The Ultimate Hiking Proposal Guide

There are plenty of great proposal locations, but if you and your special someone are outdoorsy types, there’s really only one perfect place to pop the question: at the end of a grueling five mile hike through woods, over streams, and up the side of a mountain, to an overlook with 20-miles visibility and the forest spread out like a carpet below you. The hike to this (or any) scenic masterpiece will get your blood flowing, and flood your body with endorphins. It’s exactly the state you want to be in when asking another person to unite with you in a legally, financially, and emotionally-binding joint venture like marriage.

The Decision:

So you’ve decided to pop the question while hiking. Outstanding. But which trail are you going to take, both figuratively and literally? You can’t just drive to the nearest trailhead and start walking. This is not a casual walkabout: this needs to be strategized. If at all possible, check out the location firsthand.

First off, this hike has got to fit the occasion. It needs to be enough of a challenge that, by the time you get to the proposal location, the two of you are filled with a sense of accomplishment and pride. Just reaching that spot should feel like something memorable, a story to bring out in the future, when you and your hiking friends are remembering old adventures. You want her to feel like nothing could possibly top that moment—and then you proceed to top it.

We said challenging, not difficult or extreme. You don’t want to arrive at the proposal spot and be too tired to move. You want her legs to give way from joy, not from heat cramps. You also need to, presumably, walk back.

Don’t pick just any challenging trail either. Go for one that has some sort of relevance to your relationship, somewhere you’ve hiked before, or have always talked about hiking. Does the view from your chosen spot overlook the town where she grew up, or the lake where the two of you met? Even better. OK, you’re set.

The Pros: Beautiful weather, mountain air, lots of trees, physical exercise, high probability of privacy, no need to wear a suit.

The Cons: Miserable weather, accidents, allergies, even the remotest possibility that she’ll say no and you’ll have to hike home in an awkward silence.

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How To Plan:

A hike is an outing all on its own, so you don’t have to come up with a plan to get to a particular time and place. She’ll naturally help you in getting everything together for the day—boots, water bottles, trail mix, etc.—which will give you extra time to secure the the ring and practice your proposal.

How do you plan the proposal itself? Very carefully. There are plenty of things to watch out for while hiking (see below), and none of them are made any easier by the knowledge that you’re packing several thousands of dollars worth of engagement ring in one of the pockets of your windbreaker. Drop your water bottle down a cliff face by accident and you can always just buy another one when you get home. Fumble that ring box and you’re going to have to go looking for it at the bottom of the cliff. And you’ll ruin the surprise.


Engagement ring, Swiss Army knife or multi-tool, water and energy bars, a tent (if you plan to camp after).

What To Watch Out For:

Photo by Dylan Furst

Going for a modern day hike, even a challenging one, is not generally a dangerous proposition. With GPS, rescue helicopters, and National Park Service employees in the area, you’re probably not taking a huge risk by heading off into the wild That said, it IS more dangerous than going to a nice Italian restaurant to pop the question, or bringing out a ring at the top of the Empire State Building.  Be sure to watch out for…


They may seem picturesque and charming, but rivers can be vicious sons of bitches. Always try to find a bridge or some other way of crossing, even if the water looks completely wadeable. Rivers have currents, and these can sweep you under the water—even if it’s only waist-high—before you know it.


Lightening is the sky’s way of handing out smackdowns. If you’re hiking up a mountain, you may be more exposed to a random lightning strike (remember, you’re carrying an engagement ring made out of precious metal, and metal is a great conductor).  Check the weather report before you leave, always keep an eye out for storms, and if they hit, try to find appropriate shelter. Said shelter does not include tents, caves, or trees: standing near or under a tree during a thunderstorm is asking to get flash-fried. If you’re on the elevated part of a trail, turn around and head downward: the lower you are, the better.

Freezing To Death

Hiking in the cold can be fun, but dress accordingly. Remember that it may be several degrees colder at the end of your trail than at the beginning. Signs of hypothermia include clumsiness, blurred vision, slurred speech, and, paradoxically, warmth. You want her to get that warm feeling from love, not from her organs shutting down.

Sweating To Death

Warm weather hiking is more common, but it has its risks as well. You don’t want either one of you to get heat stroke on the way to your romantic moment, so don’t skimp on the hydration. Your first engaged kiss should not be with dry lips, nor should your fiancée’s racing heart and rapid breathing be the result of anything other than excitement.

Lions, Spiders, and Bears

Nature is full of creatures that would like nothing better than killing you and your bride-to-be, so avoid mountain lions, black bears (any bears, really), huge snakes, and poisonous insects (such as the bullet ant, the tarantula hawk, or the giant desert centipede). Fortunately, most animals are not idiots: they know us people are more trouble than we’re worth, and will actively try to avoid us.

If, however, you have a run in with an animal, don’t think it’s going to go easy on you just because you’re on the way to propose to your sweetheart. A mountain lion is not, generally speaking, sentimental. But it respects strength, so don’t run away from it. Maintain eye-contact, wave your arms and make noise, and even throw sticks at it if you can. Maintaining eye contact is usually a pretty good way of intimidating animals (except if you’re attacked by a grizzly bear: grizzlies don’t play that.)

Taking The Plunge (Off A Cliff)

Doing something you love with the person you love is a wonderful feeling, but that doesn’t mean you can just prance along the trail like you’re in a Disney musical. Keep an eye out for falling stones, tree roots in your path, and sudden drops that can send you tumbling down a mountain.

Stray Gunfire

Be aware of hunting season, and make sure you’re not wandering through a place where people will be firing shotguns or bow hunting. It never hurts (other than the eyes) to wear some bright orange.

Losing The Ring (Waterfalls)

We’ve talked about waterfalls and proposals before, so all we’ll say here is that waterfalls are to be avoided when proposing. We also caution you not to take the ring out in windy weather, in rain, or while crossing one of those rivers (which we told you not to do anyway). Remember, you’re going to be nervous, and you may very well drop the ring. If recovering it would require anything more elaborate than bending down and picking it up off the ground, keep it stowed. Wait until you’re in a safer place before revealing the ring.

Poison Ivy and Ticks

If you have any experience hiking, you’re already looking out for these guys. The point is, you don’t want her showing off her ring on an arm covered in peeling skin or bullseye rashes.

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What To Do:

This depends on where you’re hiking, of course. If you’re headed to the top of a mountain, you can show her the view, say “I wish I could give you everything you see before you, but for now I can only give you this rock,” and bring out the ring. But did you really walk that far to be that cheesy? Don’t try to fit a metaphor into the situation: it’s compelling enough on its own. Just say something direct, heartfelt, and romantic, get down on one knee and say “Will you marry me?”

What Happens If…

It rains

If it rains, you’ll get wet. Assuming no lightning is involved (see above), rain can actually be quite romantic. Did you bring a tent? There’s nothing like the patter of raindrops on canvas to set the mood for a private proposal.

You both get too tired, and turn around

No problem. Find a picturesque diner and propose over a plate of mashed potatoes. It will make a good story, and she can call her mom right away.

You encounter a “Deliverance” type situation

A life-or-death struggle with hostile backwoods types is actually one of the best proposal scenarios there is. The two of you will be stripped down to the core of your beings, tested by a white hot crucible of terror and rage. You will be mentally and physically driven to the extremes of endurance, transformed from a modern day, civilized couple into a pair of savage animals engaged in a kill-or-be-killed fight for survival. It will be a very bonding experience—if you both survive it.

Bottom Line

Proposing during a hike is a great idea—but it’s not for dilettantes. Take the proper precautions before hitting the trailhead, and you should be fine.

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