How Can Biking Stay Joyful in the Midst of Winter?

Lynda Lopez
Lynda Lopez

I never considered myself a hard-core winter bike commuter before last year. I still don’t know if I can call myself that, but I’m getting there. Last year I was working at the Brighton Park Neighborhood Council on Chicago’s Southwest Side and living a few miles away in the Little Village eighborhood. That might not seem like it would lend itself to a challenging commute, but what I’ve learned is that the intensity and strenuous nature of your commute depends on the your environment and how used you are to the elements on a bike.

I don’t come from a community of cyclists who exchange tips about winter riding. I’ve slowly built my knowledge by jumping into it and asking questions as I go. I dare say this is how many winter commuters tackle the challenge. They don’t have fancy gear, but are trying to figure out how to keep their bikes going in the winter. This seems to be the case with the older Latinx folks I see navigating the streets of Little Village and the Pilsen community on two wheels every day.

I first started riding in the winter in 2011, when I was living in the Hyde Park neighborhood and biking to classes at the University of Chicago, but it was a short distance on fairly well-maintained roads, so it wasn’t too much of a struggle. Last year, while trying to commute a longer distance to work, I learned all the layers (pun-intended) of biking in the winter.

First, I had to get used to the seeming contradiction of overheating in the cold. It can be freezing outside, but depending on the amount and kind of layers you wear, it’s all too easy to end up in an uncomfortable sweat. Therefore, I learned to wear fewer layers  for cycling (finding the perfect balance is still a work in progress, though.)

Lynda riding a CTA elevator during a winter bike-and-ride trip.
Lynda riding a CTA elevator during a cold-weather bike-and-ride trip. Photo: Michelle Contreras

Second, I learned that I highly dislike the wind in my face. Since I was riding in the street at a fairly high-speed down California Avenue, the wind chilled me in a way I wasn’t used to, even though I’m a lifelong Chicagoan. I eventually invested in a balaclava, a face mask that fits under a bike helmet. This helped ease the pain in my face.

Third, I discovered how messy my clothes could get when the rain or melting snow would splash on my back. I eventually learned about the benefits of fenders, which solved that problem.

Winter bike commuting is also about trusting that you will feel comfortable after a bit of initial pain. In my experience, the first few minutes of a ride are never quite enjoyable. It’s only after you build some speed that you also start to warm up. On the plus side, it’s easier to stay warm on a bike than it is while walking in the cold, let alone waiting at a bus stop or ‘L’ train platform.

I do find it harder to endure cold-weather bike commuting on long trips. So if I need to travel many miles, I typically opt for public transit, sometimes taking my bike with me on the CTA to cover the first and last portions of my trip.

This year I’ve kept biking in the cold at least a few times a week, although the recent snow and icy temperatures made me less eager to do so. I did finally invest in a windbreaker on Black Friday, which will hopefully make it easier to maintain a decent warmth as temperatures dip. I can’t say I’m hardcore about gear, but I opt for as much comfort as possible (that stuff is also expensive.) I also don’t want to have to alter my fashion based on riding. I wear jeans and I’m still learning what a good jacket on a bike means.

I’ve learned, however, that I am very much a pleasure bike commuter. I bike partly for convenience, but also for the joy component. My question every year is, “How can biking stay joyful in the midst of winter?”

The last few weeks have been a bit tricky. I’m not a fan of biking in snow, partly because it hinders the vision of drivers and the roads generally just feel more treacherous. I can handle rain a bit more, but it still makes me nervous. Chicago has been both rainy and snowy in the last week, which has added the added difficulty of icy streets and sidewalks. I have definitely fallen while taking my bike out of my apartment and slipping on icy sidewalks before. All of these small things can be major obstacles for people who want to keep biking through the winter.

I’m still learning and have invested in some equipment and clothing to facilitate this process. If you want to keep riding in the winter, I think it’s necessary to decide what kind of rider you want to be. This year, I think I determined I want to be able to keep riding my bike when I want to run local errands and when I want to go somewhere within a few miles and don’t want to take the bus. I’m not as invested in long-distance riding in the cold, and my work and life doesn’t require me to do that on a regular basis. In those cases, I’m fine with public transit.

My goal for this winter is learn more about (intentionally) biking in rain and/or moderate snow. I still don’t have a rain jacket. Has anyone invented an umbrella for my bike yet? Let me know. (Yes! — Ed.)

donate button
Did you appreciate this post? Consider making a donation through our PublicGood site.

  • BlueFairlane

    Here’s a question for the streetspeople in general that’s perhaps inappropriate for this post, but I’ve never been a big gear guy, and I don’t want to join Chainlink just for this. Say you used to bike a lot in winter, but you’ve got breathing issues that makes that difficult in cold weather, so you want one of those indoor trainer things to go with your Trek Verve cruiser bike. Will just any indoor trainer off Amazon do, or do you have to spring for Trek gear?

  • johnaustingreenfield

    Yep, that’s a Chainlink question — none of us Streetsbloggers are experts on indoor biking.

  • planetshwoop

    Great piece!

