Let's start with basic, relatively inexpensive personal gear. Every hiker, runner, or cyclist either needs or wants another hat, t-shirt, socks or gloves. Moisture wicking t-shirts can be a life-saver in any season by pulling body temperature reducing water away from the body. And gloves with conductive finger tips that allow the use of cell phones with out exposing fingers to the cold are very useful during the winter months.
Staying with personal gear, but moving up the cost ladder a little bit, consider hiking boots. Keeping with the cold weather theme, look for insulated hikers. Different than big, clunky "snow boots," insulated hikers flex, fit and feel like regular hiking boots. The difference is they usually have Thinsulate to keep the feet warm, a sole compound that is a little sticky to help when on ice, and are waterproof. I have a pair made by Salomon that I've been wearing for a few years.
Along with boots, consider some traction aids such as YakTrax or Kahtoola for icy conditions. If you want to step it up a bit more, so to speak, look into a pair of snowshoes. Hiking poles are also good year round, especially for the backpacker on your list, since they make hiking with heavy loads a bit easier. You can't go wrong there.
As far as technology goes, a handheld GPS will help keep the person on your list safe, can track their hikes, or plan a route. Also, a Personal Locator Beacon or an avalanche beacon for those you-hope-they-never-happen emergency situations. Bluetooth ear warmers will let the person on your list listen to their favorite music or podcast with warm ears while on the trail.
Then there's the always tried-and-true gifts for outdoor lovers. Pocket hand warmers, guidebooks, state and federal park passes, and especially gift cards are great for the hard-to-buy-for adventurer, and maps make great stocking stuffers, too. Locally produced Pocket Pals Trail Maps recently announced some new maps and updates to existing maps, and are on sale right now.
Bob Falcone is a retired firefighter, photographer, hiker, business owner and author of Hiking Bob's Tips, Tricks and Trails, available via his website. He has lived in Colorado Springs for more than 26 years. Follow him on Twitter (@hikingbob), Facebook (Hiking Bob), Instagram (@HikingBob_CO) or visit his website (Hikingbob.com). E-mail questions, comments, suggestions, etc to Bob: email@example.com.