We’ve all had that moment where we stare out of our office window thinking about how long it’s been since we last experienced natural light and fresh air. We sigh, shake our heads, and go back to clearing through our inboxes. But wouldn’t it be great to just leave it all behind and spend your days in the great outdoors? Someone out there has that dream job. But who?

After a long day on the trails, we sat down with Mike D’Anniballe, the head guide for Hike With Mike NY, at a local watering hole to talk about getting paid to take urbanites up and down mountains in upstate New York.

How did you get started giving trail tours?
The summer between when I graduated high school and began my first year of college, a friend invited me on a trip to climb the highest mountain in Maine: Mt. Katahdin. He totally undersold me on the distance and difficulty of the trip to get to the mountain and the hike itself. It ended up being one of the most difficult, arduous, frightening experiences of my life, but the feeling I got standing at the top of that mountain was nothing like I had ever felt. Without his support and encouragement, I could have never gotten to where I was standing. These two things are at the core of the outdoor experience and have all but defined my life since that moment: companionship, the sharing of a unique experience, the bond that is born from that sharing and the intangible, fleeting feeling of accomplishment of a goal that you had previously thought impossible.

Trail guide

I could probably hike on my own — why would someone need a guide?
We take care of everything for you: Directions to the trailhead, recommendations on appropriate gear and clothing for the particular adventure, delicious food. We know these places intimately—in terms of their natural and cultural history, their hidden secrets that you most likely would not find on your own—from years of experience and research. Third, our knowledge and enthusiasm help you to have a better experience with the time you have available or the goals you have in mind. And finally, if anything were to go wrong, we’re there to not only fix the issue but to help make the best of an otherwise ugly situation. Most of all, you want to come out with us because we love what we do, want to share this love with the people that come with us and will go to almost any length to do so.

What’s a common mistake first-time hikers make?
Wearing cotton. When you hike you sweat, and when you sweat your clothes get wet and when your clothes get wet you get cold. Cotton soaks up perspiration doesn’t allow it to evaporate and dry. Wool and other synthetic materials are a much better choice for hiking.

I get to share a unique, beautiful experience with others. Guiding has given me the opportunity to kick a door of possibilities wide open.

Who’s your typical client?
Our typical clients are folks from the city who are looking to get out for some fresh air and adventure or a night out under the stars. They can be folks who have no experience in the outdoors as well as the more experienced people who just want to keep it simple and enjoy the benefits of having a guide.

Taking a selfie break

Do you have any favorite hunting gear?
Most important of all are your shoes. Everyone has a different preference and need in their footwear. Folks always ask which is the best footwear, and my answer is always choose whatever works best for you. For my own feet I prefer those new weird Vibram FiveFingers, but others need to go with a sturdier more supportive boot.

Vibram FiveFingers
Vibram FiveFingers, Mike’s preferred footwear for hiking.

The second most important part of your gear is your base layer; socks, underwear and shirt. This is what you wear next to your skin and is the cornerstone of comfort for the outdoorsman. Stay away from cotton and stick to synthetics silk or wool. I know it sounds like a bad idea to wear itchy wool next to your skin, but companies like SmartWool and Darn Tough are doing amazing things in the processing of wool to make it the pinnacle of comfort for outdoor sports.

Another indispensable piece of gear is your backpack. A good outdoor pack has lightweight-but-dense foam shoulder straps and, most importantly, a padded hip belt. Almost as important as the quality of the bag is its fit on your body. For help with this seek the advice of your local outdoor retailer or guide.

Is there an item you can never hike without?
I always, including in the summer, have some kind of head covering with me, whether it’s a hat, a repurposed neck warmer, a Buff, a bandana, or even a zip-off pant leg. It’s great in the winter for warmth, and useful in the summer for sun protection and keeping sweat and bugs out of your eyes.

If someone was interested in becoming an trail guide in their area, what advice would you give them?
You not only need to spend time outdoors, you also need to spend a significant amount of time in the area you plan on guiding in. You can read a trail guide or a book about local plants and animals, but without hiking the trails, smelling the flowers and hearing the animals you don’t really know anything about them. Your personal experience teaches you what not to do so you’re better prepared when you have have clients with you.

How has technology changed your job? I imagine it’s tough to get great cell reception in the back country.
I love having all of that information at my fingertips, but there’s also something to be said about leaving it all in the car and going out on your own with basic tools like a map and compass. My phone takes care of the minutiae such as distance tracking, photo snapping, route planning, and navigation. I’m able to devote more attention to the client experience. I’ve had technology save my skin more than once.

As a hiker, I choose to leave a lot of these advantages behind. I prefer a map and compass to my GPS on steroids. I prefer my visual memories and emotional impressions to photography. I prefer being in the dark about how far I am from the top of a mountain until I’m just stepping up to it.

Technology is useful, but it can cause people to become artificially comfortable in a wild setting and can lull them into complacency when it comes to developing a solid foundational set of outdoor skills. I never recommend them in place of learning things the hard way when it comes to beginners.

How many people do usually like to have in a hiking group?
Six to eight is the best size for a day hike because it gives everyone a chance to socialize and keep conversation fresh. For overnights, I always like a tighter group of between 3 and 5. The scope and potential is much different than a day hike and the solitude and quiet you get in the woods in the dark is an unbelievable experience that’s difficult to attain with a larger group.

What do you look for in an ideal campsite?
A nice, flat area big enough for the tents the group will be sleeping. Sleeping on a slope is a sure fire way to ruin what should otherwise be a nice restful night. Next is proximity to a water source. You’d be shocked at how much water goes into cooking, cleaning, drinking and washing. After that I go for solitude. The last thing you want is to hike 10 miles into the middle of nowhere and have to hear other people making noise while you’re trying to enjoy the sounds of the forest at night. And finally, beauty. You want to wake up and be surrounded by the most beautiful, calm scene you can. This can be different for everyone so with a group make sure to take everyone’s opinion into equal account.

Is there anything you wish someone had told you before you started guiding?
Guiding is what I should have gone to college for, studied business for, traveled the world for and lived my life toward the 30 years prior to starting Hike With Mike. I love the prospect of turning my passion into my life’s work and the opportunity to share my love for the outdoors with others.

For more information on Hike With Mike visit www.hikewithmikeny.com