The Beginner’s Guide to Planning Your Own White Mountain Hikes

I posted on Facebook recently that “Apparently ‘teach people to do their own hiking route-planning’ is the windmill against which I have chosen to tilt this summer.” I was halfway kidding, but only halfway. I follow a couple of local hiking groups in which people are constantly asking, “Which mountain should I hike tomorrow? What route should I use to hike it?” and it makes me a little crazy because for me, part of what makes hiking fun and keeps it engaging over time is being able to pick and plan my own routes.

I understand why that can be an intimidating thing if you’ve never done it before! But it’s not actually a hard skill to learn. So I’ve put together this little five-step guide for anyone who wants to try it out.

  1. Stop worrying and learn to love random choice.

Here is the big secret about the question, “What mountain should I hike next/first/last?”

The answer is, “It doesn’t matter.”

It really doesn’t! Or rather, it doesn’t matter much. There are some very basic criteria that are always smart to keep in mind, especially if hiking is a new activity for you.

  • Try not too bite off more than you happily chew, distance and difficulty-wise.
  • Don’t go above treeline in poor visibility or during an electrical storm.
  • Avoid water crossings when the rivers are running high and fast
  • Stay off the difficult scrambles if they’re icy or wet or likely to become so later in the day.

Best practice is always to cross-reference your plan for the day with the White Mountain Guide so you’ll know what to expect and then seek out additional resources as needed to clarify, “How’s that water crossing?” or, “Will I be sad if I try descending this trail in the rain?” I’m not going to cover those resources here. For purposes of this post, just know that they exist.

But outside of those parameters, it genuinely does not matter much which mountains you hike or what order you hike them in. So just pick something. Whatever is closest to you or farthest away. Whatever your finger lands on when you point randomly at your map. Whatever name appeals to you most or whatever strikes your fancy. Zealand intrigued me long before I ever hiked it. I have no idea why, but to this day that mountain and the area around it feel more like home than anything else in the Whites.

It doesn’t matter. It’s going to be fine. Pick anything. Read a little about it. If you don’t like what you read, pick something else.

And if you just need somebody to tell you that what you picked is a fine choice, then shoot me a message on Instagram and tell me all about it. I’m not an expert in every trail and I’m not very swift in responding to comments here, but IG is easy from my phone and I’m happy to play sounding board and reassure you that, “Yes, Pierce from Mt. Clinton Rd is a lovely first choice,” or, “Maybe Osseo would better than Flume Slide if you’re worried about your dog.” Seriously. Standing offer.

2. Follow the leader.

You can even start route-planning by not route-planning. One of the nice things about hiking the Whites is that the popular trails to the popular mountains are really well-documented. I recommend the Steve Smith book and also this website. Once you have your mountain picked out, both will help you figure out how to get there. There’s nothing in the world wrong with hiking the easiest and most popular routes, especially if you’re new or building confidence. Again, cross-reference with the WMG. Then go ahead and follow all that good advice that’s available to you. Enjoy!

The other option here is to have or make hiking friends who are willing to take charge of the planning department and follow them around. Ask  them how the picked the route that they did and what options they’d considered but discarded and why. They’re doing you a service, so maybe offer to feed them now and again. In retrospect, I owe some folks some food.

But if the first step of doing your own route-planning is to listen to someone else’s route-planning, that’s okay. You have to start somewhere and that’s as fine a place as any other. As you’re hiking it, look around. Check out the signs at the junctions and look down from the summit to get ready for…

3. Same destination, different journey.

So now you’ve hiked some stuff. You know you enjoy it. Maybe you even have a favorite mountain or two. Great! Now think about what caught your eye the last time you were there. Was there a trail you crossed that looked interesting? Did you glance down the opposite side of the mountain and think, “It looks pretty down there?”

Grab your maps. Grab your Guide. Where does that trail come from? Where do you need to start to get back to that junction on the way to the top of your mountain? What is down in that valley and what would you need to do to see it for yourself? Figure it out and then give it a try. Congratulation! You’ve planned your first route.

One of my favorite hikes last year was an out-and-back to Spaulding Lake. That hike was motivated entirely by hiking along the shoulder of Mt. Washington looking down into the Great Gulf and feeling curious about the little blue spot that I could see way down below me. Likewise: on my list for this year is Carrigain via Desolation trail because of the time that I stood in the fire tower thinking, “Wow, I really hated the Signal Ridge approach but that side looks beautiful!” I don’t know yet what I’ll think of that side, but I’m excited to find out.

4. Looking at maps.

Lots of people only ever hike 4,000 footers and if that’s you, that’s fine. But there is plenty else to see in the Whites — some of it on the way to higher summits and some of it worthy for its own sake. After you’ve sparked your curiosity in real-time by picking out new things to try while on trail, the next step can be sitting at home on a rainy day (like today) and getting curious about the maps that came with your WMG.

In some ways this is just step #1 again, but with more confidence. What looks interesting? What names and fine prints catch your eye? Which do you remember from friend’s photos or from other people’s posts in your local groups? See those little stars that indicate scenic views? What happens if you string a few of those together until you have as much or as little mileage and challenge (look at the topo lines and your WMG) as you want for the day?

This can be a great way to give back to those hiking buddies that shepherded you along in step 2 or to new buddies who want to join your adventures. I recently took a relatively novice hiker up Madison for the first time; I knew from previous hikes that they were fit, game, and capable and I had been eyeing some scenic view stars, so we ascended via Howker Ridge instead of Valley Way; time will tell if that planted any seeds.

This can also be a great way to avoid big crowds on popular hiking days. This strategy has led me many times to depart from overflowing trailheads and then not see anyone on trail for hours. It is my very favorite party trick. (I might be doing parties wrong.)

This strategy and the gems it uncovered was also my gateway to redlining, which brings us to my final step…

5. Hike all the trails.

Yep. After a few years of describing my weird, gorgeous hikes to nowhere as joyrides, I have reached acceptance. I’m officially redlining now. That means I’m trying to hike all the trails in the White Mountain Guide. I’m only a bit over 22% done as of now, so this is my hobby for the next couple of years.

Step #5 is not actually “start redlining,” unless of course you want to. Step #5 is just, “Start hiking more trails for the sake of hiking more trails.” If you love Franconia Ridge, try to approach it from every possible route and direction. If you love the Wild River Wilderness, load up your backpack and hike it the whole way around. What does Isolation look like if you hit Crawford and Stairs on your way in? Beats me, but I hope to find out in the next month or three.

Sometimes hiking a new trail just for the sake of hiking a new trail is less rewarding than you might hope. But often it’s more. It turns out that the prettiest part of the wildly popular Alpine Garden is the two-tenths of a mile that almost no one hikes. And now that every trail is in play for me, I’m starting to look at the maps in a new way, not just for the trip that I’m planning today but also for how other future trips fit alongside it. It’s like seeing into a new dimension. It’s the most exciting thing to happen to my hiking since my first 4,000-footer.

Which was Waumbek, by the way, in a pouring early June rain. So if you’ve read all this and you still want to know which mountain you should hike first, next, or last? The answer is Waumbek.

Just make sure you peek a little farther down Kilkenny Ridge and save a picture in your mind for the future before turning for home.

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