Boly:Welch’s Unofficial, Unauthorized Guide for Moving to Portland

Portland Oregon metro glows with light at dusk while Mount Hood watches over

For our unofficial, unauthorized hot take: Portland is a great place to live. And lots of people agree with us! We added almost 20,000 new residents from 2018 to 2019, most of whom moved here from other states. That’s almost 54 new neighbors per day. 

In the last decade, 400,000 people have set down roots here, drawn in by economic opportunity and greater work-life balance. Over half of those new residents settled in one of Oregon’s three most populous counties — Multnomah, Clackamas, and Washington — which combined make up the Portland metro area. 

At Boly:Welch, we’ve definitely experienced a swell of out-of-state candidates with questions about relocating to Portland. Some of the more common inquiries: Where should I live? How do I get around? What is there to do? Where are the best places to eat? 

If you’re reading this guide, you’re likely new to Portland or considering a move to the Rose City. With that in mind, we’ve put together a practical, semi-comprehensive guide to Portland that will make your relocation as smooth as Damian Lillard’s 3-pointer (note: if you missed that reference, it’s about Dame Time to skip down to the sports section). 

It’s a Wonderful Day in the Neighborhood

There is no wrong place to live in Portland. There, we said it. That being said, you’ll hear a lot of opinions about different neighborhoods, because where you live does have a sizable impact on how you move about the city. Although the Portland metro area is fairly contained, especially compared to urban sprawls like Los Angeles and Phoenix, we still have the unfortunate problem of having some of the worst traffic in the nation. So, that four-mile commute into downtown that didn’t look so bad on Google Maps can end up being an hour-plus depending on where you choose to live. But on the plus side, we also have a fairly reliable public transit service (TriMet) that sprawls across the three major counties. 

There is also hot debate on the perks of living on the east or west side of Portland, although the pros and cons depend on your own personal preferences. The eastside tends to be a little more urban, with trendy dining and shopping options, while the westside has a reputation for being more suburban and better for raising families. Of course, these are broad generalizations, and each “side” has neighborhoods that fit neatly into each category. 

Portland is also divided roughly into six major areas (N, NE, SE, East, NW, SW), primarily split up by the Willamette River (which divides east from west) and Burnside St (which divides north from south) and often referred to as “quadrants” despite there being more than four of them. You’ll often hear people referring to their quadrant colloquially as ‘Northeast’ or ‘Southeast’, before they specify a street or landmark. Generally, people often refer to their neighborhood by the nearest commercial street (e.g., Belmont) versus the actual neighborhood name (e.g. Sunnyside). So, you might hear something like: “I live in SE, right off Belmont,” when people are trying to orient you. 

Hand drawn illustration of Portland Oregon divided by neighborhoods and rivers

The Portland metro is made up of many smaller neighborhoods, each with its own flavor. There is no one perfect neighborhood, but you will find that some areas may match your lifestyle better than others. Here is a quick breakdown of each area with a few highlights:

A diverse mixture of residential, commercial, and industrial areas. Historically was the heart of Portland’s Black community, but has experienced rapid gentrification in the last decade or so, especially with the expansion of the Yellow Line MAX (our local light rail service) up Interstate Avenue. Easy to walk, bike, and catch public transit around town. Notable areas within North Portland are: Mississippi Avenue, Killingsworth Street, St. John’s, and Kenton. 

Some of our favorite finds in the area are: Skidmore Bluffs, Overlook and Peninsula parks, Po’Shine’s Café De La Soul, La Bonita, Sparrow Bakery, Victoria Bar

A large mix of smaller neighborhoods and housing, split further between the more affluent inner section – “close-in” – and the more ethnically, culturally, and economically diverse outer Northeast. Includes Alberta Arts District, Lloyd Center, Moda Center, MLK (again, site of major gentrification and displacement of Portland’s Black community), and Hollywood. Housing ranges from newly-built apartment complexes, to quintessential craftsman homes, to 1920s deco-style apartments. Parts of the area are very accessible by the Blue and Red Line MAX, frequent bus lines, and biking. Other parts are much more disconnected, especially in the outer NE areas. 

Some of our favorite finds in the area are: McMenamin’s Kennedy School, Grant and Irving parks, Hollywood Theater, Side Yard Farm and Kitchen, Woodlawn, Shady Pines, Hollywood Vintage, Wonder Ballroom

Like NE Portland, Southeast Portland stretches from the Willamette River in SE to roughly 82nd Avenue. It’s a mix of industrial areas, green spaces (including a wildlife refuge!) and large swaths of housing. Especially close-in, the area is accessible by major streets, which are chock-full of restaurants, bars, vintage shops, grocery stores, and more. You’ll likely hear about: Hawthorne, Stark, Belmont, Division, Powell, Woodstock, Mt. Tabor, Sellwood and Foster-Powell. Parking can be difficult – the streets are narrower than you might be used to – so your best bets are buses and bike lanes. The Orange MAX line will get you between SE and downtown Portland in a snap, if you prefer public transit to driving. The Portland Streetcar runs north-south along MLK Blvd, connecting you to NW Portland as well as Portland State University. 

