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Backpacking the Strawberry Wilderness: 8 Insights to Living Your Best Life On & Off the Trail

It had been many years since I last spent multiple nights in the backcountry hiking and camping in wild places that most people never see or experience. It had been so long, I had forgotten how much I loved it. I had also lost touch with how immensely worthwhile all the planning and preparing for this type of adventure is once I took my first steps onto the trail and I felt the last vestiges of the pre-trip jitters seep like water through the interlaced fingers of the dusty earth under my boots.

Strawberry Wilderness was our backup plan. It wasn’t our first choice, but it ended up being our best choice by far. Our first choice was to circumnavigate the Three Sisters mountain range in the eponymous wilderness area. By departing in August, our goal was to avoid bugs, mostly mosquitos, and give plenty of time for the high-mountain snow to melt following our winter of El Niño snowfall this year. We accomplished that but left ourselves open to August’s most dominant threat in the Pacific Northwest—smoke. With fires raging around Central Oregon, we shifted our focus to where the air was clear, which was right outside of Prairie City, Oregon, four hours east of Bend.

Fortunately for the seven of us on the trip, our dear friend Joy, planned all the logistics. She took the lead for several reasons that all seemed obvious and delightful to the rest of us. Firstly, she loves operationalizing a plan of action, and she’s great at it. Having just been there two weeks before on a shorter trip with her daughter, she had a clear idea of how to plan our route for maximum enjoyment and minimal risk. She accounts for what can go wrong and plans proactively, leaving me feeling confident we were in great hands. Additionally, as the Queen Gear Guru, Joy had a sound, well-researched and tested opinion on most essential gear that would take the newbie backpacker (or a very rusty one) from wide-eyed neophyte to sure-footed backcountry goddess. With the question of what gear and what to do with it covered, seven of us girlfriends loaded our 55-liter packs weighing between 25-30 pounds each (mine crested 32 pounds, but it still felt very manageable).

On Saturday morning we navigated the last road to the trailhead of Strawberry Wilderness at 12:30 pm with packs stuffed, poles accessible, and only last-minute adjustments yet to be made. I had eaten the hummus sandwich that I packed in my lunch cooler well before the dirt road devolved into a series of sinkholes that my friend Cherith deftly navigated by shifting her Ford adventure van into four-wheel drive. I grabbed the handle at the sliding door, hooping and hollering, enjoying the feeling of my bobbing body on the choppy waters of the road. I felt giddy and playful, my pre-trip nerves liquifying with the jostling of the van into an eagerness to be unleashed onto the trail.

We unloaded and made our final adjustments to our packs. I took a photo of my pack, admiring the tightness of the package it created, noticing the shine of the nylon pressed like a balloon about to pop. The sound of pole tips on gravel mixed with grunts as the seven of us hoisted our bags onto our shoulders. I clipped my hip belt, cinching the weight of the pack onto the iliac crest of my hips like Andrew at REI taught me when I was there the day before trying on packs. I clipped my sternum strap on my chest and tugged gently on the straps over my shoulders causing the top of my pack to bend in toward my body. I had made myself into a turtle, and I spun around slowly to appraise the snug fit of my shell to my back. Pleased I joined the group gathered at the trailhead waiting to begin.

On our first afternoon on the trail, we hiked 4.1 miles to Slide Lake. The trail was challenging with exposure as we traversed and climbed the steep mountainside while getting used to the weight of our heavy packs. Our first evening at Slide Lake, we cooled off by skinny-dipping in the clear lake as the sun was softening its grip on the day. White mountain goats galloped to the edge of the lake as we sat drying off after our swim. They dipped their noses to the water adjacent to where we were camped, a baby goat trailing his mother to our delight. We toasted to our friendship and our shared wisdom in choosing to spend our time together in this special place as the sky transformed into golden brushstrokes of pink and orange.

We lingered in camp the next morning, allowing ourselves the luxury of living free of the burden of time. Each in our own time hiked well past camp to locate our food bags hanging high off branches overhead. We gathered by the lake’s edge and sipped coffee, marveling at the white specks of goats high on the cliffs beyond the lake. We warmed ourselves with oatmeal and biscuits and gravy, each meal a chance to practice lighting a camping stove and boiling freshly filtered water as if doing so was normal. We broke down camp at a pace that felt easy and enjoyable, working our way through the memories of an earlier lifetime twenty years before spent in the backcountry. We pulled the last of our drying underwear from tree branches before heading out on the trail up the mountain pass to High Lake a few (steep) miles away.

