Preparing for Winter Hiking: What to Wear, How to Layer & What to Bring

We are in the heart of winter hiking season – the most wonderful time of the year! ❄️

With our next hike up Mt. Tecumseh on 2/7, followed by Mt. Willard on 2/21, and our final winter hike of the season on Cannon Mountain on 3/14, I wanted to share some practical guidance to help you feel confident, comfortable, and prepared for your next cold-weather adventure.

Winter hiking is peaceful, quiet, and more gentle on the joints, but it does require preparation. This is not a “less is more” situation. In winter, it’s always better to be prepared, not sorry.

Below is exactly what I wear and recommend, from layering properly to the essential gear you should always carry.

HOW TO LAYER: What to Wear From the Inside Out

Layering properly is the single most important part of winter hiking. The goal is to stay warm without overheating, and to manage moisture as your body temperature changes.

1. Base Layers (Top & Bottom)

Light- to midweight non-cotton, synthetic or wool materials

Cotton traps moisture. Avoid it at all costs!

2. Socks

Smartwool mid-length socks

Always pack two pairs in case one gets wet

3. Pants

Winter hiking pants (I love the EMS Ascent Series)

Look for breathable fabric and zippered vents

4. Insulation Layer

Patagonia Women’s Nano Puff Jacket (my go-to)

Lightweight

Packable

Weather-resistant

Works solo or under a shell

Perfect for all four seasons

5. Outer Shell

Lightweight, breathable, waterproof shell

I wear The North Face Freedom or Summit Series, depending on conditions

6. Accessories

Insulated neck warmer

Warm winter hat

Waterproof gloves (I swear by HESTRA Gore-Tex gloves)

💡 As you hike and warm up, you may remove layers – often the puff or shell. Always carry an extra fleece  or flannel in your pack just in case.

WINTER HIKING GEAR: What to Have With You

Here’s what I recommend carrying for a safe and enjoyable winter hike:

A 20L backpack with hip and shoulder support

Waterproof winter hiking boots with ankle support.  highly recommend SCARPA (this is what I wear)

Hydration:

1. 1L insulated thermos (hot water or tea)
2. 1L cold water
3. I use Stanley and YETI brands

Snacks you can eat while walking:

1. Protein bars, trail mix, apples
2. Include both salt and sugar in your pack

Electrolytes: I use LMNT and wouldn’t use anything else:)

First aid kit + emergency blanket (if you hike with us, your guide will have this so you do not need to carry it also)

Traction:

1. Snowshoes if packing trail
2. Microspikes always – even if you don’t expect to use them

Trekking poles

Hand warmers

Cell phone or SOS device (SPOT or similar)

Why You Should Hike With a Group in Winter

Winter hiking is incredibly rewarding… quiet trails, crisp air, and stunning views – but it can also be unpredictable and dangerous, especially if you’re alone.

I strongly recommend hiking with a group or a guide, especially in winter. Conditions change quickly, and having experienced leadership and community makes all the difference.

Our guides are all WFA certified and we are under permit with the White Mountain National Forest. This means you are in good hands and our guides are well trained.  Being under permit with the WMNF also means that they know we are out there, they have our schedule and know what trails we are taking, and this helps to track us in case of an emergency.

Final Thoughts

I hope this guide helps you feel more confident preparing for your next winter hike. If you have questions or want help dialing in your gear, feel free to reach out to us at supyoboston@gmail.com.

👉 You can also use this coupon to order my favorite Patagonia Women’s Nano Puff Jacket:
Patagonia Coupon Link

Plan. Prepare. And have fun!

If you felt this was helpful but would like to watch a more extended video version of prepping for your next outdoor adventure, we do have a great video here. Feel free to download and watch at your leisure:

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We look forward to meeting you outside!