Hiking a fourteener in winter is nothing like hiking one in summer. You can’t stuff a pack with snacks, a couple of water bottles and some extra clothes and then head out expecting success. The risk and difficulty increase significantly.
Most of Colorado’s fourteeners are considered a mountaineer’s kindergarten playground during summer. Trying one during winter is a good first step into the world of real mountaineering.
I have successfully summited fourteeners 20 times in winter, have had eight failed winter attempts, been part of a number of winter alpine rescue missions and participated in several winter overnight training sessions in temperatures as low as minus 30. While this doesn’t come close to making me the most experienced person in the Rockies, I have learned a few helpful tips along the way.

LEARN TO LAYER

Use clothing layers well and invest in a shell of clothing that is waterproof and breathable. If you have a solid shell, then your layers don’t need to be anything fancy, as long as you avoid cotton. Don’t forget layers for your head, face, neck, feet and hands.
Be proactive in adjusting your layers. When you stop to take a rest, put on additional layers before you feel cold enough to need them. Pause before you reach a ridge or a saddle and zip up your shell layers. Winter winds blow harder and will steal your body heat if you don’t seal them out.

PROTECT YOUR WATER

Just because it’s cold doesn’t mean your body’s need for water decreases. You will be working hard to climb the mountain. But carrying enough water does you no good if you can’t drink it.
In winter, I give up on my hydration packs. Tube insulators, blowing out the tube between uses and putting the pack inside my jacket have all failed me. I stick with large-mouth water bottles, keeping one in an insulated pouch that is easily accessible. It’s best to store it upside down as any ice that forms will be at the bottom of the bottle. I keep additional bottles in my pack, wrapped up in my emergency gear and extra clothing.

PLAN FOR SNOW

Bring footwear traction appropriate for your terrain whether it’s crampons, snow/ice traction devices or just a pair of boots with good lugs.
Bring snowshoes (or skis) for deep snow. I don’t like snowshoes; they are awkward and tiring. However, I hate post-holing — when you step on the snow and your foot punches through. Then, as your next step is about to get you out of that hole, that foot punches through. This leaves a trail of holes that look like fence post holes.

CARRY AN ICE AXE

You can find trails that don’t go into terrain where you’d need one, but getting off route in winter is common and an ice axe can save you in a bad situation. The basic use of an ice axe is to help you stop in an uncontrolled slide. There is little time to respond, so make sure you’ve learned to use it properly.
Know how to navigate your route without any clues besides the topography. Snow can obscure a trail and even your own tracks might be swept away behind you in seconds.
Most importantly, be prepared for avalanches. Take an avalanche-awareness class (at least) and make sure you - and everyone in your group - have the proper equipment and know how to use it. At a minimum, this includes an avalanche beacon, probe and metal shovel. Don’t skimp on this equipment.

TAKE A HEADLAMP AND EXTRA BATTERIES

The math is pretty simple. Hikes take longer in winter, and daylight lasts as much as 6 1/2 hours less. Put those together and you’ll likely be hiking in the dark.

BE PREPARED TO SUCCEED

Plan ahead. Know how close to the trailhead you’ll be able to drive. Pay attention to the snowfall that occurs in the weeks preceding the hike. Try to pack as light as you can without leaving anything behind you’ll need. Get in shape and lose weight if you’re carrying extra pounds.

BE PREPARED TO FAIL

I don’t advocate giving up when things get hard. Mountaineering involves persevering through a lot of difficulty, but at some point continuing to push on risks too much.
Also be prepared for when things go wrong. Make sure you have the gear needed to spend an unplanned night out.
Taking on such a challenge is to experience the real Colorado, rugged and untracked wilderness. You might even experience a modern-day rarity — solitude. The price of admission to the fourteeners in winter is high, but the splendor is all the more rewarding.