Some of our favorite finds in the area are: Oaks Bottom, Woodstock, Cartlandia, Crystal Springs Rhododendron Garden, Aladdin Theater, Revolution Hall 

East Portland is commonly thought of as the area between 82nd Avenue and Gresham. It’s one of the most racially diverse areas of the city, as many displaced residents of color moved east of 82nd after their neighborhoods gentrified. The area has been chronically underinvested in, but there are a dearth of parks, sidewalks, streetlights and community spaces. The food scene is incredible and the area has a reputation for affordability. 

Some of our favorite finds in East Portland are: Powell Butte, Ding Tea, Birrieria La Plaza

Northwest Portland is where most visitors to Portland land, since it includes many of Portland’s hotels, boutiques, and large chunks of downtown, including the famous Powell’s Bookstore. It’s densely populated (in Oregon terms), mainly with apartments of all shapes and sizes. You’ll probably hear about the Pearl District, the Alphabet District (including NW 23rd Avenue), the Brewery Blocks, Slabtown, and Forest Park. If you want to settle down in this area, expect to pay for it. However, the tradeoff in accessibility and “downtown living” might be worth it to you – as long as parking isn’t a top priority. 

Some of our favorite finds in NW Portland are: Forest Park, Lan Su Chinese Garden, Ground Kontrol, Roseland Theater, White Stag sign

The majority of downtown Portland is located in Southwest Portland, which includes the Park Blocks, Tom McCall Waterfront Park, Pioneer Square, and many of the city’s prominent cultural touchstones like the Arlene Schnitzer Concert Hall, Portland State University, Pioneer Courthouse Square, the Portland Art Museum, and much more. The SW also expands – you guessed it – west to Oregon Health & Science University (OHSU)’s campus, the Lewis & Clark College campus, Washington Park (which includes the Oregon Zoo, International Rose Test Garden, Hoyt Arboretum, and Children’s Museum, to name a few). The downtown section is extremely walkable, but housing is mostly limited to dorm-style apartments. There are several semi-suburban neighborhoods (or at least neighborhoods with mini downtown areas), including Multnomah Village and Lake Oswego, outside of the downtown area that are considered great for families and decently accessible. Transit options outside the Blue Line MAX and some key bus lines are more limited, but parking is generally good. Housing options tend to be pretty pricey though, and limited outside of home ownership, except a few large apartment complexes. 

Some of our favorite finds in SW Portland are: Council Crest, Tryon Creek State Park, McMenamin’s Crystal Ballroom, Mill Ends Park, PSU Farmer’s Market, Providence Park


Hillsboro resides in Washington County, boasting both residential areas and farming communities. It’s also become a tech hub (colloquially known as Silicon Forest) with companies like Intel, IBM, HP, and more setting down roots here. Ever heard of the Airplane Home in the Woods or Roloff Farms? Yep, you can find both of those here. Housing in Hillsboro tends to be much more reasonably priced, and you can always rely on TriMet’s Blue Line to get you to and from downtown Portland.

Some of our favorite finds in Hillsboro: Orenco Woods Nature Park, Rock Creek


Beaverton sits just west of Portland in Washington County and is one of the most diverse cities in Oregon, with large African-American, Asian, and Latino populations. It’s home to Nike and more than a few shopping malls and natural areas. There are a lot more housing options, and Beaverton definitely has that ‘family-friendly’ feel, but since it’s such a sprawling area, you’d be trading affordability for convenience in terms of getting around town. If you’re commuting to Portland often, count on a slightly longer trip, but public transit via the Blue and Red Line MAX, WES Commuter Train, and various bus lines are consistently a good way to go. 

Some of our favorite finds in Beaverton: Uwajimaya, Beaverton Farmers Market, Tualatin Hills Nature Park, Nak Won, Frank’s Noodle House, Boriken


Gresham is in East Portland and is probably the most scenic city of the ones we’ve mentioned thus far. With a ton of parks, nature trails, and incredible views of Mt. Hood, there are plenty of activities for outdoor lovers. Housing tends to be more abundant and less expensive in this residential community, with more opportunities for first-time homebuyers to settle down. A diverse population including many immigrant communities make this a cultural hub for activities, events, and incredible food.

Some of our favorite finds in Gresham: Oxbow Regional Park, Gresham Japanese Garden, Powell Butte, Mt. Hood Theatre, Springwater Trail

A photo collage of Portland Oregon including bicyclists, street fairs, a Portland Trail Blazers basketball game, Peninsula Park Rose Garden, and Multnomah Falls

What to Do

Portland is a hub for many outdoor activities and has a buzzy cultural scene. It is also known for its rich and relatively varied food scene. In fact, if you start typing “Portland is known for…” in a Google search, it will inevitably populate with food and drink suggestions. 

