Your Guide To A Winter Hiking Date   

Your Guide To A Winter Hiking Date   

There are many ways to spend a cute and cozy time together in the winter months. But when you’ve been ice skating, you’ve visited the markets and you’ve given up trying to build a gingerbread house that doesn’t look like it’s been hit by a natural disaster, what else is there?

Once sledding and snowmen have lost their charm, it’s time to take things up to the next level with a winter hiking date. Imagine just the two of you, out in the wilderness, tackling a physical challenge together, breathing in the fresh air and looking at the stunning views, gloved hand-in-gloved hand.

But winter hiking isn’t something you can just decide to do on the spur of the moment. Of course, you need to plan for it, so we’ve created this guide, covering hiking outfits, whether you should hike on a first date and much more.

What to wear on a Winter hiking date

Let’s get to the most important issue first. What to wear when hiking in the winter. Because this is a date, right? So you need to look good. But it’s hiking. In the winter. So you need to be warm. And being warm and looking good at the same time aren’t always compatible, especially if you’re up in the hills or mountains where it’s even colder.

So here’s our guide:


There’s nothing that can be done here beyond just getting the right footwear. It might be big and clunky-looking and the word ‘cute’ has never been used about walking boots, but it’s even more essential in the winter that you’ve got footwear that will keep you safe and dry. Because there’s nothing cute about trench foot or falling on your butt every five minutes.


Again, there’s not much that can be done here. Hiking in the summer means you can show off your legs in cool shorts, but in the wintertime, you need to bury those pins underneath layers of thermal leggings, thick joggers or insulated pants. They might not flatter you, but they will stop the wind chill from biting.


No strappy tops or funky t-shirts here, you need a thick woolen turtleneck or fleece sweater and a warm and waterproof jacket to wear over the top. Of course, wooly sweaters can definitely look cute, but functionality is what will matter when you’re standing on a snowy peak gazing out at the beauty and remembering how long it will be before you’re back somewhere with a fireplace and hot cocoa.


So far so dull, right? Winter hiking date outfits aren’t known for their variety or attractiveness but with the right accessories, you can still make sure your date is impressed. Hats, scarves and gloves are all essentials for a winter hike outfit but at least you can find the right ones to match your look and command some attention.

First date hiking considerations

So, we’ve covered cute hiking outfits (at least as much as we can in the winter weather) but what else do you need to consider for a hiking date? Here are some ideas and tips to make sure your date goes smoothly and creates memories for a lifetime:

First date hiking

Is a hike for a first date a good idea? Well, that depends on the two of you. If you’ve come together over a shared love of hiking, then maybe it is, as it takes away some of the pressure and awkwardness of a traditional first date.

Of course, you need to consider personal safety when going into the wilderness alone with someone the first time you’ve met them. Perhaps you should meet up for a chat somewhere first so you can get to know each IRL before undertaking this date? Certainly, you need to tell a friend where you’re going and when you expect to be back.

When on the date itself, you need to make sure that you’re being considerate of each other’s levels of physical fitness. There’s nothing sexy or romantic about exhausting your date by dragging them up a mountain at high speed.

Where to go?

Planning where you go on your hike is an important stage in winter hiking dates. You need to make sure the route is safe (especially paying attention to current weather conditions) and suits the hiking experience you each have. Getting this wrong could end in disappointment, embarrassment or even much worse.

A winter hiking date can also be a key part of a weekend away in a beautiful log cabin, where you can get cozy once you’ve gotten back after the hike and stripped off all those layers of thermals. Blankets, hot chocolates, good books and even better company are all well-earned after a long hard hike on a winter’s day.

Don’t forget the essentials - 

Going winter hiking on a date means needing to remember lots of essentials. You’ll certainly need a flask of something warm for when you have a break and some snacks that will help to replenish your energy, like nuts, chocolates, fruit, etc.

Also, when choosing your cute hiking outfits for the winter, remember that you may need to pee at some point, so making this as quick and easy as possible both for the sake of dignity and staying warm is definitely essential. Well, as much dignity as you can manage in the circumstances. If you’re on a first date… good luck!

Things to avoid  

Finally, there’s what not to do. Definitely don’t try and calm your nerves beforehand with a drink. You may be on a date, but this is a date with snow, ice, loose rocks and dangerous heights, so you need to be focused and sober. Also, alcohol can give you a headache and make you dehydrated. Save it for the celebration when you’ve made it to the end.

Most of all, avoid risks. If you have any red flags about your date or the weather or your health, take them seriously and ask for a raincheck. Have a backup plan in mind and if you end up not hiking, no-one will end up too disappointed.