Hiking With A Toddler: Gearing Up for Winter

Part three of the Hiking With A Toddler series: Gearing Up for Winter • twokidsintow.com

It’s slow this year, but it’s happening: the temperatures are steadily dropping and the forecast is littered with promises of snow here in Colorado. Although this isn’t my first winter with kids, this is the first winter I am planning on continuing our regular outdoor excursions instead of hiding inside for months on end. With the proper precautions and necessary compromises along the way, my hope is to embrace the change in seasons and continue hiking and exploring the outdoors through the colder months of the year.

For the past few weeks, I’ve taken notes from my favorite blogs on how to dress to stay warm and comfortable outside in the fall and winter months. Some of these articles deal specifically with dressing young children, while others are written more generally. With a few special considerations for babies and toddlers, recommendations for dressing appropriately for winter activities are largely the same for adults and children.

Appropriate winter dress is achieved in three layers:

  • Base layer, worn next to the skin to wick away sweat and keep the body dry
  • Insulating mid-layer, worn over the base layer to keep the body warm
  • Weather-proof outer layer, worn over everything else to protect the body from the elements

Merino wool or poly-blends are the best choices for base layers, as they wick away sweat and breathe well. Avoid cotton and cotton blends if you can, as wet cotton will leave you damp and cold.

For your mid-layer, fleece is great to add warmth without the additional bulk. A fleece jacket with fleece leggings worn over your base layer will keep you warm when it’s especially cold outside.

To protect yourself from the elements and keep everything dry, wear a waterproof and wind-proof shell over your mid- and base layers. Rain or wind jackets paired with rain pants will keep out the moisture and protect you from the wind.

I have been slowly working on building up Luke’s winter stash and I’m starting to feel pretty good about moving into the colder months. There are a few things I will be able to reuse this year, but after the massive amount of growing my son has done over the last few months, I’ve had to shop for most of this year’s gear. I’m fairly confident that I’ll get at least two years out of most of what I’ve bought in the last few weeks, due to the sizing and the quality, and even longer when you factor in that all of this stuff will be saved for little brother.
Part three of the Hiking With A Toddler series: Gearing Up for Winter • twokidsintow.com

This post contains affiliate links. For more information about how affiliate links are used on this blog, please read my disclaimer.

So far, I’ve done most of my shopping at REI, REI Outlet, and Amazon.

After reading through many different reviews, I bought REI– and Helly Hansen-brand base layers for Luke. Although we aren’t very far into the season yet, I have been incredibly happy with the quality of these base layers so far. I also bought a number of pairs of REI merino wool hiking socks that I’m certain will last for quite some time.

I bought REI heavyweight long underwear top and bottom for Luke to wear as a warm, fleece mid-layer when the temperature really drops. At the moment, I typically pair a fleece jacket from Costco with a pair of base layers for our hikes and that combination keeps him plenty warm and comfy. (Confession: I have yet to find some good pants for Luke, so unless it’s really wet and he wants to splash in some big puddles, I throw on a pair of jean overalls over his base layers. Do you have any suggestions for sturdy, warm pants?)

When it’s a little wet or windy, I break out the REI rain jacket to wear over his fleece layer. Miraculously, this will be the third year we’ve used this jacket and it is still in excellent shape. I have an older pair of REI rain pants that I pair with the jacket and sturdy rain boots for some serious puddle stomping. (These pants are also going on three seasons old and a bit too short for my tall boy, so I’m eyeing a pair of Oakiwear rain pants to replace them this year.) For very cold snow days, I have Luke wear a two-piece snowsuit, bought this year at Costco, over his fleece layer.

I have a new pair of Sorel snow boots waiting for our first heavy snow, an old pair of well-loved Hatley Kids rain boots for super wet days, and a trusty pair of waterproof Keen hiking boots for just about every other outdoor adventure.

I have a pair of waterproof REI mittens from last year that will continue on through this season and possibly the next. If I’m carrying Luke for the entirety of our hike and it’s cold but not too windy, I’ll put a cheap pair of gloves on him so he has something over his hands. I’d like to upgrade these at some point, but I have yet to find something I like that is lighter than the big waterproof ones but warm enough on their own.

And last but not least, I have a favorite favorite favorite fleece-lined, wool hat from Germany that will be big enough for its third season of use before it makes it way into our little brother box. I’d like to try a balaclava this year, but I’m not sure if Luke will dig it or not.

Take a look at the following articles from my favorite blogs for more in-depth tips on how to layer for outdoor winter fun, as well as some specific gear recommendations:

Washington Trails Association: Keep Kids Warm and Happy on Trail this Fall

Hike It Baby: Winter Hiking With Babies, More on Winter Hiking With Infants, Toddlers, and Children, and Winter Gear – How to Layer

Moms Who Hike: How to Dress a Kid in Layers, How To Keep Little Feet Warm, and How To Keep Kids Hands Warm

The Outbound: 7 Surefire Ways To Stay Warm On The Trail

We are at the very beginning of the cold weather season and will obviously need to adapt as the temperature continues to drop and the snow begins to fly. I plan to add the lessons I learn throughout the winter to my Hiking With A Toddler series, so stay tuned for updates as time goes on!

More from the Hiking With A Toddler Series:

Hiking With A Toddler: What To Bring

You've done your research and chosen the perfect hike. Now that the 'where' is taken care of, what do you need to bring with you? This post contains affiliate links. For more information about how affiliate links are used on this blog, please read my disclaimer. ON...

read more

Hiking With A Toddler: Choose Your Hike

It's the first week of summer! The weather is nice and the trails are beckoning. Over the next few weeks, I will be sharing some basic tips, tricks, and tutorials to help you get out and hike with your toddler. This morning, I will walk you through how I find and...

read more

About The Author

Jessie Emslie

Jessie Emslie writes from her home at the foot of Pikes Peak in Colorado Springs, Colorado, where she lives with her husband, her two boys, and her dog and cat. She is happiest exploring the outdoors with her baby on her chest, her husband and her toddler by her side, and her camera in hand. Jessie documents her everyday adventures on Instagram and her blog, Two Kids in Tow, where she shares stories, tips, and guides to inspire other young families to go outside and explore the world together.


  1. Rebecca

    Great blog post! My kid wears Costco fleece jacket too…and I love it when I can find something affordable that works 🙂

    • Jessie Emslie

      Thanks, Rebecca! I’ve been stalking the aisles in hopes of finding one my size. Such a great little jacket!



  1. Looking Ahead: Preparing for Cold-Weather Adventures - Two Kids in Tow - […] outer layers for baby brother (you can read more about this layering system in my original Gearing Up for…
  2. 4 Tips for Outfitting An Active Winter Pregnancy - Two Kids in Tow - […] is here and it’s here to stay! You’ve done your research and now your toddler is geared up and…
  3. 5 Ways to Make Winter Adventures More Enjoyable - Two Kids in Tow - […] Kenosha Pass Camping Trip My 52 Hike Challenge: Conclusion Hiking With A Toddler: Gearing Up…

Leave a reply

Your email address will not be published. Required fields are marked *

Hello, I’m Jessie

I write from my home at the foot of Pikes Peak in Colorado Springs, Colorado, where I live with my husband, my two boys, and my dog and cat. I am happiest exploring the outdoors with my baby on my chest, my husband and my toddler by my side, and my camera in hand. Read more...

November 2015
« Oct   Dec »