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Anyone commute in the winter? Biggest challenge? Necessary gear? Bike maintenance issues?

I am determined to do some commuting this winter.

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Yes. The cold and wind are probably the biggest challenges- not necessarily just for the riding, but partly for the motivation to get out there and do it. You have to dress smart- wool is a great material, and you'll need good gloves, shoes, and a windproof layer. You'll have to get the hang of what works for you in terms of how much clothing to wear. Best to dress in layers so you can add or remove... Ride carefully on potentially ice and snow covered roads, but the fortunate thing about the city is that they do a pretty good job of keeping the roads clear in the winter. About the only days I try to stay off the streets are the days when it is snowing or has just snowed, and they're still cleaning up. Otherwise, I just don't go quite as fast, brake earlier, and take turns with a little easier.

Biggest issue is keeping the bike clean and lubricated properly. You'll want to get the salt and grime off at least once a week. I also run full coverage fenders and larger tires on my winter bike. I'm an advocate as well of just having a second bike for winter/foul weather commuting. On my member page in the slideshow, the orange bike is the one I ride in the winter.

I'm sure you'll have quite a few replies to this one, but likely they'll all tell you that commuting here in the winter isn't nearly as bad as you'd think.
I rode last year even on the coldest days.... My commute is only 3 miles though. The first mile is the hardest but after that you start to warm up. On the coldest days I’d wear a long sleeve shirt and sweat shirt under a windproof shell coat and a scarf… I wore jeans all the time and it worked ok…. I’d put long underwear under it if it was really cold but your legs warm up fairly quickly… My hands and face got the coldest…. I’d wear ski goggles and I’d put the scarf around my face and neck… I wear ski gloves too but even then my hands sometimes got really cold also I wore a winter hat on the coldest days.

I thought cars gave you even more room then in the summer months maybe they feel bad for you but they seem more generous… Riding in the snow can be a lot of fun it’s so quiet… the next day when it turns to ice then you have to be a little more careful.

Get a winter beater if you have a nice bike… my derailleur and most of the drivetrain was shot by the end of winter…I’m hoping that my single speed holds up better this winter.
Here's my kit from last year:

long sleeve base layer (either under armour or wool); just make sure it wicks moisture
wool cycling jersey, sweatshirt, or whatever
outer layer, a shell, etc. if it's really cold, 2 sweatshirts
pair of wicking underwear
long underwear or cycling tights
pair of chrome heavy knickers or pair of military-issue fatigues (aka. BDUs)
pair of smart wool snowboarding socks
pair of double-layer gloves (under layer with fingers, outer are mittens). get these from REI.
Lake cycling boots (damn they're nice)
scarf, cycling cap, beanie, whatever on top. balaclava's are an absolute must.

for the really, really, really cold days, get a pair of ski goggles. seriously, when your tears freeze, it's no fun.

and keep a bag on your back; it's the only time i appreciate my back being warm! :-)

The above kit is only needed at about 25F and below. I don't really ride in ice or snowstorms anymore... I leave that to the other kids.

Just make sure your fingers, ears, and toes are warm and *dry*. Everything else will warm as you ride.
If you're strapped for cash like me I don't think it's necessary to spend a ton of money on winter gear. I guess it's all circumstantial on where you are goin and what you are doing once you get there. Like a couple years ago, i would just wear a parka and something light, like a t-shirt underneath. Of course this wasn't optimal, i sweated like hell. But i just carried another shirt with me. I used (thrifted) wool socks and depending on the pants, long johns.

I can vouch for the gloves inside of mittens deal. Thats the way to go. Even using low quality gloves and mittens, it still worked way better than a pair of expensive snowboarding gloves
Kevin Mulcky said:
If you're strapped for cash like me I don't think it's necessary to spend a ton of money on winter gear. I guess it's all circumstantial on where you are goin and what you are doing once you get there. Like a couple years ago, i would just wear a parka and something light, like a t-shirt underneath. Of course this wasn't optimal, i sweated like hell. But i just carried another shirt with me. I used (thrifted) wool socks and depending on the pants, long johns.

I can vouch for the gloves inside of mittens deal. Thats the way to go. Even using low quality gloves and mittens, it still worked way better than a pair of expensive snowboarding gloves

Yeah, my post was just to give the OP some ideas on what to wear.

I agree: do not spend money until you are absolutely sure that you're interested in winter cycling. And then, start with the most important things to keep warm and work your way inwards.
Thanks for all the excellent advice! I actually snow ski and have heard wearing ski goggles are helpful for winter riding so I will try it out. Additionally (again, since I ski), I have plenty of wicking wear for winter so thankfully I don't have to buy a whole lot of new gear. I do have a 1 year old Raleigh One Way that I use for commuting and would like to keep in good shape and there is the issue of footwear for me. I look forward to facing the poor weather.
Kelly said:
Thanks for all the excellent advice! I actually snow ski and have heard wearing ski goggles are helpful for winter riding so I will try it out. Additionally (again, since I ski), I have plenty of wicking wear for winter so thankfully I don't have to buy a whole lot of new gear. I do have a 1 year old Raleigh One Way that I use for commuting and would like to keep in good shape and there is the issue of footwear for me. I look forward to facing the poor weather.

*mumbling something about looking forward to snowboard season..*
If you're gearing up for the first time on clothes, I'd prioritize good gloves and shoe covers first, maybe balaclava (I only use it for <20 degrees). Dollar for dollar they will provide more comfort, since your core is more easily warmed just by the activity of riding. Then a heavier windproof shell.

I clean my drivetrain more regularly on my commuter in the winter, but aside from that maintenance isn't a huge issue.

Tires/tubes are something to think about. Anyone who has had to change a flat in near zero temps with snow everywhere can tell you it's the low point of winter riding. If you're riding standard 23mm road tires, think about a wear resistant set for winter, maybe even tire liners like Mr. Tuffy.
B said:

I clean my drivetrain more regularly on my commuter in the winter, but aside from that maintenance isn't a huge issue.

This. Also, I'm riding a regular hybrid with brakes, and when it's wet/slushy during the winter, all the road gunk building up on your rims acts like sandpaper on your brake shoes. So I clean the rims after every ride.
What about work clothes? Do you all change/shower at work? I am not sure I can bear lugging extra clothes in addition to a laptop and books.
Regarding keeping your bike in good working order:

I live near Rapid Transit on North Ave, and they have a Winter Bike special that got me through last year. For 100 bucks (single speed) and 150 (gears) they will perform any maintenance from the beginning of winter until april. They will also clean your bike for you whenever you want. All you'll have to pay for (after the initial 100/150) is parts (if necessary) and tips (if you're so inclined). It's something like that, I don't know exactly when it begins, but it must be some time in November.
Clothes:
For most winter weather, I find that I'm fine with a hoodie and a jacket on top and rain pants on bottom. Rain pants are amazing: they're wind proof and they prevent your pants from getting a mess. That way, you don't have to bring extra clothes...you just have to find a place to put the layers once you get inside.

Below 20, I wear thermal tights and something comparable on top...ideally I take them off too once I get indoors.

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