In April, something odd happened to the Jewish population of Portland, Ore.: It nearly doubled.Where once everyone in town had long believed in a rough estimate of 25,000 Portland Jews, suddenly a new, far more accurate count was on people’s lips: 47,500. “The Federation did this census,” said University of Oregon historian William Toll, referring to the Jewish Federation of Greater Portland—which, to help serve this proudly weird, exceedingly non-religious city, decided two years ago that it needed a better count of its target audience. This survey was the first serious census of Portland Jews in decades, Toll said, and when the final results came out in the spring, “lo and behold, there were twice as many Jews in Portland as they thought were there.”“People were stunned,” Marc Blattner, president and CEO of the Federation, told me. And a mystery was born. Toll mimicked the reaction of Federation leaders: “Who are they? Where did they come from?” The answer? “They don’t know.”So, one day late in the summer, I pumped up the tires on my bike, told my Seattle friends I was off to look for the Lost Tribe of Portland, and boarded an Amtrak train heading south.“Bridgetown” is one of Portland’s best-earned nicknames—there are eight major bridges in the central business district—but another way of looking at things is that Portland is a city sliced in half by a river. This particular geography is key to understanding the lay of the Jewish land in Portland. The cold, snow-melt-fed waters of the Willamette River run through the middle of the city, flowing northward toward the bigger Columbia River and then out into the Pacific. It’s picturesque, but it cuts Bridgetown into its distinct western and eastern sides, and it divides the Jewish community, too.The Jewish establishment in Portland—the oldest synagogues, the Federation headquarters, the Federation’s best donors, the more buttoned-up crowd—can be found in west Portland. The “Lost Tribe”—a mass of younger, less affluent, largely unaffiliated Jews who turned up in the Federation’s new census—can be found mainly in the city’s eastern half. Hence, one major conclusion of the Federation’s census: Jewish leaders in the city need to begin more outreach, “especially on the east side,” the survey states, to engage this previously unknown, presently underserved mass of Jews.“We know that they’re people,” the Federation’s Blattner told me. “They’re regular people. But what they want and what they’re interested in is the question.” Another study, this one focused exclusively on the east side, is in the works. In the meantime, the Federation is putting about $300,000—or 10 percent of its annual campaign—behind events like the one I’d come to Portland to see.***It was a Friday evening in late July. As the sun was going down I left the Amtrak station in west Portland and headed east, pedaling up a ramp onto the red steel-trussed Broadway Bridge, then over the Willamette River, and finally up a steep hill to Overlook Park. Under a giant ash tree: a pile of bikes laid down by locals who, like me, had ridden rather than driven to “Shabbat in the Park.”About 150 Portland Jews were there, picnicking in golden light filtering down through the leaves of the big tree and creating a beautiful, classically Northwest scene—one that also made for easy allusions to the Tree of Life and the Garden of Eden. The rabbis presiding over the event did not miss the opportunity and made those exact allusions as participants flipped through a three-page, stapled prayer service that included English translations (and transliterations) for the Hebrew prayers.“You may not know this, but it’s the Jews who invented TGIF,” Rabbi Ariel Stone told the crowd. She leads Shir Tikvah, the cosponsoring synagogue for the event. Founded in 2002, it’s the only synagogue on the east side of Portland and currently shares sanctuary space with a United Church of Christ. “We daven in our Birkenstocks and our jeans,” Stone told me, speaking of her congregation. “We do yoga. We’re vegans.”Stone told the crowd that night: “It’s not important where you belong. All that’s important is that you belong. No one ever has to be alone in this world.” Amid drum- and guitar-playing, there was talk of mindfulness and intentionality and suggestions that Judaism could be freer of guilt and neurosis. Rabbi Brad Greenstein, of the west side’s Congregation Neveh Shalom, which helped organize the event and is the oldest Conservative synagogue on the west coast, explained the purpose of the evening as “outreach toward unaffiliated Jews.” He spoke to the crowd about abandoning iPods and other technology, at least for a moment, and “tuning our souls to