From Arts to Eats: A Local Insider's Guide to Living in Portland's Best Spots

Hello! My name is Chad, and I am your ApartmentHomeLiving.com Local Expert for Portland, Oregon. After living in this one-of-a-kind city for more than 20 years, I have seen it change in many exciting ways. It has certainly grown over the years, yet it remains a cozy and close-knit community in many ways. But to fully appreciate the Portland of today, it may be helpful to briefly explore its history.

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The Origins of this Remarkable American City

Let me tell you, living in Portland means living with one foot in the past and the other in a pair of mismatched socks you bought at a craft market. In fact, those socks were likely handmade by an artisan using techniques that were common during Portland’s very earliest days.

Back in the 1840s, this place was just a muddy clearing along the Willamette River. That was before two New England traders (Asa Lovejoy from Massachusetts and Francis Pettygrove from Maine) decided to formally establish a settlement here. Lovejoy wanted to call it “Boston,” while Pettygrove argued for “Portland.” They settled the debate by flipping a coin. Pettygrove won two out of three tosses, and just like that we became Portland.

That mix of practicality and oddball charm is baked into Portland’s DNA. The early city was a rough port town full of loggers, shipbuilders, and drifters, but it always attracted people who colored outside the lines. When the railroad came through and the timber industry boomed, a series of new residents brought their ideas, their unusual hobbies, and a desire to do things their own way in this city of ambitious misfits.

Today, you can see the connection between that foundational coin toss and Portland’s love for groundbreaking indie music, naked bike rides, and donut stands shaped like unicorns. Portland has always chosen its own way, mixing a little haphazard luck with plenty of bombastic personality.

Portland’s Most Notable Neighborhoods

Because I have lived in quite a few Portland neighborhoods, I have seen how many different sides this city has. I’ve called both the East and West sides of the Willamette River home, and any Portland local will tell you these two sides can often seem worlds apart. The West side is known for its history and established institutions, while the East side is all about creativity and grassroots energy. Together, they show the full personality of Portland. No matter what side of the city they are on, a few neighborhoods stand out for what they offer and how they capture the city’s spirit.

The Pearl District

Back when I was in grad school at Portland State, I spent a lot of time in the Pearl District. It’s one of the city’s most recognizable neighborhoods and a favorite for Nike employees and other professionals who want to live nearby. Most people don’t realize how much it has changed over the years. Before the mid-1980s, it was an industrial area with rail yards, warehouses, and factories. After it was rezoned, artists moved into the empty buildings, and the neighborhood slowly became a cultural center. Now, it’s known for its galleries, boutiques, and modern condos and townhouses. It is also home to Powell’s City of Books, which is widely renowned as the world’s largest independent bookstore. It is also the site of Portland’s longstanding First Thursday: a community art event that features large numbers of street vendors and special attractions in galleries and shops.

St. Johns

The second-largest neighborhood in Portland according to square mileage, St. Johns boasts numerous historic landmarks, including a charming turn-of-the-century post office and a neo-Georgian city hall that now serves as a police precinct. The neighborhood’s National Cash Register Building is home to a pub and theater operated by McMenamins, a family-owned chain renowned for revitalizing historic spaces throughout greater Portland. The namesake of the neighborhood is the iconic St. Johns Bridge. In a city so full of bridges that it earned the nickname “Bridgetown,” the St. Johns Bridge is by far the most photographed and admired. On a personal note, I had the honor of officiating a beautiful wedding beneath its soaring arches in a nearby Cathedral Park.

Brooklyn

I lived in Brooklyn for about three years and ended up loving it more than I expected. It’s on the east side of the Willamette, between Reed College and downtown, and has one of the fastest routes across the Ross Island Bridge. But there’s more to Brooklyn than just convenience. The historic Aladdin Theater brings in both big-name musicians and local bands, and the Original Hotcake House is a classic spot where the pancakes are huge and the prices are always fair. I’ve eaten there more times than I can count. For something a little different, Edelweiss Sausage and Deli is probably the best place in Portland for real German food and specialty groceries. It’s the kind of place you find only if you live nearby or know someone who does.

Portland is full of great neighborhoods, and these three demonstrate the broad spectrum of practical benefits and attractive vibes available here. Each of these neighborhoods shines in its own special way. Together, they show how Portland keeps changing and growing while still holding on to what makes it unique.

Getting Around Portland

Getting around Portland really does feel like picking your own adventure every day. Sometimes I hop on my bike, other times I ride the MAX. And if I choose to walk, I might just stroll six blocks out of my way to get breakfast at my favorite coffee shop.

Our exceptional public transit system, TriMet, keeps the city moving. The buses wind through most neighborhoods and link up easily with our MAX light rail trains. The MAX offers stress-free rides from the airport into downtown or out toward the suburbs. It is not unusual to see someone knitting, reading a novel, or balancing a pink box of pastries on their lap during the commute.