On our way to High Lake, we crested the ridge to peer down two sides of the Strawberry Wilderness range within view of Rabbit Ears, two spires that sit at 8,304 feet. We dropped our packs to hike the ridge of scraggly rock to the peak above the trail that dipped down toward the lake below. We snapped photos delighting in feeling on top of the world.

We rebuilt our tent village near the bank of High Lake where the face of the mountain we had just descended fell straight down to meet the water. More goats dotted the invisible ledges along the face of the mountain making them appear to be scaling air, not rock. I set my red hammock up between the trees overlooking the lake and rocked myself into a reflective state, thinking about my family who I missed.

Our second day in the wilderness was our most ambitious. We hiked five miles uphill to the ridge along which the trail to the peak splits from the trail to Strawberry Lake. We ditched our packs under the trees and hiked one mile to the top of Strawberry Mountain which sits at an elevation of 9,036 feet. After lots of jumping photos, we ate lunch back at our packs in the shade before trekking another three miles to make camp at Little Strawberry Lake, enjoying the most spectacular views of the backside of the mountain range where we had camped the night before. The ten-mile day was challenging, but so rewarding in the views it offered.

We enjoyed our last night on the trail together in a campsite that was set under the trees, a short distance from the lake. We retired to the quiet comforts of our individual tents early, drained from a full day. I read myself to sleep, feeling myself melt into my pillow and curl into my down sleeping bag.

Our last morning, we departed camp by 9:30 am, enjoying an easy descent to the trailhead past Strawberry Falls and later Strawberry Lake. Incidentally, we did not see any strawberries on this adventure, but I like to imagine this wilderness was full of their sweetness at one time. We did find huckleberries!

Upon arriving back to the cars, Cherith pulled cold cans of beer and cider from her mini fridge and my heart swelled with gratitude. I stripped out of my stale trekking clothes and into an outfit I stashed in the van. We circled and toasted Joy for planning the details of the trip, the backup plan that had gone so beautifully, and each other for bringing our best into the woods to enjoy together.

Many days later, I have begun to unpack what this backpacking adventure has gifted to me. The experience was singular and unique, no doubt, and yet, there are universal truths that have bubbled to the surface of my experience that can be applied to anyone’s life path, regardless of what is the adventure at hand.

These insights inform our human desire to live more fully expressed, more connected to our joy, and aligned with our values. Here they are . . .

1. Travel light

Carrying your belongings on your back for the entirety of your journey is a weighty proposition. Lighten your load by creating criteria for success that checks many creature comforts at the door (swap water-based foods for dehydrated for a quick win). By keeping your pack between 20-30% of your body weight, you ensure your experience hiking the trail will be as enjoyable as your time relaxing lakeside at the end of the day.

A Leadership Lens—I was cooking in my kitchen after days of dining on rehydrated food in bags, when I tuned into the new Netflix series, “Live to 100: Secrets of the Blue Zones,” a show that investigates the concentration of centenarians in areas that seem to cultivate longevity in residents well beyond the global average. A 97-year-old woman from Okinawa was asked what she attributed to her longevity and wellbeing, and she replied simply, “Don’t get angry.”

Travel light. Let things go. Be easy going.

2. Have a plan, and it back up

We were planning to circumnavigate the Three Sisters, the eponymous mountain peaks of the Three Sisters Wilderness, that is until the smoke engulfed the range and all of Bend a week before our trip. We were forced to reconsider our options. Fortunately, we wasted no time deliberating and researching new locations and routes because we already had them detailed and waiting in the wings off stage left. A new plan was proposed and we all voted with “Strawberry!” or the emoji via text and our new plan was set in motion.

A Leadership Lens—When the kids were seven and five years old, we checked in to our flight from SFO to Paris only to discover that one of us (my dear husband, Brent) didn’t have a six-month buffer before his passport expired. Suddenly, our trip to Paris and all our plans spiraled down the drain as we stood adjusting to the realization that our trip was transforming into something new. With a prescient awareness that what mattered wasn’t where we went but how we wanted to feel, I restated what I felt was most important to remember in order to guide our choice. “What’s important is that we stick together. If Dad can’t go, we choose a new place for our adventure. Wherever we go, we’ll have fun.”

We flew to our connection city of London and stayed for a week. We had no plans, but embraced the change guided by our sense of adventure and curiosity.

Plan to fly, but be ready to jump.

3. Sort needs from wants

The question of distinguishing needs from wants is a challenge to navigate when your backpacking experience is old and rusty or non-existent, as mine was. The best thing to determine which items are essential and which are fluff on a backpacking trip is to consult a trusty packing list, or two simultaneously. Beware as these lists usually include items that would serve in conditions that might not be a match for where you are headed. For example, we ditched the bear spray, but packed the odorless bags and a few had bear bags (I did not). I did include one item I wanted but certainly didn’t need—my book!