the frequency of meaning.”There were a few yarmulkes in the crowd, but mostly it was uncovered heads. A man in a Utilikilt held a young girl in a pink dress. A woman danced with her daughter, who was shaking a steel reusable coffee mug like a rattle. I spotted one lonely bucket of fried chicken, but mostly, the picnic blankets were laden with salads—bean salads, fruit salads, bagged salads, orzo salads—in pots and bowls brought from home so as not to waste Tupperware. And, of course, challah.Everyone looked great, the picture of relaxed, locavore health, a reminder of the well-known joke from the television series Portlandia—starring Carrie Brownstein, perhaps one of the city’s best-known Jews—about how progressive, affordable Portland is “the city where young people go to retire.” Except there was just one problem: This was not a crowd filled with young people, retired or otherwise.In fact, it was overwhelmingly made up of middle-aged west-siders. Rabbi Greenstein thanked people for making the “schlep” over from the west side of the Willamette, and a woman I was seated with told me she saw mostly familiar faces from that side of the river. This made it very easy to spot the few young east-siders—three of them: a young man, his wife, and their 4-month-old daughter—because they looked so out of place.***David Michaelis, 31, who lives in Northeast Portland, works at a financial services firm where he specializes in Internet technology. For “Shabbat in the Park” he was wearing a “Jews Kick Ass” T-shirt featuring pictures of Albert Einstein, William Shatner, Jesus, the Fonz, and Sammy Davis Jr. “I’m not too involved,” he told me, munching on Bing cherries and snap peas toward the back of the crowd beneath the ash tree. His wife, Kerry, who was with him, was raised Catholic, not Jewish, making Michaelis a prime example of one of the Federation’s census findings: Less-involved Jews in Portland are “more apt” to be living with non-Jews. In a twist that shows just how confounding the young Portland east-siders can be to the west-side establishment that wants to reel them in, it was Michaelis’ non-Jewish wife who brought the family to Shabbat in the Park. “She likes the open-minded thing,” Michaelis told me. Also on his wife’s list of likes: the music, that the service is mostly in English, that the whole thing is outside. (From the census preparers: “Given the fact that this audience is most likely to be living with non-Jews, consider development of more secular events or programs that are welcoming and accepting of non-Jews.”)Michaelis goes to synagogue only on high holidays—“And my grandmother would be pissed if she read that, so put that in,” he said—and while he told me that Shabbat in the Park was “pretty cool,” he quickly added: “If there were more people my age here, I’d be able to socialize more.” Gesturing to the crowd, he continued: “These people are older than us—way older than us.” He then pointed at a nearby woman. “I mean, this lady could be my grandma,” he said. Because Michaelis works, has a young family, and plays on a basketball team, he lamented, “I can’t go play beer pong on Wednesday at the Moishe House.” (A Moishe House, sensing opportunity, just opened in east Portland.)So, the question remains: What, exactly, would Portland Jews like Michaelis rather have offered to them? “We just wanna get together and hang out,” Michaelis said.***That may sound perplexingly vague, but it’s very much in keeping with present national trends, as well as historical attitudes in this particular region. There is a long tradition—and not just in Portland—of Pacific Northwest Jews being a bit unusual in their disposition and practices, a bit harder to pin down than Jews from other parts of the country. University of Oregon’s Toll co-wrote a book on the subject in 2009, titled Jews of the Pacific Coast, which chronicles the rich history of Jews in the area and describes their migration as “a process of self-selection that favored the less insular and the more daring.”Jewish merchants, for example, were a part of the early growth of major Western cities like San Francisco and Seattle, especially after the Gold Rush kicked off in 1849. “They tended to be a different kind of person,” Toll told me. Independent-minded, ready to leave the community they knew, more connected to natural beauty than, say, the Jews who declined to leave urban centers of Philadelphia and New York for an unknown life among the evergreens and people who at the time were called Indians. In the tiny Oregon Jewish Museum (located on the west side of the Willamette, of course, not far from the fortress-like Temple Beth Israel, founded in 1858) one can find