If the amount of time you are spending getting your kids ready to head outside to play is longer than the time you actually play outside… you might be a parent in winter. We have been there, and after winters in several zones of the US with our three boys, we have several snow-tested tips and tricks to cut down on the tears and increase your time actually having outdoor winter fun!

After several frustrating outings a few years ago we realized we needed to switch things up. After a bit of trial and error, and a TON of research, the answer wasn’t actually different activities but rather better gear. As soon as got things right and everyone was toasty warm, the fun followed.

We have mapped out all of our tips and gear recommendations below that we have tweaked and refined over the past few winters with our crew.

child riding scooter in winter
We don’t recommend scooter rides in the snow but sometimes just getting out the door is the goal and naturally, he figured out it was a bad idea on his own after a few near wipeouts.

Getting them out the door

This is often the hardest part. But it gets easier over time and the work you put in when they are little will begin to pay-off as they grow. Our oldest gets himself completely ready and is often a great help for the younger two, this didn’t happen overnight. If you are struggling with a toddler or preschooler, hang in there. It gets better.

children in warm winter gear sledding
They all three will stay out until the street lights come on sledding and rolling around in the snow. Even on days when there isn’t much on the ground.

Gather your gear and dress in stages

Layout everyone’s gear in a contained space (hallway, etc) with different zones and get everyone dressed in stages. This can be modified to meet what works for your family size and needs. At our house, we are usually dressing all three kids and on weekdays, it’s a one-parent show as we alternate work. If we are staying close to home or walking somewhere we have them dress in their base and mid-layers in the living room and then send them for outer layers by the door. This way you don’t have your most cooperative tiny human full bundled and sitting in a pool of sweat while toddlers are being wrangled into fresh diapers. For adventures that require a drive we dress in the base and mid-layers and then pack outer layers, boots, and hats, mittens, etc. in tote bags tossed into the trunk.

Bribery with hot drinks and treats

The promise of a warm thermos of hot cocoa with marshmallows works like magic around here to the little people moving toward the door. I sometimes toss in a sugar cookie as well if I am desperate.

cup of hot cocoa
We drink our weight in hot cocoa in the winter. Its the perfect post-adventure warm-up and a near fail-proof bribery tool.

Unique winter fun for each child

Not everyone has to be doing the same activity to be together. Our oldest loves sledding, the little two love rolling around in the snow. If we announce a sledding trip the middle will fall apart. If we propose a day of “snow adventures” he is all ears. We also ensure we build in success with a bit of pre-planning. On a cold day hike, our little two always have a scavenger hunt list we have hyped up beforehand. We have a whole guide on hiking with toddlers.

child sled riding
Running back up the sledding hill is a lot of work. His wool base layer was working overtime to wick away sweat and keep him from getting wet and cold.

Layering for warmth and climate

Smart layering is the key to keeping tiny bodies warm and dry. Many items are rated for temperature, but humidity and precipitation are far more important. For example, 30 with wet falling snow on a sledding hill in Cleveland, Ohio is going to required very different outer layers than 30, next to zero humidity and glaring sunshine in Boulder, Colorado.

We customize this a bit for each child’s unique needs and the weather of course, but our general guideline is as follows.

Base layer

A fitted non-cotton base layer will hold in body heat and wick away sweat, drying quickly. Merino wool is the best option here, but it’s expensive. If you are looking for all-day adventures or winter camping, this is where you should splurge and invest. Our favorite base layer for the older kids is the REI midweight top and bottom. Our toddler wears the Helly Hansen merino wool baselayer. For a backyard snow-fort building or a short sledding trip, a fitted pajama set will do the trick!

Mid layer

A wool or fleece mid-layer that will provide insulation and trap body heat in the pockets of air between the base layer and the mid-layer. This is the layer to save money! We love Old Navy/ Gap fleece or Patagonia fleece if we can find it on sale or second hand. For younger toddlers and babies, a fleece pajama works great.

Weather-smart outer layer

This is the other area where it pays to splurge a bit. These items have the highest resale value and can also be easiest to snag second-hand. Which outer jackets, snow pants, and snow bibs you need are highly variable based on the climate and winter activities you will be enjoying. We love Patagonia Nano Puff jackets usually worn as their outer layer, but when it’s really cold and definitely back in NYC, they had outer waterproof shells over their coats to keep them dry in the wet snow.

Choosing the best Hats, Mittens, and Boots to keep kids warm in winter

children in warm winter gear building a snow fort
They would have lived in this snow fort if we let them. Waterproof mittens are a must for fort building in the snow.

Mittens vs. Gloves

Mittens will keep small hands much warmer than gloves. And you have ever tried to put gloves on a toddler you already know the frustrating comedy show that is. When the kids are playing in wet snow we slide a fleece liner into their thermal mittens and always have a back-up pair to change out halfway through the day.


A game of preference, choose one that covers the ears and made from synthetic materials or wool. Our oldest loves his acrylic knit hat from his Nana. The middle wears a wool hat I crocheted for him this winter and the littlest is rocking a Patagonia wool hat that was an adult hat that made its way into the dryer and is now toddler-sized. (If you didn’t know… wool cannot be heated in the dryer!– more tips below on making wool last for years.) For especially cold days we include a gaiter of baklava to keep their necks warm.


One pair of thick wool socks is far better for warmth than layering several thin cotton socks that restrict circulation, trap moisture, and actually make their little toes colder throughout the day. We use Real Tree merino blend socks as everyday winter socks since they can go in the dryer. Our first pair lasted two boys over 3 years, which is VERY impressive around here. For longer or colder adventures we slide them into their thicker merino wool blend socks.


This is another one up to personal preference. We have a few brands we love and we look for sales and check all of our second-hand favorite sites (those are outlined below). Our oldest doesn’t like the weight of winter boots so I applied an extra layer of waterproofing spray to his hiking boots and he wears them for most sledding and snow fort building activities. The little guys are wearing Columbia and Sorel boots that are warm and insulating with a sturdy sole and traction for icy trails.

boy dressed in warm layers on winter hike
As a kid I looked like a stuffed sausage heading out to play in the snow, I could hardly move. Quality layers aren’t bulky and keep your kids free to move and explore comfortably.

Final Tips

Keeping wool in great shape

We use Woolite to wash our wool layers every 10-15 wears. Hats and gloves only needwashed 1-2 times each winter. Because wool is naturally anti-bacterial you don’t need to and shouldn’t wash after each wear. Line drying is a must.

Where to find second hand gear

Finding great second-hand children’s gear is a bit of extra work and effort, but we have scored great deals and stocked up on quality gear for a fraction of the price.

Facebook Marketplace
Outdoor Gear Exchange
REI Used
Worn-Wear from Patagonia

Enjoy your winter adventures with the kids and do tag us on social media @fivepax or drop us an email at [email protected] Stay safe and warm!

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