Paul Terefenko of NOW Magazine has some pretty good winter cycling tips but I feel I can provide better suggestions in places (having taught CAN-BIKE and ridden in many winters).
Just ditch style in the winter. That Pashley doesn’t deserve to get eaten by salt, covered in grime and penetrated by water for four months. Instead, find a beater.
Get a bike with as few gears as possible. Frames don't rust quite as easily as NOW suggests, just shake or wipe it off frequently. The real issue is rusting of gears, brakes, and cables.
Choose a more upright bike that allows you a better field of vision.
Something with wider knobby tires works.
There is almost no advantage to knobby tires on Toronto streets. When the roads are icy knobs don't help you, and when it's snowy you almost want a bike with thin tires that can cut through the packed snow.
There are studded tires out there, if you’re convinced you need them, but again, Toronto roads are pretty well cleared most of the time, and you’ll just be buzzing along most of the time.
Studded tires would be quite nice on ice, particularly on side roads, but you can get by without them.
Gears are nice, but can freeze. Make sure to lube brakes, gear cables and your chain. A lot.
Use lots of lube (and by lube we mean bike chain specific lube). Heavier oil is better in winter since it doesn't wash off as easily, but it will attract a lot of dirt and grit.
The fewer the gears the better. You will better off with a well-built three speed internal gear hub, a fixed gear, or a coaster brake (where you pedal backwards to stop). These all have fewer issues with cables freezing up.
An ideal winter set-up would be a fixed gear bike with disk brakes, which would give you the least chances of brakes failure. But this may also be overkill or hard to find if you're looking for a used bike.
Ice and Salt
Freezing is also made a whole lot worse if your beater is going indoors between rides. Any ice buildup melts and then refreezes when you go back outside. Keep it outside – that’s why you’ve got a beater.
Probably a good idea to keep the beater outside unless you can clean off the snow before bringing it into a warm space. The big issue is the water mixing with salt as the bike warms up which increases the rusting.
Riding with care
Starting slowly is key. When your body isn’t warmed up the frigid temps are taking a toll on your joints. Warm them up just like you would a cold car engine – i.e.: don’t floor it.
Most likely you'll be starting having just left indoors so this isn't usually a concern.
Once you’re moving keep yourself in a straight line, especially over ice and snow. Also avoid the front brake over slippery roads. Using it increases the chance of the front wheel sliding out.
Always, always use both brakes! The key is not to use the front brake too much. Terefenko's advice is poor: only using your rear brake increases your chances of the rear wheel sliding out and takes you longer to stop. Just use both brakes, applying slowly, and push your weight backwards on the bike to help prevent yourself from pitching over.
It’s a good rule-of-thumb to avoid streetcar tracks at any time of the year, but wet, slippery rails are so much worse in the winter. The same applies to metal bridges, plates and even painted lines.
Terefenko fails to explain how to cross streetcar tracks. Slow down and cross the tracks at close to 90 degrees as is possible. If you are riding alongside them, slow down, shoulder check to make sure the way is clear, turn away from them a bit, and then cross them more sharply. No braking or leaning during the turn.
Most of the time, you won’t even encounter crazy conditions – just former crazy conditions in the form of encroaching snowbanks that push you closer to traffic. The city’s supposed to be on top of this, but that statement applies to lots of reality defying issues.
The city is slow in plowing the bike lanes, but it's starting to happen as I've seen on College St and elsewhere. Last year was the first year that the city plowed the Martin Goodman trail. It's a much less stressful alternative to the streets!
You need to be careful to not ever make quick turns, no leaning into turns, and no quick stops or starts. On ice or streetcar tracks keep
Like any active sport, layering is key. You’re going to heat up in the core, and conditions can change, so base layer, mid and shell, is the standard. The shell should be waterproof, and again – style will suffer, unless you’re still into that mid-90s urban explorer dad look.
Don't worry about layering unless your commute is long. Most people who go less than 40 minutes can just wear a regular winter jacket, sweater and t-shirt. You don't need a waterproof jacket if it's cold since nothing is melting.
Footwear has to be waterproof. I found some winter hikers for $70 last year, and they’re amazing. They also negate the need for those cycling dog booties.
Just use regular warm winter boots. I use either hiking shoes or Blundstones with heavy socks. Both are somewhat waterproof, but again, no need for waterproof unless things are melting.
Pants are another story. Jeans don’t really work – but you can usually swing it with a good pair of thermals underneath. For those not-so-cold moments, you can try windproof underwear. They counter the crucial groin chill.
I wear jeans with long johns. They work just fine for me. If it gets colder you can pull on rain pants. Perhaps you have less natural padding and will need more.
As for your hands and head, they’re at the top of the list. Your hands are fixed in place, so you can’t just heat them up as your ride. Ski gloves (not mitts) do the job. The head is tougher.
Always choose mitts over gloves. They just keep your fingers warmer. I put a thin wool glove underneath thick mitts.
Balaclavas are great, but you can get by with a good thin toque under your helmet. It sure beats squeezing into a hood, which flies off, impairs vision and tends to channel air into your jacket. Some people do the ski goggles, too.
A thin toque under the helmet works well, or even a shower cap over the helmet to keep the wind out. Ear muffs help a lot. I've got facial hair so I don't worry about the lower half of my face.
Like Terefenko suggests, put your bike on the bus bike rack when it gets too cold or you're too tired. On the worst days just leave your bike at home. After a day or two things will usually clear up and you'll be happily biking again.
Happy winter cycling!