Winter Riding: How to Dress, What to Expect, and Why It's Worth It 

Winter riding wasn't something I chose. It was a necessity. When you're working in the outdoor industry in Northern Vermont and the snow conditions are inconsistent, you find alternatives to stay outside. For me, that meant fatbiking. What started as a basic need to be outdoors turned into an avid appreciation for cold-weather riding that I still carry with me today. 

Whether you're dealing with sub-zero temps in Vermont or just trying to keep riding through a cold snap in the Southeast, the principles are the same: dress smart, prepare your bike, and understand what you're getting into. Cold is relative. What feels brutal in North Carolina might be mild in Minnesota. But the strategies for staying comfortable and safe don't change much. 

If you've been curious about winter riding but haven't pulled the trigger, or if you've tried it and cut rides short because you weren't prepared, this is for you. 

Why Bother Riding in the Cold? 

Let's be honest. It takes real motivation to get out when it's cold and dark. Starting a ride in the dark, especially when temps are below freezing, requires mental effort. But here's the thing: once you're rolling, it gets easier. The hardest part is always getting out the door. 

The payoff is worth it. Winter trails are quieter. The surfaces are different, sometimes faster, sometimes more technical in unexpected ways. And there's something about finishing a cold ride that makes you feel like you actually earned it. You're not just riding to stay fit or kill time. You're riding because you made the choice to be out there when most people are staying inside. 

What to Expect When You Ride in the Cold 

If you've never ridden in truly cold conditions, here's what's going to surprise you: 

The first few deep breaths hurt. Like, a lot. That cold air hits your lungs and it feels sharp. It mellows out after a few minutes, but don't let it freak you out at the start. 

Everything runs in slow motion. Hydraulic brake fluid, suspension oil, bearings in your hubs, it all gets sluggish when temps drop. Your brakes might feel a little mushy at first. Your suspension might feel like it's got no life. Give everything a few minutes to warm up, and it'll come back. 

Everything feels stiffer. Your tire rubber, your grips, your bar tape, even your saddle. The saddle warms up eventually, but until then, it's like sitting on a block of ice. The rubber of the tires stay firm for the whole ride, which changes how the bike handles, especially if you're used to running lower pressures in warmer weather. 

The sounds are different. Cold surfaces make your tires sound louder, more pronounced. Winter is quieter in general, so every little noise gets amplified. It's actually kind of meditative if you lean into it. 

Temps fluctuate throughout the day. If you're starting early in the morning, it might be 20°F at the trailhead and 40°F by the time you're done. Or if you're riding into the evening, it could drop 15 degrees in an hour. Plan for variability. Don't just dress for the temp at the start of your ride. 

How to Dress for Cold Weather Riding 

This is where most people mess it up. They either dress like they're going skiing (way too warm) or like they're going apple picking (not warm enough). Neither works. 

Here's what I've learned after years of trial and error, including plenty of rides I cut short because I got the layering wrong: 

Start a Little Chilly 

The golden rule: if you're comfortable standing still at the trailhead, you're going to be too warm once you start moving. You want to feel slightly chilly when you roll out. Your body generates a ton of heat once you're into the meat of the ride, and if you overdress, you're going to be soaked in sweat within 20 minutes. Sweat is the enemy when it’s cold out. 

The Layering System That Actually Works 

Base Layer: A short sleeve wool shirt works for most cold days. Wool regulates temperature better than synthetic, and it doesn't stink after one ride. On the coldest days, 10°F or below, throw on a long sleeve baselayer underneath. 

Mid Layer: A flannel or a light insulating layer. Something that traps heat but breathes. If it's windy or brutally cold, a windproof light jacket is mandatory. XC skiers and cold-weather outdoor brands figured this out long before cycling companies started making winter-specific gear, so don't sleep on non-cycling options. 

Bottom Half: Normal riding pants work most of the time. If it's really cold, long underwear underneath makes a huge difference. On the coldest days, windproof underwear can go a long way in keeping your core warmer longer. I rarely wear full-on insulated winter riding pants unless it's single digits or I know I'm going to be out for hours.  

Hands and Feet: This is where people suffer the most. Get proper winter cycling gloves, thick enough backing to keep your hands warm, but dexterous enough to still operate your brake and shift levers. If your gloves are too thick, they’ll feel bulky, creating a more cumbersome feel for your shift and brake levers. This is somewhere in this ecosystem that I highly recommend cycling-specific gloves, like Cognative MTB’s ‘Cold Weather Tech’ gloves. Grab a pair of nice wool socks or your favorite ski socks; they’re designed to keep your feet warm even when a little sweaty. Don’t sleep on the $1.00 toe warmers you can buy at almost any store during the winter. They can make a huge difference on the coldest days.  

