The Hiking Date: How To Plan The Perfect Date And Avoid Potential Pitfalls

You and your partner both love to be outside and enjoy all that nature has to offer, but how do you plan that perfect unforgettable hiking date?


To plan the perfect hiking date, you should make sure you make a plan, bring enough food and drink, and choose a trail that’s appropriate for all skills levels. Before your hike, make sure you watch the weather, dress for an active day, and eat a good breakfast.

Whether you’re planning your first date with someone new or taking your long term partner on a new kind of adventure, the hiking date is sure to be a date that neither of you will ever forget. While there are several ways to make your hiking date perfect, there are several pitfalls that you should watch out for. Read on to discover how to plan the most amazing hiking date, what to bring, and how to choose the perfect trail.

By the way, as an Amazon Associate, I earn when buying qualified products through links on my site.

8 Ways To Make a Hiking Date Amazing

Now that you’ve decided to take your date for a hike, it’s time to discover the best ways to make this date one that neither of you will ever forget!

Make A Plan

This tip may be obvious, but making a plan to go on a hike is a great place to start with planning your adventure. While there is a time and a place to go on the spontaneous hike, you’ll want to spend some time planning a hike on a new trail (or with a new person). You’ll want to know how long the hike is, what the trail is like, and what the scenery will be so that you can plan the perfect date.

It’s not a bad idea to hike the trail beforehand to get a better idea of what the trail is like.

One important benefit of having a plan is that you can tell someone where you’re going, and so can your date! This brings much more safety and accountability to the date.

Start With Breakfast (Or End With It)

A nice morning hike and some breakfast, sounds great, doesn’t it? If you’re planning a morning hike, you generally have three options as to when you eat breakfast:

  1. Before
  2. During
  3. After.

This seems redundant, but there’s plenty of planning that goes into each option.

If you’re eating before you hike, you won’t want to eat a huge breakfast, otherwise you’ll feel sluggish on the trail. Instead, start your day with a granola bar or some other good source of protein and grab your favorite morning beverage for the road. Or, you could bring your granola bars with you and eat them as you hike.

If you’re hiking before breakfast, you could plan to stop at a restaurant after you get off the trail. This way, you’ll have some yummy food to look forward to! However, make sure you pack a small snack to hold you over, you don’t want to be too hungry on the trail.

Pack A Picnic Lunch And Snacks

What’s more classic than a hike and picnic lunch? Hiking mid-morning or mid-afternoon is a great time to hike because it’s not too hot and not too cold. Plus, you can pack a fabulous lunch and some extra snacks. Here are some options for the perfect picnic lunch:

  • Sandwiches (bought from a store or made at home)
  • Cheese and crackers
  • Summer sausage or beef jerky
  • Nuts and fruit
  • Chips or pretzels
  • Hummus (goes great with veggies or crackers)
  • Veggies (carrots, celery, tomatoes, etc.)
  • Dessert (cookies or candy are always good options!)

These hiking snack ideas are just the beginning. To see dozens of ideas with pictures, check out our mega list of hiking snack ideas for every situation (and diet).

Any time you’re hiking, camping, or going for a walk outside, you need to Leave No Trace. This means that what you bring out on your hike, you always take it back out with you. By cleaning up our trash, we respect the environment and keep our trails clean.

Besides the draw that food has because it’s… you know… food. A picnic is a great way to make the date memorable–and gives you a chance to talk and enjoy each other’s company.


Water is one of the most important things you should bring on your hike. If you’re dehydrated, you might get a headache, feel tired, and have that horrible feeling of sandpaper in your mouth. All these can be avoided by bringing a water bottle or two. You should always bring water, but there are some other ways to keep yourself hydrated.

Some other drinks you can bring to make your hike more exciting may be:

  • Sports drinks like Gatorade or Powerade
  • Coffee
  • Hot chocolate
  • Apple cider
  • Sparkling water

Hike At Sunrise Or Sunset

The golden hour is prime time to go on a hike, so plan your hike for sunrise or sunset. Trust me, getting up early to hike to the top of a trail and watch the sunrise is worth it. But if mornings aren’t your style, then grab some flashlights or headlamps and head out for a sunset hike and some stargazing.

Take Pictures

A picture is worth a thousand words. Whether you want to post on social media or need a picture to show off your new date, pictures are always worth it. You don’t even need a fancy camera, just grab your phone and take a selfie!

Be careful of sharing pictures of each other on a first (or even second) date–some dates may consider that awkward. But if your relationship goes somewhere, you’ll be glad to have the pictures!

Choose The A Hike For All Skill Levels

For most hiking dates, you’ll want to choose a trail that is rated as moderate or easy. If you and your partner are more seasoned hikers, you can discuss whether you want to choose a trail that’s more difficult.

