Hello! This is Yoshimoto from Circles Tokyo!
Time flies—it has already been two full years since Circles Tokyo put down roots here in Tokyo.
To celebrate this two-year milestone, we chose not to throw a flashy party or hold a sale. Instead, we decided that "everyone getting out on their bikes and heading beyond the routine" was the most "Circles" way to celebrate.
Despite a tight schedule with a 9:30 PM Friday meeting time, an incredible 11 people joined this venture! It turned out to be the ultimate ride, so I’d like to share how it went to serve as inspiration for your own future rides.
Escaping the Friday night hustle. Bound for Tokyo Bay at night.
After closing the shop at 8:00 PM, we pedaled away, stealing glances at the bustling streets of Shimbashi on a lively Friday night. There was a vivid contrast between the unique energy of the city on a Friday night and the wilderness we were headed toward. The destination for this anniversary ride was Izu Oshima, an island located 120km south of Tokyo.
At 10:00 PM, the large ferry pulled slowly away from Takeshiba Pier. After boarding, we initially scattered to our respective areas, but soon, without anyone needing to say a word, people naturally gathered on the deck. We toasted with the spectacular view of the Rainbow Bridge—an infrastructure marvel you never get to see from the ocean side in daily life—and the night view of Tokyo Bay as our backdrop!
Participants who were total strangers until moments ago hit it off instantly through the powerful common language of "bicycles," becoming friends. That’s truly the magic of a ride event where bikes connect people.
The ship passed Odaiba and headed south, quietly cutting through Tokyo Bay. Whether they were turning in early to prepare for the next day's ride or continuing to enjoy drinks while feeling the sea breeze, everyone spent their time on board differently. I slipped into my bunk just past 1:00 AM. What surprised me was that even at that hour, we hadn't yet cleared the Uraga Channel. There was so little movement that I forgot I was on a ship, and I fell into a deep sleep in the silence of gliding across the calm surface.
The next morning, at 5:30 AM, 30 minutes before arriving at Oshima, we were woken by the ship's announcement. After getting ready and heading to the deck, we felt as if we had arrived in another world.
Breathing in the sea air, we all unpacked our bikes under the brightening sky. As we tightened our thru-axles and checked our derailleurs, the excitement for the ride ahead reached a fever pitch.
Front-loading the peaks. The full picture of the Oshima loop ride
The course profile for this ride was an approximately 55km loop around Izu Oshima, starting from Okada Port and heading clockwise. Looking at the distance, it might seem moderate, but the total elevation gain hits 1,000m. The route is designed to fully cover the island's dynamic terrain and photo spots, including the primary goal: the "Ura-Sabaku" (Back Desert).
As soon as we departed Okada Port, the climbing began in earnest. As is obvious from the route cross-section, the "first half is the biggest challenge." The trick here is to knock out the elevation gain all at once. By doing so, you reach the lunch spot at Motomachi Port at the perfect time when your hunger is at its peak!
The middle section takes you through the Ura-Sabaku before heading to "Sushiko" at Motomachi Port, where we had lunch reservations. The routing isn't just about riding; it includes stops at the nostalgic sights of Habu Port and the "Great Stratum Cross-Section," which lets you feel the pulse of the Earth, capturing the grand scale unique to Oshima.
Then, for the second half, you traverse the "Sunset Palm Line" that traces the coastline from Motomachi Port, eventually returning to the starting point at Okada Port. It’s a perfect day-trip plan where the story of the day comes to a beautiful conclusion.
Departure. Spinning pedals, decoding the context of the land
The ride officially began. For the first half's main climb, everyone pedaled at their own pace. As our heart rates spiked and we were gasping for air, we stopped for a photo at "Sentzu no Kiritooshi," a place that feels like stepping into a Ghibli movie. Feeling somewhat refreshed by the mystical atmosphere, we pushed further toward the summit.
My style for coping with the relentless intensity of a long climb is to distract myself by carefully observing the surrounding scenery and terrain. While looking at the vegetation—the same way one might read road conditions—I suddenly noticed, "Oshima has an awful lot of camellia trees."
I looked it up later, and it all made sense. Volcanic ash soil and relentlessly strong, salty winds. The islanders have historically planted camellias as "windbreaks" to protect their houses and fields from such harsh natural environments. At one time, camellia oil harvested from them thrived as the island's main industry; while it declined for a period, I learned that local people are currently working toward its revival. What had just looked like scenery instantly took on the contours of the islanders' lives.
Unfortunately, the flowers had mostly fallen by the time we visited, but if you go when they are in full bloom, you can ride through vivid tunnels of red and pink. Being able to directly feel and imagine the history and livelihoods of the land through your own skin while spinning the pedals—this is the greatest charm of the bicycle, the vehicle we are so drawn to, right?
