Somewhere west of Greenfield I decided to become a trespasser. If anyone had a problem with it, I figured they could take it up with Junipero Serra.

Serra had inspired me to end up here – some 35 miles north of Mission San Antonio, more than an hour by car from Salinas, biking into a wind that had me cursing God. I surveyed the 100-yard, wind-sheltered shortcut through the farmland below me and felt the Father’s backing. After all, Junipero made his own roads.

As I descended into the field of broccoli, trudging down a muddy track, the workers in the field pulled up from the soil and showered me with smiles. Pedaling forward through the puddles, I smiled back, and for a moment we shared fleeting grace, a short deliverance from earthly toil.

Out of the field and back onto a road – having just saved an added mile in the devilish headwind – I wondered what the farmworkers must have thought of me and my oversized backpack and bamboo bike, rolling uninvited through the broccoli.

Father Junipero Serra fashioned his diet after the Virgin Mary’s – small portions of fruit, vegetables and fish – and swore off terrestrial meat unless it was a matter of survival. He was known to recite hymnals in his sleep, in his excellent singing voice.

These are the sorts of things I learned before my trip, while piecing together his biographies and histories, but my most burning questions remained unanswered: Did native Californians suffer more, or less, because of his legacy? Is his medieval piety relevant in our busied Age of Information? Should we consider him a saint, a slavedriver or a complete nut who whipped, burnt and beat himself needlessly?

I wondered if those questions would start to affect my diet and song-free sleep, if I would perhaps take a shine to self-torture – and I hoped to answer them on the road ahead.

It was on a road that the journey began, but it wasn’t the 101 alley that Serra traveled most. As I hurtled south toward Monterey on a scenic stretch of the 280 (between highways 1 and 17), I noticed for the first time that it was called the Junipero Serra Freeway – an odd dedication for a man who preferred to walk.

It occurred to me how little I remembered about Serra since my fourth grade education. One fact was all I could muster: The missions were built to be a day’s journey apart. From that, a crusade crystallized. I would retrace Serra’s path through the three missions of Monterey County in as many days, and discover, through some sort of shared experience, what lay at the core of a man who is known by so many, but who is still not understood with any depth outside of tight academic circles.

Research revealed that the missions were separated by a day’s ride, not a day’s walk. With limited access to a horse or a mule, I set my sights on a bike, and a chance meeting led to Stalk Bicycles, a small shop in Oakland that builds custom bamboo bikes to order.

The sleek bike frame was to consist entirely of bamboo (which has the tensile strength of steel), with joints bound in hemp fibers. The hemp and bamboo evoked the humble durability that Serra personified – he repeatedly walked hundreds of miles on a bum leg, and he did it in rough fiber sandals fashioned after the footwear of Jesus.

In the two weeks the bike was being built, I dug into Junipero’s story like he did into his own flesh, and was amazed by the devotion he brought to his ambition.

Bilocation – the ability to be two places simultaneously – was a word I had to look up, but for the southwestern missionaries in Serra’s time, it was another part of God’s mysterious plan.

By the late 1600s, every New World missionary had probably learned of Sister Maria de Agreda, a mystical Spanish nun who, in the words of Serra scholar Maynard Geiger, had “been supernaturally transported to New Mexico to announce Christianity to the natives” at least 500 times, starting in 1620. While cloistered in a convent in Agreda, Spain, every aspect of her being was said to appear an ocean away, as often as four times a day. Once transported, de Agreda’s ability to communicate with the natives was made possible by her gift of tongues. She told them to find the Franciscans, and with them, baptism.

“She attributed her language facility to divine grace,” writes historian James A. Sandos, whose Converting California: Indians and Franciscans in the Missions provides the most objective view of Serra and the Franciscans to date.

Church investigations pointed to the extraordinary: The Jumano natives of New Mexico, a people no missionary had ever visited, confirmed a woman preached among them – always wearing a blue-hued overcoat.

Serra often travelled with de Agreda’s book Mistica Ciudad de Dios. According to Serra’s best friend and biographer Francisco Palou, her powers gave him no small comfort that his aims – to convert pagans and “harvest” their souls – were similarly blessed by the will of God.

I hoped for a similar blessing, but I knew bilocation from South County to Carmel was a stretch. I was going to have to grind it out.