A Leadership Lens—The challenge with living in the real world (not the woods) is that what we want and what we need is separated by an increasingly fuzzy line of differentiation. Wants begin to feel like needs and soon we can’t tell what’s what anymore.

Create a practice of living with less by editing out the superfluous. You will find you appreciate what you have all the more and have a clearer connection to what is most essential to you.

4. Choose comfort

Pick the pack that sits comfortably on your body. Keep the sleeping bag you’ve had for 30 years because its warm and you love it, despite it being a bit bulky and heavy. After an energetic day, consider a kindness for your feet, your legs, your shoulders, your back, and ensure you have something sweet and nourishing to look forward to. Before we headed out on the trail, I snuck my Vuori sweats into my pack at the last minute because I was yearning to have something soft and cozy to wear in the evenings and in the mornings.

A Leadership Lens—Know yourself and what will be most soothing as you recover following a full effort. Whether you just climbed 3,000-feet of elevation or facilitated a stream of Zoom meetings, take good care of yourself by attending to your comfort and recovery.

Comfort is Queen!

5. Risk wisely for a worthy reward

There is an allure to roughing it in the woods, although, my husband would likely argue this point with me. For those who love that special combination of getting off the grid and being physically invested in the journey, a few nights sleeping on an air mattress in a tent with nothing but stars overhead sounds perfect. What feels risky is leaving behind the controlled container of our lives—our comfy beds, clean water from the faucet, and a flushing toilet. There are no guarantees in the elements, so we must simply adapt to what we find. By allowing ourselves to step vulnerability into possibility—as it concerns weather, animal encounters, unexpected delights, and well-earned pleasures—we open ourselves to expanding the range of who we are.

A Leadership Lens—Stepping into the wild is a choice to loosen our grip on the predictable outcomes that shape our lives, opening ourselves to rich insights about who we are becoming. This “wild” is a metaphor for the unknown that lies on the other side of a bold choice.

Venture forth. Risk. Learn. Adapt. Grow.

6. Take your time

If your default speed is fast and your typical output is effortful, practice letting up on the gas pedal and inviting in ease and flow. On the trail, if I was leading the group and setting the pace, I fell into a rhythm of brisk hiking, often finding that I pulled away from the group. Unconsciously, I was defaulting to my way of racing from point A to point B without setting a pace that allowed me to enjoy the journey. When I realized what I was doing, I made adjustments, and began stepping forward with more intention, noticing where and how I was placing my poles and feet on the trail. Hiking became a walking meditation.

A Leadership Lens—Savor the experience at hand by slowing down and creating space in your life to be present to what is before and around you. Ram Dass says, “Be here now.” Only in this moment—not the future or the past, but right now—are we living life. Slow down to deepen your experience of this moment.

7. Share generously

I often say that I need all the help I can get, and it’s especially true when I travel by foot, off the grid, far from civilization. If I had to do all the planning myself for a three-night backpack—have all the answers, all the resources and remedies, tools and technology—I’d never get into the wilderness. For myself, and likely many of us, the barrier to entry would feel too high with my attention to detail and tolerance for starting and completing another project too low. But thankfully, I didn’t head out into the woods alone. I had great company and lots of support.

A Leadership Lens—We each have the power to create a positive impact. Share what you can and be ready to receive what comes your way.

8. Enjoy the trip!

It’s likely anyone who is choosing to spend several days trekking up and down mountains carrying a pack full of gear and suffering the repeated setup and breakdown of camp each day is doing so out of love for the whole experience. Yep, that’s me. Maybe you are seeing a bit more of yourself in the stepmom in Parent Trap who goes camping to please her man but finds only grief and stress pressed far outside of her comfort zone, and that’s okay too.

It’s not important exactly what we choose to do with our precious days, as much as it is important how we experience them taken together. Our ability to enjoy the proverbial journey is dependent on our ability to integrate the parts and pieces of the experience into one cohesive whole that we find meaningful and fulfilling.

A Leadership Lens—Make the choices that bring you joy. By connecting with your Why, your reason for being and the values that underscore the most resonant choices you make, you can plug into your deepest source of joy and fulfillment in anything you choose to do. From this place, life takes on an effortless flow.


Thanks for reading my story about this epic adventure and what it opened up for me. I hope these insights from the trail offer you perspective as you navigate obstacles on your way to designing and living your best life—on and off the trail!


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