass on their own tips and tricks — as well as offer moral support if you end up on the ground every once in a while.

All in all, penny boards offer a fun beginner (and budget) friendly way to get into skateboarding. Whether you want one purely for some speedy, smooth transportation or to help build your skating foundations, penny-style skateboards are a great option for those who want to cruise in style.