When Serra and his pack train first came to the San Antonio Valley, as history tells it, a single native watched from the trees. My own arrival attracted even less attention. As my friend drove to the head of the remote, oak-studded valley (known to Serra as the “Valley of the Oaks”) to drop me and my bike off, the stately Mission San Antonio de Padua came into sight. With its beautifully reconstructed campanario (bell tower) and archways, it immediately announced itself as a place of consequence.

“This was a prosperous mission,” says Franki Grau, the mission’s gift shop manager. “But it was devastated by secularization.”

While successful by mission standards (in 1828, it boasted 10,000 cattle and 8,000 sheep), it still wasn’t making anyone rich.

“[California] never really produced the way Spain wanted it to produce,” Sandos says. “It’s not sending revenue to the coffers of Mexico City like the other colonies are.”

For Serra, constantly holding his hand out to the fading fortunes of the Spanish empire, funding the missions was a similar struggle, and it was a pursuit in which he was tireless.

“There were not lacking persons in authority and of rank,” Palou maintains, “who said concerning him: ‘This Father Junipero is a holy man, but in this matter of asking for help in the founding of missions he is a very burdensome saint.’”

Franciscans from all over the world are known to visit the San Antonio Mission for a novena (nine day devotional retreat), but when Grau bid farewell on our trip, there were no other guests in the spartan hostel-style adobe rooms. For $60 each, we had the historical landmark to ourselves.

The nearly 1-acre garden courtyard – with its rose bushes, adobe fountain and painstakingly manicured lawn – felt like a Catholicism-meets-Zen playground. As the evening turned dark, the lights along the adjacent outdoor hallways illuminated murals and the structure itself.

The chapel was left open, hymns playing. I took to my knees in the confession booth. I asked for forgiveness – and for Serra-style strength.

“Always go forward,” went Serra’s motto. “Never turn back.”

Before my wheels hit the road, I was poised to violate this simple tenet: As I removed my bamboo bike from the car, I found that the cable-stops for the gear and rear-brake cables had come unstuck from the frame, and a quick ride-around proved that I had no functioning gears and no rear brake. (This flaw has since been repaired free of charge – the job had been rushed for the trip.)

Some quick thinking led to a roll of rescued masking tape found on the grounds, and zipties offered by a friendly caretaker who lives next to the mission.

Serra once used a similar makeshift band-aid to avoid turning back: On his journey from Baja to San Diego, his leg, which had been bitten by a snake or mosquito shortly after he arrived from Spain, began ulcerating badly. The expedition came to a halt. Not willing to remain behind, Serra asked a muleteer to make him a poultice, like he would for an injured mule. The wound improved, and Serra was able to go forward.

Besides, Serra had a decidedly different openness than I did to a nasty or accidental end – should he die on this godly road, whether from bad brakes or an infected bike, so be it. “He wanted to be a martyr,” Sandos says.

Not me. When I rolled off the property, there was a gift shop-purchased gift-store trinket of St. Christopher – the patron of travel and travelers – stashed safely in my pocket.

The ride out of the valley was smooth and serene. The bike held up, and it seemed my only concern might be the growing heat.

Fortunately on the climb up the substantial grade on Jolon Road, a commercial pickup pulled up beside me, and the driver asked if I wanted water. Tom from Miller’s Pump & Drill Co. filled my canteen to the top from a cooler in his truck.

“Nice valley,” I offered. He took a moment, then said, “Yeah. But it’s not worth anything.”

The winemakers of Paso Robles, who are ever pushing their vineyards farther north, would disagree, and Serra – who saw in this valley a great potential for converts – would have too.

The long, speedy descent down Jolon Road towards the Salinas Valley was a harrowing, one-brake feat that stretched St. Christopher’s powers. As I slowed onto level ground, slicing through pastureland, I saw crosses flying by. A second later, I realized they were telephone poles.

I reached the U.S. 101 – completing a 25-mile stretch – in just over two hours, and with only 20 miles left to the next mission in Soledad, and my soul still full of energy, I felt Serra at my back.

All too soon though, I would feel a similar force of nature in my face.

I’m not sure how Serra would have felt about the use of an iPhone for navigation, but Google became an essential tool to map my progress, and kept me off the 101 as much as possible. But when Jolon Road came to an end, there was no way around the highway. I gritted my teeth.

