Winter brings magical snow-packed adventures, crisp mountain air, and glittering ice—but it also brings the challenge of staying warm and dry outdoors. Proper preparation is all you need to stay comfortable and avoid the chilling cold, whether sledding on Mt. Hood, taking a frosty hike along the border of Idaho in Hells Canyon, or hitting the slopes at Timberline Lodge.  

Families and adventurers alike can learn tips that highlight how to stay dry and warm in any winter outdoor activity. Everyone can stay comfortable while enjoying the season, from toddlers to grandparents.

Layering for Total Warmth

Layering is the golden rule to staying warm in most winter climates. The first layer should be a moisture-wicking top made of wool or some type of synthetic material that pulls sweat away from your skin. You may think cotton will work fine, but it traps moisture, which will only amplify the cold.

The next layer should insulate you and trap heat, so wear fleece jackets or puffer coats. The last layer should be an outer shell that offers wind and water resistance. Make sure every layer fits snugly without restricting movement so you can stay warm skiing, snowshoeing, or on a winter boat tour.

Tips for Dry Feet and Hands

Nothing ruins a winter adventure faster than frozen toes or soggy gloves. Choose insulated boots that are ready for any weather, from rain to sleet to snow. Keep your feet warm and dry, even during all that sledding, by wearing wool socks, not cotton. Wool repels water, while cotton socks will just soak it all up.  

Invest in waterproof gloves or mittens for your hands. Mittens keep kids’ hands warmer since their fingers tend to stay close together, creating more heat. Bring a dry spare pair to quickly save the day if gloves or mittens get wet.

Head-to-Toe Protection for Everyone

A good hat that keeps heat from escaping is extra helpful for staying warm. Insulate your head any way you can; look for wind-resistant beanies or headbands that fit comfortably under snowboarding helmets. Scarves, neck gaiters, or balaclavas can also shield your neck and face from cold mountain breezes.

Little ones especially need extra attention to keep their ears and heads warm. Look for hats with built-in ear flaps—perfect for adorable family photos at Bend’s WinterFest.

Prepare for Unpredictable Weather

Weather in the Pacific Northwest changes quickly. Check the forecast before heading out, and avoid going if you predict dangerous conditions. No matter what, always pack for the unexpected. Toss an extra sweater, gloves, and snacks into your pack; you’ll thank yourself if conditions change. 

Waterproof bags and an emergency kit are lifesavers for camping in snowy areas, fishing in icy spots, or other long excursions—not to mention it’s essential for keeping up with Oregon’s unpredictable mix of rain, frost, and snow.

Closing Thoughts

The chill and cold of winter don’t have to stop you from experiencing outdoor adventures. With some practical planning and smart choices—such as waterproof boots, layered clothing, and an emergency stash of gloves—the whole family can learn how to stay dry and warm in any winter outdoor activity. Staying warm and dry is easier than you might imagine. 

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