    I have two critical must haves: gloves/mittens and long underwear. The gloves can be cheapish leathery ones from the hardware store so I don’t get upset if they get lost. And long underwear for layering my legs. Again, cheapish from Target is ok as long as it’s not cotton.

    One tip to deal with the “umbrella” question is to put duct tape on your helmet over the vents. It keeps things dry for little money.

    Great article. Winter biking is an acquired taste but you did a great job covering it.

  • Jim Green

    I’m still looking for a solution to frozen toes when the temps fall below 25 degrees or so…. After half an hour of biking, this is my main problem.

  • Random_Jerk

    I really don’t know why people make such a big deal about winter riding. Yes, it’s cold outside but it’s equally cold when you walk – or worse – wait at the bus/train stop.
    I would rather be moving. In 3 minutes I’m usually warm enough to unzip my jacket. Past winters were relatively snow free, so most of the bike lanes and roads were clean and safe to ride. No studded tires necessary. The only winter “gear” I have is face mask and really warm gloves. I hate long johns :) . My bike commute is around 20 min. Even in the extreme cold it beats 50 min of walking, or nonsense CTA bus that with waiting/walking takes longer than a plain walk… Not to mention being stuck in the car in the rush hour…

  • David P.

    Great piece, Lynda. I made an intentional decision to be a year-round-for-everything rider when I moved to Chicago ten years ago, but even then it took me a couple of years to acclimate to riding in *everything*. I had the clothing I needed, and decided the only thing stopping me was my attitude. Figuring out a clothing regime that works for you is always an iterative learning process that takes some time. It’s perfectly possible to ride comfortably in winter in normal clothes, particularly if you’re not exerting yourself too hard. A windbreaker is very useful to have but a heavy wool winter coat like the one in the photo works perfectly well for many conditions with good layering and venting. The one exception you may want to think about when it comes to maintaining your normal wardrobe is the jeans – if it’s dry they should be fine, with tights underneath if needed, but if it’s cold and wet, jeans are miserable.

  • johnaustingreenfield

    Wiggle room for your toes is key. I’m a fan of Blundstone Australian farmers boots for wet or cold riding, or anytime except the dead of summer. They’re not particularly expensive, but they’re made of thick, solid pieces of leather that keep rain out in all but the heaviest downpours, and they’ve got a roomy toe box for blood circulation. They’re not particularly heavy, they look reasonably nice, especially the “chisel-toe” models, and they’re slip-ons, so they’re easy to kick off when you get home. (End unpaid endorsement.)

    For riding in really cold weather or on messy, snowy streets, I switch to lightweight, insulated hiking boots, these ones, I think:

    For budget alternatives, check out thrift stores and army-navy shops for warm, water-resistant footwear.

    For socks, remember that cotton is not great for winter biking because it gets cold and clammy when it gets wet. Army-navy stores are good places to find cheap rag wool socks, and fancier polypropylene and merino wool socks from outdoor gear stores are very nice.

    If I’m dealing with really wet and/or cold conditions, I’ll wear SealSkins Gore-tex waterproof socks over my regular socks. A cheap alternative is plastic bags over your socks and under your shoes, which was my standby back when I was a messenger.

    If you’re wearing bike shoes that clip into the pedals, the neoprene over-booties that they sell at bike shops work well, and there are also some good winter roadie shoes on the market (not that I’m an expert on roadie gear) — Lake used to make some good ones.

    More tips on how to dress for winter cycling, including some low-cost options, here:

  • Anne A

    My answer: fleece balaclava. I have asthma, so breathing in cold air is rougher than it used to be.Breathing through a fleece balaclava is a lot easier on the lungs. As a shortcut, breathing through a fleece scarf is also effective. The key is having a breathable layer between your face and the cold air.

    I don’t have any knowledge specific to your trainer question.

  • outerloop

    Cheap but effective foot layering for very cold temps:
    Base- thin sock or sock liner. 2nd layer- plastic bag. Outer layer- thicker insulating sock. With this combo, most reasonable shoes or boots work fine.
    If the plastic isn’t sandwiched between layers of cloth it’s more likely to tear.

  • rohmen

    Does your Trek have a quick release rear hub/wheel (or the ability to take a traditional quick release skewer for the hub)? If so, the majority of trainers likely would work, though it may depend some on what width tires you’re using on your cruiser as well. I’ve never tried anything bigger than a 700 x 25 on mine, and I’d imagine they do have a width limit if you;’re running something really wide.

    If you have a rear hub that uses axle nuts, I think you can start running into issues on some trainers. I recall a friend having to order an adapter for a Cycleops trainer when he had to fit axle nuts vs. quick release.

    Honestly, given the somewhat nontraditional set-up you’d be doing, I’d maybe hit an REI and ask. They should know and sell all the major brands.

  • siouxgeonz

    Okay, will try this one more time.
    I find with actual Gore-Tex jacket (given to me when somebody retired; now I understand why people spend the $$$) … riding in the rain is *nice.* (Not when it’s blinding or flooding or slimy, of course, but cruising through a gentle drizzle I can feel the pitter patter on me … but I’m not getting wet, and I’m warm and dry in my flexible armor…)
    When it’s sub-20 Fahrenheit I will try to include five minutes inside doing jumping jacks or hopping on the trainer … then I get to skip the uncomfortable part.

