Five Bikepacking Overnighters to Celebrate 30

I have never thrown myself a birthday party. Not once. I confess this to my friend, hoping he’ll cut me some slack. Instead, he doubles down. “Your 30th birthday is a big deal! I’d even want my close friends to fly in for mine.” His confidence is equal parts intimidating and motivating. I think of my friends who have moved in recent years—to Seattle to start a family, to Chicago for medical school, to New York City for a change of pace. I miss them, but having them fly to me feels like a big ask.

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What if I go to them instead? This is equally new territory for me. Growing up, we took family trips to see Yosemite, not Uncle George. It wasn’t easy for my immigrant parents to fly abroad, so there was no such thing as an annual family reunion. The thought of visiting friends—people, not places—never crossed my mind. It’s funny how family habits set patterns for what we consider normal. Now, as I turn 30, I find myself contemplating a series of trips to the people who matter. What better way to ring in a new decade? I brainstorm five weekends in Washington, Wisconsin, Alaska, California, and New York. A short text message to each friend sets plans in motion:

“I’m turning 30 this year, and I think it would be meaningful to celebrate by flying to different states and sharing something I love. Would you be down for an overnight bikepacking trip later this year?”

Olympic National Park, Washington

Jamie and I step under a wooden archway that spells out “Olympic Discovery Trail Adventure Route,” and it feels like we’ve crossed into another world, even though the parking lot is just 50 feet back. Singletrack leads us through a thick carpet of moss and fern under a canopy of cedar and Douglas fir. Jamie tells me that we’re riding through one of the only temperate rainforests in the world, right here in Washington’s Olympic National Park. Knowing this, the overnighter feels even more like magic.

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We pitch camp by the shore of Lake Crescent and crack open cans of bourbon cream to toast to my inaugural birthday bikepacking weekend. A perk of the overnighter is having extra room in our bike bags to pack an extravagant dinner: Japanese egg drop soup, chili oil noodles, and a three-foot-long churro for dessert. As dusk paints the lake in strokes of deepening shades of blue, Jamie and I trade stories of bike role models like “North Shore” Betty, who still shreds trails into her 70s, and “America’s Bike Mayor,” John Bauters, whose advocacy has shaped Emeryville, California, into one of the most bike-friendly cities in the country. We ponder a lifestyle that is more connected to the outdoors, and how we can positively influence others in our own way. 

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The one thing missing from this overnighter was our friend, Lynne. The three of us bonded during triathlon training in San Francisco and a bike trip in Taiwan. Lynne couldn’t join us this time, sharing that she was pregnant with her second child. After the Olympics, Jamie and I spent time with her family in Seattle, and in the spirit of the trip, we gave her toddler a Woom bike. Give it a few years, and perhaps Lynne and her growing squad will join us on the next trip.

Kettle Moraine State Park, Wisconsin

Kisses from Cindy’s dog nudge me awake in the heart of Chicago. We hit snooze, even though it delays the start of our bikepacking weekend. This is Cindy’s first golden weekend after 20 consecutive days of waking up at 5 a.m. for her OB/GYN residency. In her world, a “golden weekend” means she gets both Saturday and Sunday off. Unbelievable that something most of us take for granted merits a special name for those who rarely get it.

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We drive across state borders into Wisconsin, arriving at Kettle Moraine State Park late in the afternoon. I had imagined this weekend as Cindy’s escape from the city, and when I’d done my research, the red pine forests of Kettle Moraine caught my eye as an ideal nature retreat. Once we hit the trails, though, the regret hits, too. The rooted singletrack is tough for Cindy’s first time on a mountain bike, and it’s soon a losing a race against daylight. I can’t help but think of the I&M Canal, the backup option closer to Chicago that I’d brushed off as “too urban.” I got so caught up in my vision of this weekend that I overlooked the obvious.

As the last light vanishes from the treetops, I realize it’s time to scrap the original plan. Rather than pushing on for a full bikepacking experience, we double back in the dark and set up camp near the start. We’d do an easier day ride tomorrow. There’s no sense in brute-forcing the “bikepacking” part for the sake of the script.

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Cindy and I trace our friendship back to elementary school, and reuniting with her brings a wave of nostalgia. I was always the “artist,” and she was the “writer.” As time passed, these broad strokes of childhood sharpened into the more defined details of our adult lives. Cindy moved to Chicago eight years ago for medical school and residency, her 20s marked by the relentless rhythm of early mornings and late nights. Meanwhile, my path led to a software engineering job and a balanced routine, leaving me with the energy to chase “type 2 fun” on weekends and go deep into my outdoor passions. Cindy tells me earnestly that her 30s will be the decade she finally defines her hobbies. Introducing her to my world of cycling is exciting, but I am most of all thrilled for Cindy to discover her own passions in the years to come.