Three miles of biking on the 101 passed with surprising ease, but once I exited into the farmland west of the highway, the punishing elements made one thing clear: For the sins I’d confessed the night before, there would be penance.

Blistering headwinds pounded me. On my custom bamboo rig – which I had designed to be an upright get-up with cruiser handlebars – I felt like a target. Miles of farm trucks kicked dirt up in my face. Wind desiccated my lungs. The landscape became a slog of monotonous, mind-numbing leafy greens. Eventually the pain set in deep: My legs became throbbing slabs of rubber, and my shoulder straps, straining under the heft of my pack, sent daggers down my neck. I could only imagine the suffering if I was on a less shock-absorbent bike.

My spirit sought out the horizon for a wayward angel – or taxi. Though I would have loomed 10 inches above the 5-foot tall father, I was well short of Serra in terms of toughness. Pain was his pastime. He actually sought it out to better experience what Jesus Christ dealt with, hence the self-mutilation.

“Serra [was] one of a small group of ascetics within the Order known as ‘fervents,’” Sandos writes. “To increase the pain and further mortify the flesh, [he] embedded pieces of metal into the cords of the discipline [or whip] as well as into the hair shirt he wore.” He also held candles to his skin in front of crowds. When he beat himself before groups in Mexico City, devout followers offered to take his place, if only to stop the spectacle.

To ease my own pain, I took to walking for spells, Serra style, and feet felt faster than on wheels. A quick calculation showed that I was now traveling north at about 5 miles an hour – at least four times slower than the wind flying into at me – dashing any hopes of reaching the Soledad Mission by closing.

When I reached my humble motel that evening, the wind had depleted me entirely. I took a two-hour nap before I could summon the strength to eat. In the mirror, I saw enough salt – sweat, crystallized by the wind – to put in a grinder.

My deep, dreamless, hymn-less sleep that night would have been considered an indulgence by Serra.

“He would pass nearly the whole night in watching and prayer,” Palou writes, “so that the sentinels, when they changed watch… used to say, ‘We don’t know when the [Father] sleeps.’”

When he did, the Father would often “cry out in his sleep, using these words: ‘Gloria Patri, et Filio, et Spiritui Sancto.’”

After a breakfast in which, like Serra, I shunned meat, I came to Mission Nuestra Señora de la Soledad at its 10am opening, and was the only one there when I first arrived. It seemed fitting for a place known as the “Lonely Mission.”

Above all else, Soledad captivates with humility. The structures that once housed the mission’s industries lay in authentic ruin, and its small chapel syncs with Serra’s asceticism. Everything about the place – from its single-story design to the wind-blocking trees lining its northern and western flanks – seems just as it should be, and in its howling, obscure desolation I pictured the plight of the natives who agreed to be baptized and became unwitting subjects of Spain.

“Serra wanted to believe… the [natives] were hungry for baptism,” Sandos says, “and whatever temporal suffering they might have to endure was a minor thing compared to the salvation of their souls.”

Had I been stuck in this valley as they were, and forced to perform upwards of six hours of daily labor that might include digging, planting, brick-making, weaving and the ceaseless grinding of flour by hand – as well as commit around four hours a day to prayer and ritual – I would have been tempted to lay down my tools and run for the hills. Any natives who made that choice, however, were relentlessly hunted down by soldiers and brought back to the mission to be whipped. Those who shirked labor or religious duty were also flogged.

The short path to baptism under Serra involved a few weeks of memorizing prayers. But Sandos says natives didn’t often comprehend the deal they were making: “Serra deluded himself seriously. He believed that once a native was baptized, that native was a convert.”

When imagining what their mindset might have been, Sandos channels Hank Williams: “If this is the Promised Land, then I’ve had all I can stand… I just don’t fit in, but I can’t go back home again. I’m stuck here with my village on my mind.”

A life confined to this wind-swept valley was a rough prospect to consider, and as I made my way onto River Road after taking my leave, my thoughts tilted toward life’s temporal pleasures, and the salvation of my mood. The wind, my nemesis, also makes for excellent grapes, and I figured I was due some fruits for my suffering. Serra mostly abstained from alcohol, but I had learned by this point that I was far from a Franciscan or someone who saw virtue in pain. For oenophiles, nearby River Road is a new mission trail, a lush landscape dotted by award-winning wineries such as Paraiso, Hahn and Talbott.

