Point Reyes and Back: A Whirlwind on Two Wheels

When Jake Bleggi was asked to shoot engagement photos for a friend in San Francisco, he used the quick trip as an excuse to chase some longtime dreams in the hills beyond the city. Find his short story of an unplanned getaway and an ode to spinning the pedals for whatever amount of time you can here…

When a friend called me out of the blue and asked me to take pictures of him getting engaged, the first thing I did was say yes right away. The second thing was pack my bike and figure out how to make a bike trip out of it.

I set out with little to no plan. I knew I’d roll into San Francisco at 9 a.m. From there, I had to build my bike and set up my bags. By 11:30 a.m., I needed to be hiding in the park, waiting to snag some pictures of my friend’s engagement. At 12 p.m., he got down on one knee and proposed. They hugged, kissed, and cried. I snagged a few incognito photos, congratulated them, handed over an SD card with shots capturing the moment, and took off for some solo time on my bike.

Point Reyes and Back

This is where the second leg of the trip began. I had no plan and no route, only an idea of what direction I wanted to ride: north. Once I found myself on the far side of the Golden Gate Bridge, I was rolling with the punches. I had two days until I needed to be back at the airport. It wasn’t going to be the biggest, longest, or wildest bikepacking adventure. And I wasn’t going to push myself physically, emotionally, or mentally. It was more of a “Why not?” type of trip just to get out and spin the pedals. I think they’re important, too.

Despite everything going according to plan up to that point, I realized that going into my trip without doing any prior research wasn’t my brightest idea. As I stood over my bike, aimlessly staring at my phone, trying to figure out my next move, I heard a voice from behind.

  • Point Reyes and Back
  • Point Reyes and Back

“Where ya headed?” I turned around to see my soon-to-be friend, John. John was on one of the most beautiful touring bikes I’d seen in my days.  As we started discussing my plan, I found he was full of information and valuable insight. I explained my timeframe and what I was looking to get out of the trip, and he lined me out on a route that was better than anything I could have hoped to come up with on my own. After we put the finishing touches on my new plan for the next couple of days, John invited me to ride the first 10 miles with him.

  • Point Reyes and Back
  • Point Reyes and Back

We swapped bikepacking stories, and he filled my ears with welcome nuggets of life advice. We took what he referred to as the “quiet way” through town, which was back alleys and parking lots where he pointed out landmarks and told me stories from his life and his memories associated with each one. After an hour or so, we parted ways. An hour in the company of a new friend reminded me why I was out there and what I hoped to gain from the experience. It was already a great success.

I ripped up the steep hills, racing the darkness. I had an ambitious goal for my first day and had found myself distracted with side quests and pulling over to snag photos. Unlike most other trips, miles and goals were on the back burner. I set my sights on a closer campsite. I soon found myself sitting on the hillside of Pantoll Road, watching the sunset over an endless ocean. The sounds of yipping coyotes filled the air on night one, a reminder that I’d escaped my daily routine. I managed to snag a picture of one that thought it would be fun to talk all night while I was trying to catch some sleep.

  • Point Reyes and Back
  • Point Reyes and Back

The next morning, I rallied to the coast. I had one clear mission on the coast, and that was to find oysters. I had never had an oyster before the trip, and my hero Anthony Bourdain once said, “I blame my first oyster for everything I did after: my decision to become a chef, my thrill-seeking, all my hideous screw-ups in pursuit of pleasure.” I had to find out for myself if this was true. Point Reyes Station was the lunch destination and the furthest point from the big city I would make it to.

Strolling up Highway 1, I listened to Slaughterhouse-Five and enjoyed every second of it. “So it goes.” I had never been on a solo cycling trip before, and I learned that this was the place to do it. Although I was out there alone, I didn’t spend much time by myself. My day on Highway 1 was filled with quick conversation and friendly fellow cyclists letting me snag a quick draft. The vibrant old city of Point Reyes Station was my perfect halfway point on my trip—a quaint town filled with small shops and local restaurants. What more could a person ask for when looking to resupply and hang out for a few hours?

Point Reyes and Back
  • Point Reyes and Back
  • Point Reyes and Back

I found a charming farm-to-table restaurant. It was the place where I would find my oysters and kick off my pursuit of pleasure. I ordered a full chicken and three oysters. I nervously waited for them to arrive. About five minutes after I sat down, they showed up. They were on a leaf of lettuce and covered with a tangy sauce. I ate the first one, and while it was delicious, it felt like a lot of fuss for what it was. It didn’t give me the experience I’d spent the last day and a half riding in search of, but at least it was a hell of a ride. I left the restaurant full but underwhelmed. 

It was time to start heading south. I was only on the road for 30 minutes when I saw a flashing sign on a bar: “Oysters.” I knew this was it; the half-shell sea creatures I’d been looking for had to be waiting just inside. I ordered a beer and a half dozen oysters. They came out on a tray of ice. This was it. Every episode of Parts Unknown I had watched had led up to this moment. I squeezed a little lemon on top, lifted the shell to my lips, and threw my head back.

Point Reyes and Back

This is the part where you might expect me to tell you the fireworks went off in my head or that everything that I didn’t quite understand all made sense now. In reality, it was the end of my rambling inner monologue and the moment I accepted that Tony and I didn’t quite have the same awakening experience. With this side quest accomplished and a chapter closed almost as soon as it was opened, it was off to the hills.

Point Reyes and Back

Climbing away from the ocean and into the vast green rolling hills, cruising dirt roads past cow pastures was a welcome change. These rough, slow miles gave me an opportunity to peel back the layers and savor the little things. Watching more of my ole coyote friends run off in the hills in the distance and cows graze on an open skyline with redwood forests in the background was therapeutic. I would have stayed in those hills for days if I could have, but the miles were slow going, so after a few hours, I weaved my way back to the highway and caught some fast miles on the blacktop. After a few hours and a quick stop for food, I found myself a quiet little campsite on the edge of an outcropping overlooking the ocean on three sides. Watching the sunset and the waves crash, I slowly drifted to sleep on the last night of my whirlwind tour. 

Point Reyes and Back
  • Point Reyes and Back
  • Point Reyes and Back

The next morning, I woke to fog and a brisk breeze. I had seen what I had come to see and experienced more than I could have hoped for, especially in such a condensed amount of time away. I had a flight back home in eight hours, and it was time to make it back. Punchy climbs and ripping down hills filled the morning before I knew it.

  • Point Reyes and Back
  • Point Reyes and Back

I was back in the town I had ridden through with John just a few days earlier. Although I had places to be, I still found time to take “the quiet way” one more time. As I arrived back on the other side of the iconic red bridge, the adventure was nearly over. The people, the food, and the beauty of Northern California by bike will leave a lasting impression on me. My little tour is an experience I’ll always cherish, and even if my foray into oysters was a bust, the trip was a powerful reminder that the hours pass differently on the bike, and no amount of time away on two wheels is too short. Now I just need another excuse to pack the bike and head somewhere new again.

Jake Bleggi

About Jake Bleggi

Jake Bleggi is from a small farm town south of Salt Lake City Utah. From the time he was young, you could find him on a bike riding in the mountains above his home. He picked up my first camera when he was 12, and since then, he’s been trying to capture experiences as authentically as he can. Find him on Instagram @jake_bleggi.

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