This is not the time to show off how adventurous you are. As tempting as it may be to bring a date to a technical climb or downhill, it’s extremely likely that the experience will not be the same for your date as it is for you (if they are not accustomed to hiking or scrambling, especially).

Hiking Date Ninja Tip: Choose a Wide Trail, If You Can

While not every location has this option, choosing a wider trail has multiple benefits. Not only is a wider trail likely to be an easier one, but you’ll have the chance to walk side-by-side and have those meaningful conversations. If you hike on a narrow trail, it may be more difficult to hear what your date is saying, and you may end up walking in silence, yelling, or repeating yourself.

A nice wide trail that can fit two people walking side by side

I’ve spent countless hours hiking in single-file over the years and I can tell you, that you can’t hear someone very well speaking in front of you if they are just talking in a conversational tone.

Of course, hiking a wider trail is not absolutely necessary for planning the perfect hiking date. You can always hike in single file and talk when you take a break to catch your breath or reach your destination, or if you don’t mind talking loudly.

Potential Pitfalls Of The Hiking Date

Of course, there are some huge things you need to watch out for on a hiking date, I’ll try and let you know about the biggest pitfalls so you can avoid them.

Your Date Might Not Like Hiking

Many people just don’t like hiking. As hard as that might be to understand, many people didn’t have great experiences hiking growing up and that makes a huge difference.

A hiking date early on in a relationship is not the time to try and convince your date how awesome hiking is!

Always ask your date if they’re okay with a hiking date. It’s the least you can do to make sure that everyone’s on the same page.

If your date isn’t enthusiastic, you can always go for a stroll through a park. Visiting nearby botanical gardens or other similar sights are also fantastic outdoor dates.

Bad Weather

You start out on a hike early in the morning, but as it approaches noon, you start to see dark clouds headed your way. Uh-oh! now you’re stuck in a storm, you’re soaked through the skin, and you’re chilled to the bone.

Even the most meticulously planned hikes can go sour if the weather unexpectedly turns bad. That being said, always check the weather before you head out for your hike.

It’s always important to have a plan B for a hiking date so you don’t feel like you have to go.

Your Hike Was Too Hard Or Long

It took you hours of searching on the internet, but you’ve finally found the coolest hike around: an 8 mile loop that goes around the side of a mountain! You’re all ready to go, you checked the weather, and you’ve set out on your hike. But after over 2 hours of hiking, you and your date are exhausted and cranky, and you’re only halfway done.

When planning your hike, make sure you choose a hike that matches your needs and skill level. Hiking dates don’t have to be extravagant adventures to be memorable. In fact, even the 1 to 2 mile hikes can end in gorgeous views and great memories. If you do plan to go on an all day hike, just make sure you know what you’re in for, take breaks, and pack well.

If this is a first date, then this step is mandatory: Make sure the hiking portion of your date is only an hour long. This prevents the dreaded marathon first date. 1-2 miles is a great distance.

You Didn’t Bring Enough Food Or Drinks

You’ve planned your hike, chosen the perfect 4 mile trail, and the weather is predicted to be warm, but not hot. Everything seems to be perfect! But now, you’re 2 miles in and you run out of water. When you open your backpack to put your empty bottle back inside and grab a snack, you realize you left the granola bars sitting on the counter.

This couple forgot food and now everybody’s grumpy

Because you don’t want anyone getting “hangry” or dehydrated, make sure you bring enough food and water to last you trip. Even if you plan a sunrise hike and are going out for breakfast afterwards, make sure you bring something small to snack on, just in case.

Getting Stuck With a Creepo

There’s some unfortunate horror stories of hiking dates gone awry. It’s impossible to know what someone is like before a first or even second date.

The absolute worst thing that could happen is that someone may trespass your physical boundaries on the date, sometimes leading to disaster.

Things that could happen that are less worse is that you get stuck with someone who is very awkward and you’re far away from everyone else.

Fortunately, there is an easy fix to a hiking date if you’re concerned about the person you’re going on a date with.

How To Stay Safe On A Hiking Date

You want your date to go as smoothly as possible, so make sure you plan your trip well and follow these tips to stay safe on your hike.

Make It A Group Date

If this is a first or second date and your date is someone you don’t know very well, it doesn’t sound like the best idea to go into a remote location with a complete stranger!

Don’t fret, this doesn’t mean your date is crazy, it just means they love being outside. Fortunately there is an easy way to make this date much safer.

Ask your date if you can bring a roommate or other friend and make it a double date. Hiking makes for a fantastic double date because both couples can hang out together and have fun, or, both couples can give each other a bit of space so you can get to know your date.

