How To Win At Winter Riding


By Kelly O’Brien

A couple years ago, I got off the Metra from the Northwest suburbs, excited to give my new Divvy membership a go in the snow. I couldn’t wait for this blustery November day to mark my first winter bike commute in the city. I approached a Divvy dock outside the Ogilvie station, key fob in my double-gloved hand, and watched as a gust of wind lifted the entire fleet into the air. As the bikes bobbed up and down, I let my hardcore commuting dreams blow down Madison while I hopped on the next bus. “The Windy City is no place for winter riding,” I thought, letting the wintry wind win.

A year later, I finished in the top three of the Active Trans Winter Bike Challenge, so WHO’S WINNING NOW, WIND????? I went from being too wimpy to Divvy two miles from the Metra, to skipping the train altogether and riding 30 miles all the way to work every day. No matter what distance you want to ride or what conditions you want to ride in, you can do it. Put the Ventra card down and bundle up because you’re going to ride this winter, and here’ how…


Wearing the right winter gear is crucial in kicking fear to the snow-covered curb. There’s no such thing as bad weather, only bad clothing decisions. So let’s make good decisions!

  • Gloves: Your hands will likely be the first part of your body to get cold because they’re completely exposed to the wind atop your handlebars, so gloves are super important. When temps hover in the 40s, merino wool long finger gloves will get the job done. But when the wind chill starts to become a factor, your fingers will require something more windproof. For the actually freezing days, learn to love lobster gloves. Though they inhibit your ability to shift, they will keep you warmest. As a last resort, wear latex gloves underneath for more wind and water protection.

  • Headwear: Merino wool caps are key. Not only will a cap’s stiff brim keep precipitation out of your eyes, but its ear covers will limit wind noise and provide slight warmth in the 40s. For 20 and below, break out the balaclava a.k.a. ski mask. No matter what you put on your noggin, be sure your helmet fits properly with all those layers underneath. Some helmets like the Giro Sutton have winter kits available. There are also winter-specific helmets if you want to go all-in.

  • Feet: Wool socks will be your savior. They’re the warmest option, and even when they get wet, they will retain heat. For extra protection from the elements, layer your cycling shoes with toe covers or shoe covers. If you want to recreationally ride tons of miles, clipless winter shoes are a thing. But for a short commute, regular winter boots with flat pedals will work just fine. The Stolen Thermalite pedals give a big, grippy platform for a small price. When it’s really cold and wet, your feet are bound to get cold and wet no matter what you do unfortunately. There are plenty of little tips you can try: plastic bags over your socks, wrap your feet in tin foil like lil baked potatoes, stuff newspaper in the front of your shoes, etc. I’ve tried them all. They all work to a small extent. Typically, the first 15 miles are doable no matter the conditions. Beyond that, numbness sets in. That’s why I would plan my routes so that coffee shops were nearby in case I needed to warm my feet and my soul.

  • Eyes: You know how your eyes start crying when it’s cold even when you’re loving winter riding and you’re so happy?? Yeah, me too. You have to wear some kind of eye protection to stay clear of the tears. Clear glasses are good, but goggles are better for bitter cold. Be mindful of the annoying fogging up of most glasses. There are anti-fog options as well as sprays. Or be like me and just spit in your glasses. I’m gross. But guess what...winter is gross!

  • Torso: In case you haven’t gotten the memo yet, merino wool is the way to go for all things winter riding. Get yourself a merino base layer and STAY AWAY FROM THE COTTON (unless you enjoy sweating profusely and then freezing when your sweat becomes cold). For your outer layer, a windproof and waterproof jacket is 100-percent necessary. The wind is what will really cut through you, so you need to block that with all your might.

  • Legs: When snow and sleet are imminent, waterproof rain pants are your best bet. The Endura Gridlock pants are THE BEST. I spent a lot of miles in the same snow pants I wore sledding as a child and let me tell you, it was awful. Puffy snow pants do not provide much mobility for pedaling purposes, and they will inevitably get caught in your chain. Get some cycling specific rain pants and save yourself from the troubles I may or may not have experienced. They slide right over whatever pants you want to wear for work. Thermal tights underneath will keep you toasty on the coldest and wettest days.

  • Maintenance: I’ll tell you a little story about my winter maintenance last year. Here’s the story: I did nothing. NOTHING. My bike literally creaked so much come spring that I thought I heard it say, “I HATE YOU, KELLY!!!” Thus, I had to replace everything: chain, front chainring, cassette, the list goes on and on. Please let this be a cautionary tale. Do these simple maintenance tasks and avoid having to replace ALL the parts:

    • Wipe down your bike after riding through sludge, snow, and all winter’s wonderful elements.

    • Clean and lube chain more regularly due to the corrosiveness of salt. Use GOOD chain lube like ProGold Extreme.

    • Fenders help keep you and your bike clean and dry, so consider adding them to your bike if possible. If you don’t have fender mounts, it’s ok! There are clip-on options. Speaking of fenders, let’s touch on some other essential accessories for your bike this winter...



  • Lights: Visibility is always important, but it’s especially crucial in the winter months when it gets darker much earlier. For the front light, you will need at least 100 lumens to illuminate the road in front of you. Anything less will allow others to see you, but you won’t see much at all. No matter the amount of lumens you choose, go with USB rechargeable lights because batteries drain quickly in cold temps. Keep a charging cable at work and home so you never have to worry about losing power.

  • Tires: Just like cars have snow tires, so do bikes. But you can make regular tires work too. Start by running a lower tire pressure to get more traction on slippery roads. Just be conscious of the higher risk of pinch flats when you’re tires are lower than usual. You can get studded or snow tires, but I prefer a more versatile all-condition cyclocross tire like the Clement MXP. Whichever style of tire you prefer, you will want to brush up on your winter bike handling skills.

  • Handling: Firstly, don’t make sudden movements! When approaching ice, coast over it. Do not pedal hard or brake suddenly. Hold your line and relax your body. If you tense up, you’ll be much more like to take the spill you’re dreading so much. The same goes for when you cross bridges. The bridge grates get real slippery and ice over before the roads. Breathe and cross with caution. In regards to turning, use only your handlebars, not your hips or shoulders. Stay calm and you’ll stay upright.

Now you’re all set to beat the bad weather with good clothing and accessory choices and better maintenance and handling skills. Moral of the story: As long as you equip yourself and your bike properly, you can (and will) ride this winter. After all, you can’t spell “winter” without “win.” And you can’t say “bicycle” without “icicle.”