pictures of these early Oregon Jews, riding horseback and walking the rugged beaches of the Pacific Coast.Today, said Blattner, of the Federation, Portland is seeing a new wave of migration by adventurous and independent-minded Jews. “It’s a hot city,” he told me. “A hidden jewel.” He’s heard the joke, of course, about Portland being the place where young people go to retire—or, put in less jokey terms, the place where young people go to ride out the Great Recession in cheap, comfortable style, with the thought that they’ll also be involved in building a new, less materialistic, more do-it-yourself kind of urban American culture. But Blattner also sees a fundamentally different philosophy prevailing in Portland than on east coast, one that’s very alluring.“There is a mindset that people do their jobs, and at the end of the day they want to go hike, bike, or enjoy the outdoors,” Blattner said. “And that’s a beautiful thing.” Plus, he added, “We live in this very open, progressive society where everything is all, ‘Be what you want to be,’ ‘Live your life.’ ”For the unaffiliated Jews identified in the Federation’s census, however, the strong embrace of this nice Portland ethos is helping to create a disconnect. They’re not the previous generation’s Jews, and this rings out in the census findings. For example, unaffiliated Jews in Portland see Israel as a much lower priority than the city’s older establishment Jews, the survey found. The unaffiliateds are more interested in “promotion of civil rights and tolerance” than the Jewish establishment is; they’re also more interested than their older counterparts in “economic justice” and “protection of the environment.”Even if these unaffiliated Jews had money for a membership at a synagogue—which many don’t—they are far less interested in institutions, or even institutional-feeling things, than the established core of Portland Jews.Toll sees all of this as part of a trend that’s much bigger than just Portland, part of an ongoing breaking-apart of old norms for what it means to be Jewish. “Jews don’t identify as Jews in the way they used to,” Toll said. “We’ve become Americanized. And our concept of being Jewish is largely through religion, and religion seems to mean a way of finding spiritual meaning in our lives, and that seems to mean being on some spiritual quest, rather than being affiliated with some institution.”Jonathan Sarna, a professor at Brandeis and a leading scholar of Jewish history, agrees. He says that intermarriage, the general decline of Judaism’s Conservative movement, and a rise in more complex notions of identity have all contributed nationwide to “this large, less visible, maybe invisible group of Jews that, unless something is done about it, are going to disappear.”Sarna is not surprised that Portland Jews may have been undercounted for years. “We don’t have good national data anymore,” he said, explaining that national Jewish groups abandoned conducting similar censuses, due in part to cost and arguments over methodology. What surprises him is the Portland Federation’s reaction: pouring money into learning more about, and reaching out to, these unaffiliated Jews. “A lot of Federations have had trouble justifying this kind of investment,” Sarna said. “After all, these young unaffiliateds are not giving much to the Federation and profess not to care very much about the Federation.”Blattner, the president of the Portland Federation, sees it as an investment in people who will, if all goes well, become future donors—“a short-term loss for what we hope is a long-term gain,” as he put it to me.Sarna called Blattner’s strategy refreshing. “It may be that Portland could be a place that will test out new models of what a Federation could be, that Portland could be something of a laboratory for new efforts to engage these less-affiliated young Jews.”Blattner, for his part, is already there, talking passionately about “Jewish life without walls,” speaking of “changing the language in Jewish life to one that normal people understand,” and saying that, above all, “what we want to do is recognize that to be Jewish does not have a single definition.”