If your date refuses a double date if you ask, then you might consider refusing the date.

Watch The Weather

Even the best-planned hiking trips can be ruined due to unforeseen weather. When planning your trip, make sure you watch local weather forecasts so that you don’t hike into a thunder or snowstorm. While a drizzle of rain can feel good on the hotter days, a downpour that causes you to take cover under a tree is no fun at all.

If you plan to hike the day after it rains or snows, check the reviews or comments of a trail to see if your particular trail gets muddy or icy. If this is the case, you may need to re-route your hike or choose a different trail.

Wear The Right Gear

Whether your plan is to hike on a paved path or deep into the wilderness, make sure your date knows that they will need active gear. While it may seem like a good idea to surprise your date with a hiking adventure, there’s a chance your partner won’t be properly dressed for such an active event.

By telling your date about the hike ahead of time, you’re setting your date up for success. If the weather’s cold, make sure you wear layers. You can always take layers off, but you can’t put layers on if you don’t have them. Equally important is footwear, so make sure your date has some sort of shoe that’s meant for hiking or physical activity.

For more information on what to bring on your hiking date, keep reading until the next section.

Know Your Trail

You never want to set out on a hike and find yourself walking in circles or lost in the woods, so make sure you know your trail before setting out. While it may be easy to rely on your phone or GPS, there’s always the possibility that technology will fail or you won’t have service, and you find yourself stuck between choosing left or right.

Before you leave for your hike, study the trail, know what turns you need to take/what trail you’re following, figure out some easily-spotted landmarks, and estimate how long you’ll be hiking. That way, you at least have a general idea of what to expect and won’t get lost.

What To Bring On A Hiking Date: Clothing And Other

There’s a lot of planning that goes into the perfect hiking date, so you definitely want to make sure you bring all the right gear and materials. So, what should you bring on your hiking date?

Besides your snacks, water, and other drinks, you want to make sure you have the right gear. When hiking, wear moisture-wicking clothing that moves sweat away from your body. This will help you stay dry and hopefully keep the stink away.

It’s also best to choose a breathable fabric, such as fleece, nylon, or polyester, and on intense trails or in extreme weather, avoid cotton.

If it’s cold, you’ll want to wear layers. To stay warm during the colder months, you should choose a moisture-wicking base-layer, an insulating middle-layer, and a protective outer-layer. Remember, you can always remove layers if you get too warm!

I’ve made a general checklist of things you’ll likely want to bring (and make sure you tell your date to bring) on your hike:

  • Pants, such as hiking pants or if it’s a short hike in good weather, jeans will work fine.
  • Thermals or a base layer (if it’s cold)
  • Jackets
  • Hiking boots (running shoes work just as well)
  • Sunglasses
  • Hat
  • Sunscreen
  • Bug spray
  • Lip balm
  • Map (paper or digital)

If you’re not sure about hiking pants, yourself, make sure and check out our article on hiking pants, or our article on hiking in jeans so you can be better prepared.

Furthermore, we talk about the difference between hiking boots, hiking shoes and hunting shoes here if you are considering buying a pair.

There’s a good chance your date won’t have any of these shoes if they don’t already hike–running shoes can do just fine for many trails–learn more about when running shoes are okay and when you need something more at our article here.

While the above list is more of a general checklist of what to bring on a hike, there are some other items you may want to consider, such as hiking poles, ice cleats, or snow shoes if you’re hiking in the snow. Some hikers also find it worth it to use a hiking GPS (see here for one of our articles that talks about whether a GPS is really necessary) to figure out where they are on their hike.

Choosing the best hiking gear can be tricky, so make sure to check out the links above to find out what gear is the best for hiking in the outdoors!

What To Wear On a Hiking Date?

Besides the advice I gave you in the previous section about making sure you’re layered properly and protected from the wind or rain, sometimes it helps to have more specific guidance.

If you’re hiking in 60-degree weather, then a light jacket with a t-shirt will work just fine.

If it’s 70-80 degrees weather then just a t-shirt and shorts, or an active skirt will work.

Jeans or long pants will also work but will be pretty hot in the 80-degree weather range. You might have heard that jeans are bad to hike in but this isn’t necessarily true. If your jeans are flexible and stretchy then this will actually work pretty well. If the hike is a long one, you might consider pants–but hopefully for a hiking date you’re not going very far. Learn more about hiking in jeans here.

If you want specific advice on hiking in 60-degree weather, check out our article, here.

If you’re hiking in cold weather, there’s a lot more to think about–I talk about this here for 30-degree weather..