Biking is a big part of life here, and Portlanders ride in every kind of weather. We have ample bike lanes throughout the city, and neighborhood greenways give riders quieter routes away from traffic. If you do not own a bike, the bike share stations scattered throughout the central city make it easy to grab one on the fly.

Portland is also highly walkable city. Our neighborhoods are packed with cafés, parks, and corner shops, so you can wander from one to the next without even realizing how far you have gone.

Driving is doable if not always easy or fast. Downtown parking can test your patience unless you already have a favorite side street or garage. A lot of locals will drive to one spot, park the car, and spend the rest of the day walking or riding transit. Portland rewards anyone who is willing to mix it up.

Touring Portland: The Destinations Even Locals Appreciate

If you’re in the downtown area, you can take either the MAX light rail or the Portland Streetcar directly to the downtown Park Blocks to take in many of Portland’s most important cultural destinations. Visitors and residents alike flock to the Portland Art Museum to enjoy a broad spectrum of permanent and touring exhibits. The Park Blocks are also home to the Oregon Historical Society Museum, where you can see the very penny used in the coin toss that decided Portland’s name.

From there, it’s just a short trip to the Oregon Zoo, the Portland Japanese Garden, the Hoyt Arboretum, and the International Rose Test Garden. One glance at the Rose Garden, and you’ll know why Portland is called the “City of Roses.” Every summer, this garden fills with crowds eager to enjoy it seemingly endless rows of blooms in a dazzling array of colors.

Any basketball lover lucky enough to see the Trailblazers at the Chiles Center is unlikely to be disappointed. But for local sport fans, Providence Park has become one of the liveliest places in town. This is where the Timbers and Thorns play, and these two teams have transformed Portland into a true soccer town. The stadium also hosts concerts and other events, but it’s during soccer matches that the energy is at its peak.

For another kind of family-friendly thrill, the Portland Aerial Tram is hard to beat. It connects the South Waterfront to the Marquam Hill campus, where OHSU Hospital and Doernbecher Children’s Hospital are located. Even if you are not headed to an appointment or a shift, the tram is worth the trip. As it climbs about 500 vertical feet, you get sweeping 360-degree views of the Willamette River Valley, downtown Portland, and the surrounding hills. Locals treat it as both transportation and sightseeing, and it serves as the crown of the South Waterfront area.

But, as someone who loves to hike, I’m most drawn to Portland’s parks and wild spaces. Mount Tabor is a favorite of mine, with its winding trails, old reservoirs, and wide views of the city. Forest Park is another highlight. Covering 5,200 acres, it’s one of the largest urban forests in the country and has enough trails to keep you exploring for years. Powell Butte is also worth a visit. From this grassy plateau, you can enjoy sweeping views of Mount Hood and the Cascade Range.

One of the Best Food Cities in the US

Portland is internationally recognized for its exceptional restaurants, and its food scene is every bit as unpredictable and offbeat as the city itself. Voodoo Doughnut serves as a prime example. Far more than a donut shop, this spot is a full-blown Portland institution. When it burst on the scene in 2003, it changed the donut game with unconventional toppings that ranged from cereal to bacon. The Voodoo Doll donut is practically a local celebrity. Locals may grumble about its long lines, but the pure spectacle of it all is nothing if not compelling. Grabbing a Voodoo donut is basically a rite of passage in Portland.

If you’re in the mood for something a little more adventurous, Le Pigeon is my go-to spot when I want to treat myself. The food here is as inventive as it gets, and the cozy, bustling dining room has that signature Portland energy (equal parts chaos and charm). Whether it’s foie gras profiteroles or some surprise from the ever-changing menu, each plate feels like a little adventure.

When I’m craving something that feels like a warm hug but still packs a punch, Swagat is my standby. The curries are always just right, the naan comes out warm, and the whole place has that welcoming, come-as-you-are vibe. It’s the sort of spot you find yourself returning to, night after night, because it just feels like home.

For a comfortable lunch or a weekend breakfast, I always find myself at Dots Café. It’s small, unpretentious, and extremely cozy. It’s the kind of place where the staff knows the orders of regulars before they sit down. The pancakes, omelets, burgers, and sandwiches aren’t necessarily fancy, but they certainly hit the spot!

What I love about Portland’s restaurants is that each one has its own distinct personality. Whether you’re in the mood for experimental cuisine, international flavors, or just classic comfort food, there’s always a spot that feels like it was made for you.

Keep Portland Weird!

From its very earliest days, Portland has been a magnet for offbeat innovators who want to do things differently. I was drawn here from the Midwest, and Portland’s many diverse communities, unique cultural offerings, and exceptional restaurants continue to surprise and delight me.

Many of the supposedly negative things that you have heard about Portland are certainly true. For example, you can expect a steady rain that stretches from late spring to early autumn every year.

However, Portland’s various challenges have ultimately made it what it is today: a city full of ambitious iconoclasts that don’t mind a little drizzle. And its long rainy season is only one of the many unique local qualities that continue to keep Portland weird!