***The morning after Shabbat in the Park, I woke up early in west Portland, put an iced coffee in my bike’s water-bottle cage, and rode over the Willamette River again, this time across the green-beamed Hawthorne Bridge, headed for Sellwood Park in southeast Portland. The event: Shabbat in the Pool.Again, a lot of people at the event had, just like me, commuted over from the west side. There were about 100 of them, mostly families with kids, gathered on a slowly warming Saturday morning to jump in the pool, listen to guitar music, and be led in song by a megaphone-holding Deborah Eisenbach-Budner of the Reconstructionist community Havurah Shalom. When the splashing and singing was done, she led them to a picnic area for lunch and storytelling. (“Gluten-free challah!” she shouted into a megaphone.)Again, it was easy to spot the very few young east-siders at this event, which was partly geared toward young east-siders. Joshua Fingert, 29, a barista and espresso-machine mechanic, was there with his wife, Michelle Lamanet, a stay-at-home mom; their son, Uzi, 3; and all the supplies a young Portland family might need on a morning like this one: swimsuits, sunscreen, carrot and cucumber slices, snap peas, hummus, fresh berries. Joshua was raised Conservative but doesn’t belong to a synagogue and told me he sees himself as culturally Jewish. (From the survey: “Unlike highly and moderately involved Jews, most Jews with low levels of involvement define their Jewish identity as cultural.”) Michelle isn’t Jewish, but she went to a Jewish mother’s circle while pregnant with Uzi, and their family observes High Holidays, keeps Shabbat most weeks, and even makes their own challah. “We’re still kind of finding our niche,” Michelle told me, speaking of their place in the Portland Jewish community. “The main barrier, for us, is money in joining a synagogue. If it was free, totally.” But it’s not, and they weren’t aware of the programs that do exist that could subsidize or waive their membership fees.Josh and Michelle appeared to be the youngest parents at the event. They didn’t know any other families there, and that didn’t surprise them. Though they have a lot of Jewish friends, those friends generally don’t have kids, which means there’s not much reason for those friends to show up for an early Saturday morning kids’ pool party.This, said Caron Rothstein, community engagement director for the Federation, is a vexing challenge. We were standing poolside as Rothstein, wearing a shirt that read “Happy Challah Day,” talked about the growing gap in time between a person’s bar or bat mitzvah and his or her decision to raise a family—part of a general social trend of Americans getting married later, having kids later, delaying all the things that used to cause many of them to naturally connect with Jewish institutions in their 20s or early 30s. Now those life events often don’t happen until a person is in his or her mid to late 30s, or even 40s.Young, single, unaffiliated, 20-to-30-something-year-old Jews living on Portland’s east side are doing what young, single, unaffiliated, Jews of that age do—and they remain, essentially, lost to the Federation. “The challenge is finding things that resonate for them and that speak to where they are in their life mentally and physically,” Rothstein said.To Sarna, this is very familiar. “A new development stage has come about,” he told me. “Some people have called them ‘the Odyssey years.’ But it’s a totally new phase. Which is why we have so few Jewish institutions to deal with it.” He suggested one answer may be to encourage young unaffiliated people who feel only partly Jewish—or identify as just culturally Jewish—to at least feel that “their Jewishness is the most precious part of their identity.”Toll, the historian, had a similar suggestion, saying people like Rothstein and those running the Portland Federation should cultivate new outreach efforts by asking a simple question: “What is Jewish about the young people they’re trying to reach?”It may not be that easy. When I got back to Seattle, I called Michaelis, the 31-year-old east-sider who I met at Shabbat in the Park, and asked him: What’s Jewish about you?His answers contained a lot of the familiar, complicated sentiments that tend to confound establishment Jews who are used to a simpler version of Jewish identity. Michaelis said his connection to his Jewish family makes him Jewish, though he doesn’t want to practice the way his Jewish family does. He also said his Judaism is more about being part of a culture than being a member of a religion. Finally, he suggested that Portland’s Jewish establishment try getting involved in promoting “Portland scene stuff—going to a bar, having drinks” if they want to reach him and other members of his particular tribe.Michaelis does, however, know the answer to the question of what, exactly, he wants from Jewish life. It’s just that it’s still more of a vague notion than the kind of roadmap the Federation is seeking. “For me,” he said, “it’s all about being around people who are Jewish.”Eli Sanders is an associate editor at The Stranger and the winner of the 2012 Pulitzer Prize for feature writing. His website is www.elisanders.net.