How To Choose Your Hiking Destination

Figuring out where to hike can be one of the more challenging parts of planning a hiking date. Depending on whether you live in a city’s center or in a more rural area, you may have different options available. One of the most important things to keep in mind while you’re figuring out where to hike is what you want to accomplish.

I have an entire guide on how to choose a good hike, but here are some questions to keep in mind when choosing where to go on your hike:

  • How hard do I want this hike to be?
  • Do I want to go out and back, or do a loop?
  • How far do I want to go?
  • What do I want to see? An overlook? A lake? Wildlife?
  • Do I want to hike where there will be shade, or out in the open?
  • What are some popular hikes in my area?
  • Do I want to go on a busier trail or a lesser known trail?

If you’re a seasoned hiker, you probably have some favorite trails that you can’t wait to share with your partner, but if you’re new to hiking or exploring a new area, you may want to do some research before setting out on your hike.

Some great places to research your hike for any area include:

  • Google: when in doubt, using your search engine to find hikes near you will likely turn up many options for local hikes.
  • Facebook groups: most places will have local hiking and outdoors groups that have inside knowledge on the best local hiking trails.
  • AllTrails: this app lets you search any area for hikes, rates them for difficulty, tells you were to park, explains what you’ll see, and more!
  • National/State Park Websites: if you plan to hike in a certain region, the national and state park websites will have detail information on the hikes in the area.

Loop vs. Out-and-Back Trails

Typically, the two types of trails you’ll find will either be loops or out-and-back trails.

The loop trail is exactly what it sounds like: you start at one location, choose right or left, and complete a circle. For the type of trail, you’ll see everything once, so each sight will be unique. Depending on where you live, you’ll hike through forests, around lakes, or across open fields.

One thing I like about loops is that most people go in one direction, so even on a busy trail, people may not be hiking in your direction. Of course, if you’re going at a faster pace than others on the trail, you might have to do some passing.

The out-and-back, on the other hand, usually takes you in one direction to some sort of popular destination, most likely a look-out or gorgeous view. When looking at an out-and-back, definitely check out the detail of the hike so that you know what your destination is.

Depending on where you live, out-and-backs may end on top of a mountain, at a waterfall, or on a bluff overlooking the landscape. Because you arrive at your destination halfway through the hike, out-and-backs are perfect for a picnic lunch, sunrise, or sunset hike!

Although out-and-backs can climax at a breath-taking sight, there are some drawbacks. Because there is only one trail, everyone will be using that direction. You’ll likely run into people headed in your direction, or have to pass people if you’re going at a faster pace. Also, because there is only one trail, you’ll head back the same way you came and see the same landscape.

How Far Should You Hike On A Hiking Date?

The distance of your hike will depend on how long you want to hike. Although, keep in mind that the longer you plan to hike, the more planning your hike will require. If you want to get out for an hour, then you’ll really only need a water bottle and good company. But if you’re planning an all day hike, you’ll need to think about lunch, snacks, gear, and plenty of water.

When deciding how far you want to hike, the biggest thing to keep in mind is how much time you plan on devoting to your hiking date:

  • Do you want to go for a hike in the early morning and get breakfast afterwards?
  • Do you want to start after breakfast and finish in the early afternoon?
  • Do you want your hike to last the entire day?
  • Do you want to see the sunrise or sunset?

Generally, if you want to go on a hike that’s just going to take a morning or an afternoon, you should plan on a 2 to 4 mile hike. If you want to go on an all day adventure, plan on finding a trail that’s 5 to 8 miles long.

How Long Will The Hike Take?

Generally, you should plan for about 30 minutes for every 1 mile you hike. That means if you want to hike for only 1 hour, you should choose a hike that is around 2 miles total in length.

For loop trails, this is easy: the length is the entire loop. For out-and-backs, however, sometimes the websites and trail finders only include the length for half the trail, so make sure you confirm that your out-and-back is the total length you want, not just half.

Hike Distance:How Long You Should Plan To Hike:
1 mile20 to 30 minutes
2 miles50 min to 1 hour
3 miles1 hour and 30 minutes
6 miles3 hours
8 miles4 hours
10 miles5 hours
*the time you spend hiking will greatly depend on your hiking pace and your snacking pace

I have an entire article on how to pace your hike, so be sure to check it out if you want to learn more about how long hikes can take!

Most Importantly, Have Fun!

Now that you have the tools to plan your perfect hiking date, get out and enjoy everything that nature has to offer.


Peter is a software developer who loves to take every opportunity to go outside that he can get. Peter grew up going on long backpacking excursions with his family every Summer and now enjoys staying at the beautiful Texas State Parks and swimming in the amazing Texas Rivers.

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