As I emerged from the last tasting room, the clockwork gales started ripping, but for the first time in 24 hours, I wasn’t worried. I couldn’t say whether it was the cultivated splendor of River Road or St. Christopher in my pocket, but it felt like more than just grape juice. When I finally hit the Monterey-Salinas Highway and encountered the wind’s coastal cousin, my legs found new life.

The lift must have been similar to what Serra felt coming home from his many travels. Soon, I would be resting in the company of friends, and the Pacific would open before me.

Carmel’s Mission San Carlos de Borromeo was the last place Serra called home, but the cell he slept in was the only part that existed in Serra’s time. The rest built was up around it.

When I rode there the next day, I had a riding partner leading the way on a “scenic route” from Seaside, guiding me over a maddening number of Jacks Peak hills that cover the highest point on the Monterey Peninsula. I cursed him silently, vocally and metaphysically, even as I thanked the heavens for such a light and nimble bike.

An ornate wedding was in preparation as we arrived at San Carlos, and the buzz of activity offered striking contrast to lonely Soledad and isolated San Antonio. At the left of the chapel’s altar, a stone carved with Serra’s name marks his final resting place, and I stood contemplating his final days. While he knew he had made his mark on the world, sadly, most of the natives he helped convert fell victim to Spanish diseases, most notably syphilis. When the Spanish first arrived in California circa 1770, there were 65,000 natives living in the mission zone. By 1830, there were only 17,000.

Hence activists in the ’60 and ’70s began to accuse Serra and his missions of genocide. Some historians, though, take issue with this claim.

“If there’s anything that the Spanish and the Franciscans wanted,” Sandos says, “it was not dead natives. They wanted Christian, Spanish-speaking peasants to do the labor and help secure the territory.”

As I ambled through the courtyard next to the chapel, the questions I’d sought to answer at the start of my journey surfaced.

Did the natives suffer more, or less, because of Serra and his legacy? For the natives who experienced the initial contact and agreed to baptism, the effect was traumatic: a forced adherence to a culture and religion they scarcely understood, the deaths of thousands due to disease, and the constant threat of corporal punishment.

“I am willing to admit that in the infliction of [flogging], there may have been inequalities and excesses committed on the part of the some of the priests,” Serra wrote, “and that we are all exposed to err in that regard.”

But by the time the next wave of settlers arrived, many of the surviving natives had learned Spanish and mastered trades like carpentry and weaving. They’d also learned that some form of assimilation was a matter of survival.

Serra’s historic relevance is less disputable. The Catholic faith remains a powerful force in California today. A third of the population identifies as Roman Catholic, the most of any denomination, and the Mission San Carlos that Serra founded is a jewel in the church’s scepter. His story is key in the Golden State narrative – likely because it’s preferable to look back on the settling of California through the lens of a man bringing God to the land, rather than the gold-crazed wave of immigrants who often brought calamity in their wake. His legacy continues to inspire the best in others, like the Franciscan Workers of Junipero Serra, who last week served 1,000 Thanksgiving plates at their Dorothy’s Place Kitchen in Salinas.

In 1985, Pope John Paul II declared Serra “venerable,” the first of the three steps to sainthood, and “blessed” in 1988, making him one confirmed miracle away from being declared a saint.

My take: The sometimes violent history and forced captivity of the missions doesn’t merit celebration. A premium on blind faith and suffering, meanwhile, seems like a medieval relic not worthy of imitation. Neither does flogging.

Still, in my mission, there was enlightenment that came through suffering, just maybe not the kind Serra sought. Whereas I stressed out about the reliability of my bike cables, Serra walked into new lands on a leg that would have sent me to the ER. The rigors of the journey exhausted me physically and spiritually, though I slept on beds and drank wine. And whereas I sought relaxation at the end of my hard days, Serra read, wrote, prayed, preached and worked nearly every minute he wasn’t traveling. He didn’t take shortcuts, through broccoli fields or otherwise. He may not be a saint, but his inexhaustible fortitude seems nothing short of miraculous to me.