Denali National Park, Alaska

Six big letters DETOUR are scribbled in Sharpie on the ranger station map. There is a single gravel road that leads into Denali National Park, and for years, it has been cut off at mile 43 by a landslide. With much of the road sealed off, everything beyond mile 43 has returned to the pristine wilderness it once was before the road’s construction in 1915. For the determined cyclist, there’s still a way through. The ranger points out the four-mile detour that follows a riverbed to bypass the closure, but then comes a string of warnings no cyclist wants to hear: “big rocks,” “pretty gnarly,” and “you’ll get wet.” I glance over at Dani and make a wincing face. 

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The detour is a trial by fire: hike-a-bike through mud, rocks, streams, and a final assault by mosquitoes. Alaska doesn’t hold back. Dani proclaims loudly her desire to hurl her bike into a dumpster. It’s a feeling any bikepacker can relate to. But for every ounce of bad, Alaska makes up for it with equal parts beauty. After what feels like an eternity, we reach the spot where our GPX waypoint promises we’ll reconnect with the road. The final hurdle is carrying our bikes up a 200-foot bushwhack to reach it. My watch reads 11 p.m. when we finally arrive at camp under a pink dusk sky, having wrung every last drop of daylight from Alaska’s long summer days. We’ve made it past the detour in one piece.

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“I look forward to the day we can look back and see the detours we took in life,” Dani once told me out of the blue. Looking back at our Denali detour, it feels a little too on-the-nose to wonder now if Dani will see our friendship as a kind of detour. Earlier this year, I ended my friendship with Dani, who, for a moment in time, had been my closest friend. I could dress up this moment with all kinds of cliches—There are no real detours in life; everything happens for a reason—but none of them fit, and all of them are cheesy, so I’ll leave it be. There is a deeper lesson in here, somewhere, but it’s a knot I’m in no hurry to unravel. Physical detours are easy to map out; the metaphorical ones may not be.

Marin Headlands, California

Together, we are a parade of DIY brilliance. Bungee cords, Voile straps, bike racks, and trailers transform a pile of gear into eight makeshift bikepacking setups. Chandler’s rig stands out, defying gravity with a 65-liter backpacking pack perched atop his rear rack. After several trips out of state, it feels right to bring the adventure home to San Francisco. Many of my friends are not cyclists, but their enthusiasm—or maybe their dedication to celebrating my 30th—makes up for their lack of experience. No fancy gear necessary. 

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We pedal across the Golden Gate Bridge, and the headlands unfurl in a blur of gold as we move through them. The rhythm of the landscape rolling by, syncing with our body’s movements, is more than just a feeling—it’s known as “optic flow.” This term describes how objects in a scene shift as you move through them, for example, a tree growing larger as you pedal toward it. This visual-somatic experience activates your body’s parasympathetic “rest and digest” mode, calming your brain’s stress response. It’s no wonder so many of us refer to our sport as “bike church.”

Getting to Hawk Camp in the Marin Headlands isn’t all “rest and digest,” though. The steep, rocky trail to camp has all eight of us hiking our bikes, our lungs burning as we pull in salty air from the bay. Fog slowly creeps in and clings to the trees, turning into droplets that fall like rain as we brush by. We huddle close for warmth and share stories in the dark until we are forced to retreat into our tents when our jackets soak through. An old quote rings true in this moment: “The coldest winter I ever spent was a summer in San Francisco.” Still, for all its stubbornness, the fog carries a certain comfort as a symbol of home.

Shawangunk Mountains, New York

Jessica and I stand atop the dramatic cliffs of the Gunks and peer down at the quilt of red and orange below. We find ourselves here after climbing up gentle carriage roads, perfect for Jessica’s first time riding gravel and forgiving of our borrowed road bikes (after a few overnighters, I’ve finally learned a thing or two about picking easier terrain). We ponder the future, reminisce about our years as coworkers, and then drift into those effortless silences that happen when you’re comfortable with someone.

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It was Jessica who first showed me the power of side-by-side conversation. Most people suggest, “Let’s grab coffee before work.” She’d ask, “Let’s drive to Half Moon Bay for sunrise?” We’d set off in the dark, wind down the Pacific Coast Highway, and arrive back in time for our first meetings. One person behind the wheel, the other riding shotgun—it opens up a more honest dialogue. Social insecurities, relationship woes, career angst. Sure, eye contact has its importance and avoiding it entirely is a social crutch, but there’s something freeing about staring at the road ahead and letting your guard down. As Jessica and I pedal through the fall colors of the Gunks, I think fondly of our drives to Half Moon Bay. Back then, our conversations flowed just like they do now, meandering through every topic imaginable. Watching the world unfold around us side by side invites a rare and precious candidness.

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Each of my five birthday bikepacking overnighters brings a sense of closeness that inspires me to keep the tradition alive for future birthdays. Whether bikepacking, hiking, gathered around a campfire, or sharing whispered conversations with a tentmate before sleep wins over, it’s these shared focal points—the road, the view, the fire, the stars—that allow for a kind of openness that sitting across a table never could. As cyclists we know this intuitively: some forms of connection need no direct gaze, only a shared horizon.

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