Hiking with kids is always an adventure. But, is it a challenge? Can taking a hike teach your children problem-solving skills, creativity, ingenuity, and grit? Have you ever purposely taken a hike to get off the beaten path in order to encounter obstacles? That’s just what today’s post is all about! Jared Ryan, Oklahoma dad of two is here sharing his family’s experience with Roosevelt walks. Inspired by President Teddy Roosevelt, a Roosevelt walk is an intentional hike where, when confronted with an obstacle, you must go over, under, or through it…never around. These walks can be quite an adventure and lead to teaching kids skills and values in new and creative ways. 

Hiking with Kids - The Roosevelt Walk

A new spin on traditional hiking

Have you ever found yourself looking for ways to boost your kids’ enthusiasm for hikes? One of our family’s favorite activities, regardless of the season, is to go venture out onto a hike. Our kiddos always love it. They have tramped hundreds of miles and have worn through countless pairs of little Merrells. From hardpacked clay, tough granite rocks, or supple loam, they’ve hiked it all. Needless to say, sometimes my wife and I are tasked with trying to change things up on them in order to make sure they still experience that wonderful feeling of adventure when we step off the concrete and into the wild. Our favorite way to spruce up the average hike is by doing what we have dubbed as the ‘Roosevelt Walk’. 

Teaching kids how to overcome obstacles when hiking - Roosevelt Walks

The inspiration behind the hike

The 26th president of the United States, Theodore Roosevelt is known for his deep love of nature and his establishment of our National Parks system. But, he is quite possibly equally know for his relentless pursuit to maintain a ‘strenuous life’. So much of a pursuit, in fact, that within his first year of presidency, reporters associated ‘strenuous’ with his name over 10,000 times. Yeah, for real.

When Teddy wasn’t rustling cattle in the North Dakota Badlands, leading expeditions through the Amazon, or lecturing lawmakers in Washington, D.C., he was leading his six children on walks around Sagamore Hill. (Six!) In true T.R. fashion, Roosevelt had one primary rule for the hikes though:

When faced with an obstacle in their way, the family could only pass it by going: over, under, or through it… Never around it.

Roosevelt Walks: Hiking with Kids -Get off the beaten path

What is a Roosevelt walk?

And so we started taking what we called “Roosevelt walks” – hikes where we could go over, under, or through our obstacles. When we hiked, nothing would stand in our way… or maybe it did, but we’d have to find a way over, under, or through it. Our kiddos (and my wife and I) quickly learned that these Roosevelt walks are, well, amazing. I mean, distance no longer matters, and the terrain hardly matters. In fact, the further away from a smooth, well-worn path, the better. I feel that I should also let you know that these short, adventurous hikes are often far more tiring and grueling than a longer stroll on your average trail. After all, you aren’t taking the easiest route.

Where can you Roosevelt walk? 

Roosevelt walks can be done nearly anywhere. But, if you find yourself squirming a little at the thought of leaving a marked trail, no worries I do too sometimes. We have actually found ourselves doing our Roosevelt walks both on and off of trails. A lot of trail networks offer the same geodiversity on them as anywhere off of them. So if this is the case for you, your preplanning may have just gotten a lot easier. When the terrain surrounding the blazed trail is calling for you, there can be a whole new world (cue Aladdin theme song) opened up in even your most familiar parks and trails just by stepping off the beaten path and working through unfamiliar obstacles.

*Certain trails and parks do require that you stay on the trail, so make sure and check the trailhead or park office for guidance. 

A new spin on hiking with kids - how to overcome obstacles and teach grit (Roosevelt Walks)

Why you (and your kids) will love it

To me, the dad, there is a never-ending search for ways to show my children how to navigate life. How to problem solve, how to persevere and overcome. To keep myself from inhibiting this process I simply:

  • Allow my little teddys to come up with their own strategies
  • Refrain from mitigating the difficulty of the situation
  • Follow along with their lead and let them be in charge of the situation

Feel free to add additional wrenches to your hike as well. When we are exploring on our family land, I like to reach a point where the kids are not quite sure where we are and then allow them to navigate us back to the cabin. This has taught them new navigation skills along with building their confidence in making decisions. When coupled with our Roosevelt walk, these <1mi hikes can take several hours, but my kids have never complained. Sometimes they get lost on the way, and that is fine, but usually, they’re lost in their thoughts on the task at hand. And that’s perfect.

It’s absolutely satisfying to me watching them ascend a vertical rock wall that is tip-toe height for them or weave their way through the branches of a felled tree. It’s almost like their confidence is visible and you’re watching grow in real-time.

For parents: these obstacles usually bring the same feeling of accomplishment and a boost to our confidence. We all know how quickly and easily we all get so caught up in our infinite emails and our daily Teams meetings and that no matter how hard we resist the mundane. We start to lose that internal feeling of overcoming something, of perseverance, of strenuousness. So, when you have overcome that blocker on the trail or when you’ve faced your fear of what’s new and unknown, you also get to feel a little proud, just like your littles. Plus, you will most undoubtedly use muscle groups that you may not have used since the last time you played tag on the grade school playground. 

Working through the barriers as a family always builds our team closer. Because we’ve overcome something together and we collaborated on it. Although, honestly, I usually let the kiddos give their input and I often just go along with their strategy. In my mind, it’ll either work, or it won’t. Either way, they’ve learned something new. 

Keeping it safe

To be real, there are definitely times that we do come across obstacles that could put us into real danger. Not just thorn briar danger, but proper emergency room danger. This just is NOT what these hikes are about. When we’ve stumbled into a situation like this I simply explain it to the kids. The purpose of the hike and why it’s okay that we’re rerouting. I mean seriously, my son is far too willing to try and hurl his 4’0″ frame across an 8ft gap. So, I do have to reign them in.

To this point on dangerous situations, my wife and I try to plan ahead in order to find locations that will allow us to safely roam and ramble with consideration of the type of terrain and the time of year. When venturing out, we always have an idea of where we’re going, what we are getting into, and a sense of the severity of any situation.

Where we live, in the central United States, we know the following truths:

  • There is a venomous snake in every brush pile during the summertime (at least in our heads).
  • Loamy woods are much more forgiving after a rain than the slick sandstone bluffs.
  • Creeks that are dry in February are deep and flowing in April.
  • Poison oak leaves look a heck of a lot like normal oak leaves.
  • In July, whatever water you brought isn’t enough.

Regardless of how intense or how chill your family’s version of the Roosevelt walk is, make it your own. Roosevelt walks are such an easy way to bring some fun and excitement to your short hikes.

Keep your eyes on stars and your feet on the ground” – Theodore Roosevelt

Have you ever heard of a Roosevelt walk?
Are you ready to give them a try?

About the author

Jared is a husband to a talented and beautiful wife, Kristen, and a father of two fun-loving and adventurous kiddos. He enjoys leading family adventures to both near and far destinations. Whether it is hiking, camping, climbing, bike riding, or playing in the backyard, he loves it all. He instills in his family the importance of nature and all the benefits it can bring to one’s life. Jared is a GIS analyst by trade, so he is naturally drawn to creating maps and all things trail related, whether it is creating new trails, recording family hikes, or teaching his kids land navigation, he loves to tie in his own work with family adventures.

You can find Jared online in the following locations:
Instagram: @bikeshikesbiners
RWMC posts: Jared Ryan