Hiking with others is usually the safest way to go, and if you're in good company, it can actually be a lot of fun. But what if you don't have anyone to hike with? You could join a hiking club or a hiking Meetup group -- or just "grow your own" by talking a friend into hiking with you.
If you take a friend hiking you want him (or her) to have a good time (and get hooked so he'll want to go for more hikes), right? A little ahead-of-time preparation and consideration will do a lot to make sure you leave your buddy wanting more time on the trail with you.
- Discuss expectations beforehand. Are you both on a mission to reach the final destination, or would you rather just ramble? Is there anything he really wants to see (like a hike to a lake, or a trail where you're likely to run into certain wildlife)? Seeing as how you want him to enjoy this new experience, you might as well cater to his desires.
Help him pack. Hold a casual conversation about hiking gear beforehand, and give him a list of things to bring. You get extra buddy points if you can provide any of the gear for him and if you're willing to carry it at least part of the time. (On short hikes, a single daypack shared between two people can carry all you need.)
When it comes to the items he should bring, like footwear, be specific (lest he show up in flip-flops or mountaineering boots). And on the day of, double-check that he has critical items (Water? Extra layers?) before you leave the house or wherever you'd decided to meet up.By the way, speaking of footwear: Make sure he's broken his boots or shoes in beforehand. Even if you're going on a short hike, wearing his boots around town for casual errands for a week or two first will help them form to his feet and reduce his risk of blisters.
- Brief him on potential hazards beforehand. No need to scare him off, but do make sure he knows what to do if he encounters any likely hazards on the trail. Examples include how to handle bears, moose, mountain lions, snakes, or whatever other wildlife you're likely to encounter in your area. If you're going to be on steep, rocky terrain, teach him to yell "Rock!" if he dislodges something, and to keep yelling it: "Rock! Rock! Rock!" until the object has stopped moving or no longer poses a hazard to others. That way he'll know what it means if he hears someone else yelling the same thing.
- Smuggle some comfort items along. No need to nanny your friend, but having extra snacks or water along at just the right moment would make any hiker happy.
Choosing a Trail
- Start with a short hike. Being out longer than you expected (or are prepared for) can turn even the best hike into a footsore slog, so play it safe by starting with a hike that'll leave your friend wanting more (instead of wishing it would all be over with). With that being said, let your friend's fitness level and expectations rule the day. I consider a two- to three-mile hike to be the sweet spot for starting out, but if he's only up to half a mile, hike for half a mile. If he's in great shape, wants to go for a long hike, has well-broken-in footwear and you know it's well within his capabilities, I say go for it.
- Choose a trail you're familiar with. This eliminates oh-so-many potentially embarrassing and inconvenient issues, like getting lost on the way to the trailhead, underestimating how long it'll take to do the hike, or not being sure which way to go at forks in the trail.
- Make sure he knows where you're going. That way, on the off chance he has to call for help, he'll be able to describe your location. While you're at it, make sure he knows how to signal for help. No need to make this scary or overly complicated; just give him an emergency whistle and tell him that three short blasts means "SOS" or "Help!"
This might seem like a lot to think of beforehand, but it really amounts to just a few minutes of packing and discussion. After that, you're ready to hit the trail and enjoy.
By the Way...
One last detail. If you really want your friend to remember the hiking experience fondly, take him out to a hearty dinner afterward. Returning him to his house or car with a full belly can erase any multitude of mishaps on the trail. Even if the hike was great, he's probably worked up a well-deserved appetite -- and the warm glow of satiation will make him remember the entire outing that much more fondly.