Bar mitts are an option for seriously cold temps. Just imagine you’re putting your hands into an extra large and super insulated sweatshirt pocket.  For trail riding, I don't recommend them unless it's well below 10°F, or your hands just really can't handle the cold. They widen your handlebar width, which gets annoying on tight trails, and the stiff cuffing around the wrist gets in the way during aggressive riding. If you crash with them on, they fill with snow and turn into cold, wet sleeves. I also found that even on the coldest rides, if I was riding hard, I'd overheat and end up shedding them anyway. That said, they might make more sense on a drop bar bike where your body is in a more static position, and you're generating less heat at your extremities. On drop bar bikes, like road and gravel bikes, you’re going at a much higher average speed, so windchill plays a massive factor.  

Winter-specific shoes or shoe covers make a massive difference. Don’t underestimate the value in purpose built equipment if it get’s you out on your bike. Companies like 45North make incredible winter cycling shoes and boots for both flat and clipless for mountain biking. For gravel and road focused riders, your normal riding shoes with insulated shoe covers are usually enough to do the trick. If you suffer in the cold easily, a winter specific road shoe, like the Northwave Celcius shoe, would really do the trick.  Cold feet will end your ride faster than anything else. The shoe covers act as a nice barrier from the wind and are designed to help keep the warmth in.  

Head and Face: A thin beanie or headband under your helmet keeps your ears from freezing. On the coldest days, a neck gaiter or balaclava protects your face and helps warm the air you're breathing in. 

Mountain Biking vs. Gravel/Road 

Mountain bikers generate more body heat because the body is constantly moving, shifting weight, pumping through terrain, and reacting to the trail. Gravel and road riders sit in a more static position and are often riding at a much higher average speed over the course of the entire ride, which will make it feel much colder. If you're road or gravel riding in the cold, you're likely going to need an extra layer compared to what you'd wear on a mountain bike in the same temps. 

Prepping Your Bike for Cold Weather 

Your bike doesn't care that it's cold. It'll still ride. But a few adjustments make a big difference in how it performs. 

Tire Pressure: I drop my tire pressure by a pound or so in colder temps. The rubber gets harder when it's cold, so reducing pressure helps maintain traction and compliance. On a fatbike, this is even more important. Those big tires need enough give to grip frozen or packed surfaces. (Pro tip: over-inflate your tires inside where it is warm, then let your bike sit outside for upwards of 20 minutes to let it acclimate to the cold. From there, check your tire pressure, as the pressure can drop significantly once outside.) 

Controls: If you're wearing thicker gloves, adjust your brake and shift lever reach so you can still operate them comfortably. This is easy to overlook, but it's the difference between smooth, confident riding and fumbling around with levers that pinch onto thicker gloves or get in the way of all the extra material. 

Suspension (MTB): Cold air means thicker oil, which makes your suspension feel sluggish. Speed up your rebound by a click or two on both your fork and shock. If you're running a rear shock with tool-free adjustments, like our Kitsuma, it takes about 10 seconds to dial this in. When temps warm back up, don't forget to set it back. 

Drivetrain and Brakes: Give everything a few minutes to warm up. Your hydraulic brakes might feel a little soft at first. Your chain might feel a little stiff. Once you're moving and everything “warms up” performance will return. 

Winter Fatbiking: A Different Beast 

If you've never ridden a fatbike in winter, it's hard to describe. Many trail networks in colder climates will snowshoe, shovel-pack, or even machine-groom existing bike trails to create a firm riding surface. Some of us would take summer flow trails and build snow jumps, salting the lips and landings to firm them up. 

Here's the thing: any root or rock that was gnarly in the summer gets smoothed out by the packed snow. In some cases, trails ride as fast, or faster, in the winter than they do in the summer. It's a completely different experience, and it's one of the most fun ways to ride a bike when conditions are right. 

Cold weather riding in the Southeast is different. We don't face the same sub-zero temps or deep snow, but the principles still apply. Whether it's 10°F in Vermont or 30°F in North Carolina, if you're prepared and dressed right, the ride is still worth it. 

Finding What Works for You 

The reality is there's no one-size-fits-all approach to winter riding. What works for me might not work for you. The key is experimenting. Try different layering systems, adjust your bike setup, and figure out what keeps you out longer and more comfortably. 

And if you get it wrong the first time? Cut the ride short, go home, and adjust for next time. That's how you learn. I've done it more times than I can count. 

Winter riding isn't for everyone, but if you're motivated enough to get out there, the experience is worth it. The trails are quieter. The conditions are different. And when you finish a cold ride, you feel like you actually earned it. 

So, dress smart, prep your bike, and get out there. The cold isn't going anywhere. You might as well make the most of it. Feel free to take what I have written here and apply it to your winter riding. Or don’t, These are just words written by a guy who doesn’t wear cycling gloves even in the winter (unless it’s below 20°F.) We’ll see you out there. 

Need help dialing in your bike for winter? Hit us up at support@canecreek.com or call (828) 641-9560. We've been riding in all conditions for a long time, and we're always happy to talk through what'll work best for your setup.