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How To Make Winter Cycling More Fun in 4 Easy Steps

Winter is every cyclists least favorite season, but it doesn’t have to be. Knowing how to make winter cycling more fun has come with many years of experience. I’m talking about those harsh Midwest winters where its so cold your core hurts when you step outside. I’m also talking about those Colorado winters where two feet of snow can drop on you at literally any moment.

All this experience has led me to the four easy steps you must take to make winter cycling more fun. I can make it through most winters with steps one, two and three alone. But, if we have another year with 70 inches of snow I will be making the leap to step four.

4 Steps To Make Winter Cycling More Fun

Step 1: Prepare For Your Ride

Winter cycling is not for the weak spirited. Mother nature can swallow you up and spit you back out licking your wounds. I forgot Chapstick on a windy winter day and my lips were purple by the time my ride was over. I’ve also burned by neck and face by forgetting my sunscreen.

The takeaway here is to properly prepare for your ride. Snow is incredibly bright so you will want to bring sunglasses. If its a sunny winter day you still need to wear sunscreen. Above all, remember your Chapstick. Chapped lips not only make you look funny, but they are incredibly painful.

If you remember all these accessories your winter ride will be a lot more fun. If not, make sure you’ve crossed off everything in step two.

Step 2: Dress Up

Layer up and lower your expectations. In other words, you need to dress appropriately and accept that you won’t be breaking any Personal Records on Strava. You can’t have fun on a bike during winter if you’re busy complaining about how cold it is. This is exactly why I have a winter kit.

My winter cycling kit has two parts. First, I have a drawer dedicated to clothing.

  • Thermal Bib Pants
  • Thermal Cycling Shorts
  • Heavy Duty Winter Glove
  • Light Winter Glove
  • Thermal Skull Cap
  • Merino Wool Neck Gaitor
  • Merino Wool Long Sleeved Jersey
  • Thermal Winter Riding Jacket

The second portion of my winter kit is in a small Tupperware container. I put it in there because if it fits there I know it will fit in my saddle bag.

  • Chapstick
  • Sunscreen
  • Sunglasses (Not in Tupperware)
  • Hand Warmer Packs

If you are wondering where my tools are, I have a hand pump attached to my bottle cage mount. My multitool stays in the saddle bag with my flat kit.

This winter cycling kit was not all acquired on the same day, and cumulatively it is very expensive. I try to buy one item at every bike shop I visit in a new town. Now I just replace what wears out as needed. In other words, it is okay to ease into winter cycling. Maybe a lack of thermal bib pants means you can only ride on days the temperature gets about 40 degrees. Do what you can as you can. If that’s not good enough then you need to…

Step 3: Bring It Indoors

Cycling indoors can be an absolute riot thanks to apps like Zwift and Rouvy. For many years I simply braved the cold but as I get older and appreciate being a bit more comfortable a trainer was the next logical step.

(Read: Wahoo KICKR Smart Trainer Review)

I now have the full Wahoo KICKR Ecosystem so I get the same feel as riding outdoors, but in a temperature controlled setting with far less risk of injury.

Smart Trainers and cycling apps also allow you to maintain the social aspect of riding a bike. You can ride with friends and family on Zwift. You can give each other Kudos on Strava, and so much more.

Step 4: Upgrade Your Bike

Get a fat bike. That is the only bike I don’t have in my garage currently. I would love a Trek Farley or Specialized Fatboy. If Jack Frost comes to visit and my winter kit can’t keep me feeling comfortable outdoors, and I am burned out on the trainer, then and only then will I muster up the courage to ask my wife if I can buy another bike.

It is something I think about every year. I have a couple local bike shops I frequent often and they both usually have one or two fat bikes in stock. I tell myself I will let some other customer have that one because I can always ride the bikes I’ve already got. One of these days that may change, but for now steps one through three give me everything I need to make winter cycling as much fun as possible.

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