If you’ve been keeping up with the musings of both myself and my fellow LiveOutdoors.com writers over the last two years, then you’ve no doubt read about how much fun fishing can be as a potential date. Not to neglect the trails, today we’ll take a closer look at how a trip to the woods can be a fun, creative way to explore a new relationship potential or even add some fun to an already existing one.

First things first: you should probably never plan a hiking date as a surprise. The potential for wardrobe mishaps is too strong and I’ll go out on limb to say that—no matter the girl—she will not be happy to discover you’ve planned a hike in the woods for your date if she’s wearing  skirt and heeled shoes. Sure there are women who are good sports about such things, and they can roll with things like that, but why risk it? You don’t want to start the date in the negative and not warning your date ahead of time to wear comfortable clothes and shoes they can get dirty is a sure step down that path. You don’t have to give away the fact that it’s a hike, but definitely give some advice on wardrobe.

When planning a hiking date, it’s also important to consider your date’s experience and fitness levels. Obviously, you don’t want to plan a 15-mile hike through rough terrain for a date with someone who doesn’t hike very often, if at all. If your date isn’t experienced, I’d suggest planning an easy trek along flat trails, without any treacherous hazards or demands. I would still try to get away from the hustle and bustle of city life, though, if possible.


If your region permits, it’s a great idea to plan the route to take you along some rare or scenic views at a various points. Not only will this be a unique way to expose your date to some things they might not have ever seen, but you’ll be able to share in those moments together, which is a great way to establish some exciting memories early on. Furthermore, take advantage of these opportunities to engage in conversation with your date. Whether it’s a first date or you’re years into the relationship, conversation is a crucial part of the equation, so take advantage of those moments when they present themselves.

Lastly, you’ll want to decide ahead of time if you’ll be bringing food or waiting until after the hike to go get something. I tend to opt for the picnic meal, for two reasons: it’s more fun, and no one wants to have to go to a restaurant if they’re sweaty or muddy. Also, if you really want to be creative and thoughtful, it can be great to have a picnic waiting for you at a specific location ahead of time. This will solve the meal problem and it will also show your date that you’ve planned ahead and put a lot of thought into the date, which she’ll love!

There are a few other details to consider, as well, such as bathroom availability or weather, but if you’re able to gauge your date’s experience and plan the date accordingly, it shouldn’t be a problem. As far as the weather is concerned, that’s one thing you’ll never be able to control, so it’s smart to have a back-up plan. Hiking can be a great way to get to know someone early on in a relationship because it’s fun, creative, engaging, and also allows you to see how open a potential partner is to sharing an important part of your life with you. Keep the aforementioned tips in mind and you’ll be off to a great start!