8 Steps to Enjoying Cold Weather Running

Dressing properly for cold weather is the key to running comfortably throughout the winter. You should dress in thin layers made of synthetic materials that wick away sweat and dry quickly. By wearing layers, you can regulate your body temperature by adding or removing layers as you warm up or the weather conditions change. Stick to technical running clothes and avoid cotton, like sweatshirts and sweatpants, since they'll absorb and retain water.

Also see:
How to Dress for Cold Weather Running
Men's Cold Weather Running Clothes
Women's Cold Weather Running Clothes

This is along the same lines as step #1. It's important that you're dressed warm enough to prevent serious conditions such as hypothermia and frostbite. Another danger of winter running is limited daylight, so you need to make sure you're wearing reflective gear and can be seen when running in the dark or low-light conditions.
Also see:
Cold Weather Running Safety Tips
Reflective Gear for Running at Night

Generally, heat loss from just your head is about 50% when the temperature is at the freezing mark. Wearing a winter hat made of a warm fabric like wool or fleece can help you stay warmer and comfortable for longer periods of time.
Also see:
Men's Winter Running Hats
Women's Winter Running Hats

As long as I'm dressed appropriately for cold weather running, it's that first mile that is really the toughest. Once I make it through that, I'm warmed-up and feel comfortable for the rest of my run. To make that first mile a little more bearable, I'll sometimes warm up inside with some jumping jacks or jogging in place. Here are some other ideas for getting through that first cold mile.

You can lose as much as 30% of your body heat through your extremities. And lower temperatures cause blood to be shunted away from your hands and feet to keep your internal organs warm and protected, so it's important to keep your hands and feet protected and warm.
Also see:
Top Running Gloves
Winter Running Socks
How to Keep Your Feet Warm During Cold Runs

Worried about slipping or sliding on the snow and ice? If you take the right precautions, you can still run outside and be safe. For example, some runners wear Yaktrax Ice Grippers or ice traction cleats on their running shoes to improve their traction on the snow and ice.
Also see:
Tips for Running on Snow and Ice

Make your chilly runs a social event and you'll find yourself actually looking forward to them. Find a local running group or recruit a friend to run outdoors with you. Knowing that someone is waiting for you will help motivate you to do those cold weather runs. Then, once you're done, you can grab a coffee or hot chocolate together.
Also see:
How to Find a Running Group
How to Find Running Partners

Signing up for winter races is also a great way to stay motivated and to guarantee that you won't run alone. Yes, you need to plan your race outfit a bit more carefully than you do for warmer weather races, but you'll find that cold weather races are less crowded and you'll get more bragging rights for having finished a race in freezing weather.
Also see:
Tips for Racing in Cold Weather