The extraordinary nature of Ura-Sabaku and the true value of the ATB
After finishing the long, arduous climb, we finally arrived at the entrance leading to the Ura-Sabaku. From there, it’s about 1km of gravel road suitable for bikes leading into the desert. As we advanced, a fence appeared restricting vehicle access; we stashed our bikes and walked a short distance, and the view suddenly opened up, with an overwhelming panorama jumping into sight.
Covered entirely in scoria from the eruption of Mt. Mihara, the scale of the scene makes you doubt whether you’re still in Japan. The small stones that make up this pitch-black earth look heavy and dense, but when you pick them up, they are surprisingly light, filled with air pockets.
When you dive into such an extraordinary location, you find yourself getting seriously excited, even as an adult. The pure novelty of riding a bike over crunchy volcanic gravel was so thrilling that someone even lost their balance and took a spill (lol). But that’s what makes for the best fun, right?
You might think, "Do I need thick off-road tires to ride there?" Rest assured, you don't. While there are loose sections where your tires might sink in a bit, the ground is basically firm. As long as you are conscious of your center of gravity and can pedal while effectively weighting the rear wheel, a road bike can move forward perfectly well.
In fact, some of our participants even conquered this section on track bikes or small-wheeled road bikes like a BIKE FRIDAY / Pocket Rocket! Whatever the equipment, as long as you have the rider's skill and pure curiosity to "want to ride," the path will open up. It was a moment where we enjoyed our bikes freely, without being bound by equipment specs.
Superb downhill surrender to gravity, and a multi-millennial time scale
Once you leave the rugged black world of Ura-Sabaku, a superb downhill awaits, making it feel as if you are diving into the deep blue sea. Actually, I’d been feeling it ever since we started: the road paving on Oshima is incredibly well-maintained. Transferring the tire grip firmly to the asphalt and clearing corners while surrendering to gravity without a hint of anxiety is the reward that only those who endured the painful climb get to enjoy. The views of "Fudeshima" and Habu Port seen from the heights after the descent painted a beautiful, cinematic contrast.
Before I knew it, it had been four hours since we left Okada Port at 6:30 AM. It was time for the final push toward "Sushiko" in Motomachi Port for our 11:30 AM reservation. However, the coastal road’s fine ups and downs and the lack of resupply points began to steadily drain our legs. Once the "Great Stratum Cross-Section," looking like a giant Baumkuchen, came into view, the finish line was right before our eyes.
Facing this magnificent stratum, where layers of volcanic eruption history from tens of thousands of years ago are stacked, made me realize that the time we spend spinning our pedals is, in the grand history of the Earth, just a split-second blink. Feeling that sense of romance, we tackled the final climb.
Lunch soaked in the island's bounty, and a trip home gliding over the sea
At Sushiko, we had the "Island Bowl," filled with Oshima’s specialty "Betto" (white fish marinated in chili soy sauce) and plenty of fresh local catch. The bounty of the island soaked into every corner of our parched bodies, which hadn't had much in the way of supplies. It's no exaggeration to say that I’d been riding just to taste the deliciousness of that single bite.
There were about 10km left from Motomachi Port to Okada Port. We cruised the beautifully maintained coastal "Sunset Palm Line" at a comfortable speed, enjoying the scenery while cradling our full stomachs.
The trip back was a 1.5-hour boat ride from Okada Port on a jet ferry. Because of its structure, which uses gas turbine engines to spray seawater and lift the hull itself above the surface, it’s minimally affected by waves, keeping vibration to a minimum. The feeling of traveling at an unprecedented speed, as if flying just above the sea surface, was a little attraction fitting for the end of the trip.
The pedals won’t stop in the third year
Turning around from the torrential rain forecast just a week prior, this 2nd-anniversary Oshima loop ride was blessed with spectacular clear weather. The dynamic changes in scenery brought on by the loop route and the real, tactile sense of overcoming sections with zero supplies by encouraging each other—these are all invaluable experiences gained precisely because we turned the pedals with our own legs.
There is a reason why we at Circles Tokyo don't just maintain and sell bicycles, but continue to venture out of the shop to plan ride events. It is because we want to directly share with you the moments where that ultimate analog machine, the bicycle, fulfills its function of connecting people, or people with the culture of the land.
Two full years since we put down roots in this city of Tokyo. As Circles Tokyo enters its third year, we are determined to continue sharing its profound charms.
From consultations on gear to strategy meetings for how to play next weekend. It would be amazing if we could keep spinning pedals and laughing with you all in our third year at Circles Tokyo. Thank you for your continued support!
