50M, 26.2, Women's Half

April 12th • Healdsburg, CA

I’ve Only Run This Once Before…

Casey Szesze is a New England native who’s been lucky to feel at home on a number of trail systems across the United States. From Flagstaff, Arizona to DC to San Francisco and now Bend, Oregon — most of her best friendships have been forged while sharing time on trails with other humans. A busy mom of 3, Casey works as a self-employed marketing professional in the outdoor space. Regardless of the distance, terrain and season, Casey approaches every opportunity to get outside with gratitude.

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Almost exactly two years ago, I was on these trails – running my first ultramarathon since giving birth to my daughter sixteen months prior. I was still “bouncing back” from my third pregnancy and excited to have a friend tag along for her first ever ultra – the Napa Valley 50k. “It’ll be fun,” I said. “Really, it’s just a few more miles than a marathon,” I commented encouragingly on one of our training runs. I learned a few lessons that day. Most notably to be sure to closely examine the details of the intended course as you may find out on race day that in addition to covering 30+ miles you’ll also be climbing (and descending) roughly 9,000 feet. Oops! It’s easy to overlook those things when you’re finally feeling motivated and excited about ticking off some major miles with a friend. Lesson learned.

Despite crossing the finish line nearly dead last, we did in fact, have a wonderful day. Running up through the palisades, avoiding poison oak as we made our way towards the summit of Mt. St. Helena… “Is this really a trail?” we found ourselves asking aloud in response to single track that was barely 6 inches wide. We laughed (maniacally) as we scrambled up rock faces, energy already spent with nearly two thirds of “running” remaining. My shoe split open at some point in the beginning stages of the race, but again we just laughed this off and forged on.

At roughly ten miles, the course transitions to fire roads that steadily meander their way up to the summit. In some ways this was a welcome break from the technicality of those early miles, but as the day wore on the heat and total lack of shade helped make this section just as challenging as the one before. And like the ants, we kept marching on. With every mile completed, I sang to myself in delirium “And another one down, another one down, another one bites the dust.” We pulled each other up and then back down. I found myself proclaiming to my friend with increasing regularity, “I swear not all 50ks are THIS difficult.” We giggled, sang, shared stories and eventually very silently inched our way closer to the finish line. It was a fine, albeit hard as heck, day indeed.

I’ve only run this once before. I’m sitting in my car after a quick weekend away to volunteer at Lake Sonoma 50, getting ready to run the last long run of my training block. Knowing I need to squeeze in a tough 20 miles, I think back to my experience at the Napa Valley 50k and figure this location is as good a place as any — plus, it’s on my way home to Bend. I’ll knock out 20 miles, then hop back in my car for the 8-hour drive home.

I’ve only run this once before. It was two years ago, but as I head out it’s as if I’ve known these trails for ages. I’m moving on dirt that feels more like my backyard than terrain I barely know. I can’t even remember my own children’s names at times, and here I am navigating a wilderness that seems all too familiar to me. I distinctly remember which branches of the trail to take without having to stop and regain my bearings. I recall specific tree limbs I used once before to hoist myself up and over a rock ledge or prevent me from taking a digger clear over the hillside that even in its California spring glory, softly carpeted emerald green for as long as the eye can see, would have undoubtedly resulted in injury. This feeling of being at home blows me away, and I spend almost the entire time contemplating how incredibly grateful I am to know this little slice of heaven (sadistic elements included) has been permanently ingrained in my memory.

I think about all of the places I’ve been, the trails I’ve run feeling both great and miserable, the moments I’ve recited Whitney Houston’s “I wanna dance with somebody” out loud and carefree for nature to tolerate and the times I’ve relied too heavily on running to combat an uptick in a lifelong battle with overwhelming anxiety. About 3 miles in, after a tricky descent, I’m bounding forward when I stop myself. I’m certain I’ve made a wrong turn as this no longer feels familiar to me. I’ve never stepped foot on this soil. I turn around, backtracking maybe 50 paces, and I’m back on course.

I’ve only run this once before, still I’ve carried the memory with me ever since — and I’m just now coming to this realization. Here I am, back on track with miles ahead of me, reliving a special moment in time, gathering details to sharpen the picture in my mind. I’m reinforcing just how incredible this feeling is, to work hard, smile, suffer and soar – to grunt with hands on knees and to hoot and holler at the summit. I’ve only run this once before and yet I’ve been here a million times.

About the Author

Casey Szesze is a New England native who’s been lucky to feel at home on a number of trail systems across the United States. From Flagstaff, Arizona to DC to San Francisco and now Bend, Oregon — most of her best friendships have been forged while sharing time on trails with other humans. A busy mom of 3, Casey works as a self-employed marketing professional in the outdoor space. Regardless of the distance, terrain and season, Casey approaches every opportunity to get outside with gratitude.

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Team Trail Sisters

April 12th 2025

Healdsburg, CA

50M, 26.2, Women's Half

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