42 Miles, 42 Years: A Skyline-to-the-Sea Birthday Adventure

My legs were screaming, and my watch was barking at me for being “off course”. I was leading a small pack of friends down a rocky, slippery trail in total darkness, praying my illegally parked car would still be waiting for us somewhere ahead. I’d already reached my goal of 42 birthday miles, but we were actually at 43 and change, and the finish line was nowhere in sight.

Running my age in miles has become a birthday tradition. I’ve done this for the last three years, tweaking the formula a bit each time. I’m not sure how sustainable it is – on a long enough timeline, is anything? – but somewhere in the middle of those 10 hours on the trail, it occurred to me that this is more than just a mileage goal. It’s a reflection on where I am in life, how I’ve grown, and the people I’m lucky enough to have along for the ride.

My 2025 birthday miles route was inspired by countless smaller runs in the Santa Cruz mountains, and was informed by the mistakes I made on my birthday effort last year… namely, less highway running and more beautiful trail time.

My partner (in love and crime) Jeannine woke up before the sun with me on my birthday and drove me all the way up to Skyline Blvd in Saratoga, where I hopped on the Skyline-to-the-Sea trail around 7:30am.

The weather was perfect, and I felt like a trail maintenance man, clearing out thick spider webs glistening with dew in the morning sun. It made me wonder: when was the last time someone was on this trail?

The first 6 miles were wonderful. All downhill, just cruising and loving life. Shortly after, I started my first climb on a section of trail that I haven’t seen since 2019, when I backpacked the Skyline-to-the-Sea trail (pre-CZU fire) with some friends.

Revisiting this section of my route was a trip. The landscape has changed significantly since the fire, but I still recognized portions of it. Memories flooded back of stopping along the trail to enjoy beers with friends years ago. None of those friends live nearby these days, two of are now fathers living out of state. The forest is regrowing, and so much in my own life has changed in those six years, too.

I made my way down through a stunning stretch of trail into Big Basin State Park, which is regrowing beautifully since the fires.

I approached a big exposed climb at the 16 mile mark, about 1700ft over 4 miles. I had run this section recently while scouting the route, and was not looking forward to revisiting the steep, exposed fire roads ahead, but I had a friend waiting for me up top (at the 20 mile mark) so I powered through, making space for my discomfort while holding enthusiasm for some company.

Mac was waiting for me on the trail near Empire Grade, just as planned. I had been running for 4 and a half hours at this point, and it was so wonderful to have a friend join me, especially after that last challenging climb. Checking in with him and jumping right into friendly conversation gave me a big energy boost.

It was all road running for the next 10 miles, with some familiar faces along the way.

We ran by Karrie’s house; she was waiting for us outside and joined us for a few miles with her dog.

Jeannine shuttled Caitlin up from Santa Cruz to the 26 mile mark; she’d be joining for the remainder of the route with us. We all stopped to talk and replenish supplies. As the group got bigger, it started to feel like a birthday party, and I was loving the energy.

After that, another friend (John) was waiting for us down the road. He wasn’t able to join for the run but came out on his lunch break just to say hi and wish us luck.

Once we got moving again, we ran through the Bonny Doon Ecological Preserve, and then entered the only section I hadn’t run before. I hadn’t run this section  because these were mountain bike trails, but it was the most logical connector to get us into our final park (Wilder Ranch).

As we climbed one hill after another, I asked myself, “Why the hell am I doing this for my birthday?” Then I remembered that I was surrounded by friends who took time out of their busy lives (on a Thursday!) to do this with me. A few years ago, I would have been celebrating in a bar. But life is different now. I don’t drink anymore, and my circle is smaller, but it’s also deeper. These aren’t just running partners; they’re community that’s passionate (crazy?) enough to spend a workday in the woods just to help me feel celebrated. Suddenly I felt full of gratitude and joy, and the pain subsided. For a bit.

Around 38 miles in, we met up with Steve, who was running loops in the area waiting for us. We were a bit behind schedule and he was wondering if he’d see us or not, but it all worked out, just like everything else had that day. With the full birthday party assembled, the 4 of us made our way up into Wilder Ranch for the final stretch.

The sun began to set as the ocean came into view. Every step hurt, and I was feeling pretty wiped out, but also incredibly stoked to know that we were almost done and that I’d pulled off this crazy thing – not just the physical aspects, but the logistics as well. Keeping the right pace to meet up with all of these folks at specific times without cell signal was not an easy feat!

As we made our way through Wilder Ranch and down towards the ocean for the home stretch, we got an incredible moonrise.

We ran the last few miles in the dark, which would’ve been okay if the trails weren’t so uneven and rocky. It would’ve been better if we all had flashlights, but we took our time and no one sprained an ankle.

I had parked my car along highway 1 the night before, which was a bit risky as overnight parking generally isn’t allowed. As we rounded the final corner and saw my car – still parked, no broken windows or tickets on the dash – I felt a wave of victory. We wouldn’t need to hitchhike home. And I just ran 43 miles. Hell yes.

Back at Jeannine’s house, surrounded by pizza and tired legs, I realized I couldn’t have asked for anything more. This year was a logistical challenge, full of hills and rocky trails (and devoid of cell signal) but it all worked out beautifully, like things usually do, and it wouldn’t have happened without my partner and my running community.