The largest and most populous city in Oregon, Portland won its name in a coin toss, when landowners Asa Lovejoy and Francis Pettygrove both wanted to name the new settlement after their hometowns—Boston, Massachusetts, and Portland, Maine, respectively. Pettygrove obviously won, and the famous penny now resides at the Oregon Historical Society in downtown Portland.

Basing a major decision on a coin toss feels apropos for a city known for being eccentric with a decidedly live-and-let-live mind-set. This eco-conscious hotspot caters to everyone from outdoor adventurers to live music fans to foodies who are as interested in cheap food-cart eats as they are in gourmet farm-to-table fare. Portland is chock-full of hipster vibes, cozy coffee shops, and pockets of community scattered throughout its neighborhoods.

After checking in to Hotel Lucia in downtown Portland, my first order of business was food, and a stool at the bar at Bamboo Sushi beckoned. So did the specialty vegetarian roll called Green Machine, a tantalizing combination of tempura-fried long beans and green onion, topped with avocado and a cilantro sweet-chili aioli. This hip restaurant not only serves up delicious sushi but also became the world’s first certified-sustainable sushi restaurant in 2008, ethically sourcing fish from plentiful populations and reducing its carbon footprint.

After my meal, I Ubered to Southeast Portland to the Clinton Street Theater. This charming single-screen venue—which features a popcorn machine in its tiny lobby—is one of the oldest movie houses in the country, and it frequently works directly with independent filmmakers. On this particular night, the documentary Flamenco Syndrome was premiering. I purchased my ticket and some gummy worms (total price: a very reasonable $7.50) and found a seat. Flamenco Syndrome is Bijoyini Chatterjee’s first feature-length documentary, and she even Skyped in for a virtual question-and-answer session after the viewing.

Patrons stood around outside the theater talking to each other as I Ubered back to my neighborhood for a late-night bite at Petunia’s Pies & Pastries. The vibe in the evening is all dimmed lights and lit candles, and I happily dined on vegan mac and cheese and a slice of turtle cheesecake before calling it a night.

There are two restaurants I never miss when I visit Portland: the previously mentioned Petunia’s and Harlow, a hipster bohemian spot on Southeast Hawthorne Boulevard, located east of the Willamette River. This morning I opted for the Farmer’s Vegetable Scramble: farm-fresh eggs scrambled with roasted root vegetables, spinach, and kale in a creamy chipotle cashew hollandaise over quinoa. I found a seat in a sunny window nook and people-watched as I savored all the flavors and textures of brunch. Portland really knows how to do healthy cuisine well, and Harlow, in particular, partners with over a dozen local vendors to create not only a pleasurable eating experience but also a community-minded one.

Fueled up and ready to take on the day, I took an Uber another ten minutes east to the Monticello Antique Marketplace to hang out and draw with the Portland Coffee and Sketch Club, an artists’ gathering that meets in different venues around the city. This week’s challenge was to sketch a scene from one of the many vignettes at the antiques mall. I found the group in the back corner of Monti’s Café spread out across three tables that were nestled among bookshelves overlooking the antiques. The vibe was relaxed and casual, and the group included beginner artists, a woman working on her first graphic novel, an aspiring actor, and a professional caricature artist.

My sketch tucked away to be finished with some paint later, I made my way to the Portland Mercado in Southeast Portland to meet my friend, Huyen, for an early dinner. This colorful public market place was created to support and grow Latino businesses and serves as a hub for Latino culture and community. Opened in the spring of 2015, it’s a combination of outdoor food trucks and indoor businesses. Huyen and I made a beeline for Tierra del Sol, a food truck owned by Mexican-born Amalia Sierra. A few minutes later, we had plates full of tacos—veggie for me, carnitas for my friend. Impending storms meant we found our way inside and joined other diners at community-sized tables. There we found an exhibit that details the chronology of Latino entrepreneurship in Portland, an important educational display at this cultural hub.

With some room in our stomachs for dessert, we decided to check out Little Chickpea in the Pearl District. A new concept in dairy-free “ice cream,” Little Chickpea’s is made from chickpeas, as the name suggests. We sampled four out of the eight flavors: Cherry Chai, Lemon Ginger, Cold Brew Coffee, and Mint Matcha. The airy, industrial-style space also features an open kitchen where the “ice cream” is made.