  • siouxgeonz

    (I have been known to remind people that lots of people pay big bucks to go out and ski … if you have the gear, it’s comfy.)

  • siouxgeonz

    Are you clipping in? Metal on metal… (Cold toes aren’t an issue for me and I’m a socks and sneakers person, but it’s also just not my Achilles Heel… my ears are my Thing That Must Be Covered!)

  • siouxgeonz

    There are totally different kinds of trainers. You will want to do some actual research. What will keep you from actually using it? Boredom ? The thing being poor design (so it doesn’t feel anything like actually riding)? Cheap ones are pretty nasty.

  • Mcass777

    Maybe the best responses to an article ever posted on this site!

  • Tom

    Big fan of switching to Divvy bikes in the winter. Slower than my normal bike but tires do remarkably well in the snow and you can hop off easily if it slips on an icy patch. Brakes also work well with mittens, which I find are the only way to keep my fingers warm.

    Only hard part is if the docks are covered in ice.

  • rwy

    I find that having something over my nose makes my glasses fog up.

  • Paul

    I recently got an inexpensive gator. Unplanned purchase. Now won’t ride without it. Can’t breath through it but keep it up to lower lip. Below 25-30° use balaclava depending on wind and length of ride. Also believe you must wear bright colors, especially in winter to be seen

  • johnaustingreenfield

    Smart purchase — all winter cyclists should consider buying an animal mascot to cuddle with on the ride. However, I would recommend using a warm-blooded one — they generate more body heat. (Sorry, couldn’t help myself.)

  • ridonrides

    I agree with so much Lynda has said. Biking in winter isn’t “fun” but it’s not as miserable as one would think. You get used to the blast of cold wind (I don’t use a facemask, it fogs up my glasses). Yes it does hurt your face, but only for a little bit. I wear puffy down ski mittens not those lobster ones. Winter hiking socks are a godsend. Yes, all these things cost money even if they’re not bike-specific. I feel lucky that I have them and they’ve lasted me through 8 years of winter biking.

  • Anne A

    I have my nose covered while I’m rolling (no fog on the glasses) and uncover it when I’m waiting at a stoplight or otherwise paused.

  • Anne A

    Finding a combination of clothing and other gear that works for you makes all the difference in having good winter rides. I like hiking books to keep my feet warm. Riding in snow can be a wonderfully peaceful experience.

  • Courtney

    I am currently wearing some cheap cotton gloves from Target. I sometimes opt to wait at the bus stop because I can tuck my hands away in my pockets versus having wind hit them while I’m on the bike. Can’t wait for my new gloves to get here on Friday!
    I totally get your points though. I opt for a 2-3 minute Divvy ride to the train station vs a 10 minute walk for the same reason: I would much rather be moving faster/quicker and generating heat.

  • I’m gettin’ there.

  • TonyAB

    Agreed, though their tires could have a *little* more tread … many times the back wheel loses grip on slushy stuff. But knowing it’s easy (and safe-ish) to hop off if you have to is nice.

  • LMrides

    In this weather I’m using bar mitts and am comfortable even without gloves! I, too, like to ride in whatever I would normally wear, on or off a bike, so I hooked up my bike with a front basket for my purse and can even ride in chunky heels on the way to work. I like being able to bike winter and still walk into the office looking more or less profesh. Also, Lynda, I’ve been interested in a bike poncho/rain cape for a while but have never taken that leap – maybe something to look in to?

  • johnaustingreenfield

    No joke, at a party this weekend I woman I know who has recently gotten into riding with bar mitts, also known as pogies, brought up the idea of putting on a meet-up ride for fans of the gear, either the Pogie Pierogi Ride to a Polish restaurant or the Bar Mitts-vah ride to a deli.

  • Kenath Sponsel

    If you’re riding in bike shoes (with clip-in pedals) there are tons of options for shoe covers that will keep you dry and toasty.
    If you’re in regular street shoes/boots, you can try motorcycle boot covers. They look a bit goofy, but it’ll keep your feet dry in the worst weather.

  • e_ben

    I know this grosses some people out but i put a thin layer of vaseline on my face when it gets down into the teens/single digits. helps a lot with wind burn. plus when i get to where I am going, it feels so good to have a warm wet rag or paper towel to help take of the vaseline. works for winter running too.

  • Natalie

    You could always wear a thin, but warm beanie under your helmet to stay warm. I LOVE this beanie! And the company is based in CHICAGO and makes there apparel in the USA. I’m sure there are other thin helmet liners, but this one was featured/recommended by Outside Magazine in there 2018 Winter Buyer’s Guide. Feels good to support up and coming Chicago companies too!


Why Do Women Use Their Divvy Memberships Less Than Men?

Divvy’s data release last month raised as many questions as it answered about bike-share use in Chicago. Chicago Spectrum was the first to point out that there’s a large gap between male and female Divvy members. Women make up 31 percent of the membership, but the trip data showed that women made only 21 percent […]