It was nearing sunset, and one of my new drawing pals had tipped me off to a popular Portland event in Northwest Portland called the Swift Watch. When Huyen and I arrived at the side lawn of Chapman Elementary School, people were spread out on blankets and volunteers from Portland Audubon were behind a booth answering the questions of curious onlookers. As the signs on the side lawn of the school explain, “Each September, thousands of Vaux’s Swifts congregate in the chimney of Chapman Elementary School before they fly south for the winter. Just before dark, the swifts amass above the school in a huge spiral formation and fly into the chimney to roost, giving the impression of an avian whirlpool.” Unfortunately, the rain earlier that evening meant the swifts got cold and flew into the chimney before their usual time. We saw several small groups of swifts, but we had to resort to a YouTube video to get the full effect.

To warm up our bodies from the chilly, rainy night, we drove downtown to the Portland City Grill, renowned for its stunning views of the city from its thirtieth-floor perch. The place was appropriately packed for a Saturday night and the coveted nooks near the windows were all occupied, so we sipped elderflower cocktails at the bar as we gazed around at the well-dressed crowd.

After a brief interlude to change into fancier clothes, I met back up with my friend at Tango Berretin in Southeast Portland. This venue, which typically hosts Argentine tango events and classes, looks like it was lifted from a European street, with its whimsical mural painted on the side of the building and string lights and white café curtains beckoning onlookers to wonder what magic is happening within. Once inside, the charming quirkiness increases, with tango stilettos in an assortment of styles glued to the ceiling and a whole wall framing the drinking fountain devoted to empty Altoids tins. Tonight, the event was Milonga 24, and dancers embraced each other to the sounds of the old tango orchestras being thoughtfully deejayed off a laptop.

I woke up to drizzle and wind, and it took some mental effort to drag myself out of my warm bed and into the cold. After breakfast at Petunia’s, I hopped across the street to the Never Coffee Lab. This place is so darn aesthetically pleasing, with a splashy abstract mural on one wall, framed art by the talented Shiela Laufer on another wall, and a display of bagged coffee in a rainbow of colors. It’s known for its specialty lattes, which are described in great detail on oversized business cards perched on a wooden tray like Scrabble tiles. I chose the Hunny, featuring flowering jasmine, dark chocolate, and wildflower honey.

Portland is known for its 37,000 acres of green spaces, making the city feel more like a leafy oasis than an urban jungle. However, the rain meant my previous outdoor itinerary of strolling the Portland Japanese Garden and surveying the grounds at the Pittock Mansion needed some modifications.

So I headed back to Southeast Hawthorne Boulevard to check out some of the shops I had seen when I was eating at Harlow the day before. Red Light Clothing Exchange is a great place for vintage pieces, ranging from everyday T-shirts to Twiggy-worthy dresses from the 1960s. The next stop was ORO to browse hipster-chic jewelry laid out on wooden tables in a pleasingly minimalist shop that felt friendly and affordable. Tender Loving Empire caught my attention with clever art prints strung up on the walls and great music playing. Tender Loving Empire is actually a record label for most all of the artists showcased in their shop. In the back is a niche devoted to vinyl, which requires you to pass by displays of adorable baby onesies and hand-sewn baby toys in the shape of clouds. And finally, the House of Vintage is worth a visit just for the sheer size of the place. According to online building records, this behemoth of a space, built in 1918, was once an auto-service shop and then became the Rose City Paper Box Company in the 1950s. It’s a collective of vintage vendors now, and you will often hear the voice of a Zoltar fortune-telling machine (like the one in the movie Big) ring out.

I wrapped up my trip with a late-night visit to Powell’s City of Books, five blocks from my hotel, in the Pearl District. This place, founded in 1971, is an institution, and you can’t help but feel like you’re part of a vast community of readers and lovers of bookstores. Huyen met up with me, and I suggested we play a game where one person asks a question and the other person closes his or her eyes and points to a book.

“What would the universe like me to know?” I asked. Huyen grabbed Mrs. Vargas and the Dead Naturalist, the book I had blindly gestured to, and flipped it over. “This is a book of wonders. Each story unfolds with humor and simplicity and perfect naturalness into something original and totally unpredictable,” Ursula K. Le Guin had written in her review of Kathleen Alcalá’s novel.

Portland is indeed filled with simple wonders, many of those in the form of the communities I saw—like the filmgoers, the Latino business owners, the health foodies, the artists, the bird-watchers, the dancers, the baristas, the makers, and the readers.

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