So, if you’re looking for things to do, in no particular order or importance:

  • Check out the Rhododendron Gardens
  • Walk up Mt. Tabor on a clear day to see some great city views
  • Experience the calming side of nature at the Portland Japanese Garden
  • Witness the color explosion at the Tulip Festival in Woodburn (a 45-minute drive from Portland)
  • Embrace your curiosity at Design Week Portland
  • Sample some unique eats during Portland Dining Month
  • Kick off the summer at one of the many Rose Festival events
  • Support Portland’s vibrant small business community at My People’s Market or the PDX Night Market
  • Break out your walking shoes for a tour of Forest Park, Portland’s largest urban park 
  • Show your support and celebrate at Portland Pride
  • Explore multiple neighborhoods on bike during Sunday Parkways
  • Prepare yourself over multiple weekends for Portland Street Fairs, a mix of music, crafts, food, and people
  • Take a friend to a u-pick farm on Sauvie Island for fresh berries, flowers, and more
  • The World Naked Bike Ride is also a thing
  • Listen to some incredible music at the Oregon Zoo, Edgefield Concerts on the Lawn, Waterfront Blues Festival, Chamber Music Northwest, or Cathedral Park Jazz Festival
  • Visit the Portland Mercado for food trucks serving South American, Central American, and Mexican food
  • Meet some favorite authors at Portland Book Festival 
  • See thousands of swifts take flight at Chapman Elementary School
  • Experience apple harvest season at Mt. Hood
  • Get your soak on at the soaking pool at McMenamin’s Kennedy School
  • Say meow to the International Cat Show
  • Enjoy an elephant ear and the holiday spirit at ZooLights
  • See the festive lights at Peacock Lane, a family favorite
  • Witness the incredible light displays at the Winter Light Festival
  • Celebrate the Lunar New Year at Lan Su Chinese Garden
  • Visit Powell’s Books. It’s on every to-do list, because it’s pretty amazing
  • Catch a live show: music, comedy, off-Broadway — we have it all. Keep track of upcoming performances at Crystal Ballroom, Doug Fir, Revolution Hall, Arlene Schnitzer Concert Hall, Aladdin Theater, and many more. 
  • Explore Oregon Museum of Science and Industry (OMSI), which includes everything from interactive stations to a planetarium 
  • Take a leisurely strong through the Oregon Zoo, the oldest zoo west of the Mississippi River
  • Stock up your pantry with fresh fruits and veggies at a local farmer’s market

Although most other cities might not think of Portland as a dynamic sports town, passion runs deep in the Rose City. Check out:

  • Portland Trail Blazers at the Moda Center (NBA)
  • Portland Timbers & Portland Thorns at Providence Park (MLS)
  • Portland Winterhawks at the Moda Center (Hockey)
  • Hillsboro Hops at Ron Tonkin Stadium and Portland Pickles at Walker Stadium (Minor League Baseball)
Damian Lillard vs Russel Westbrook
Damian Lillard of the Portland Trail Blazers about to hit a silky 3, photo by JamesInDigital

How to Find Work in Portland

One thing we hear from candidates who have recently relocated, or are trying to relocate, is how hard it is to secure a job in Portland compared to the city where they came from. This is mostly because, in many ways, Portland is a networking town. It’s not hard to develop a great network, but if you’re only relying on the large job boards and ignoring the human element in your search, you may be missing out on some incredible opportunities. 

We recommend: 

Also, mix up your job search and try some new things. We’ve put together some great tactics, topics, and resources.

How to Weather it All

The first thing to know about Portland is that we tend to skew more casual in terms of style than many other parts of the country. To give a bit of context, it wouldn’t be out of place to see jeans and a plaid shirt at even the nicest restaurants in town. Outside of a few industries, people tend to skip on ties, suits, and heels. 

As far as weather goes, everything you’ve heard is true i.e. it rains a lot here. It’s not like rain in the Midwest or on the East Coast though — typically it’s a persistent, grey, soggy drizzle with some breaks and heavier downpours intermixed. Despite what you’ve heard, it’s not looked down upon to use an umbrella, although many people forgo serious rain gear for shorter trips. Honestly, our best advice is to wear some mostly waterproof, relatively flat shoes and layer sweaters and jackets that don’t absorb tons of water. You’d be amazed what a difference dry feet and a warm core make.

Sweet golden dog in a yellow rain jacket

On the other hand, Portland has, on average, 144 days of sunshine, almost all between the months of May and October. Like, our summers might be some of the best in the world. Styles still tend to be pretty casual, but you’ll see a lot of sunburns after the first nice weekend, so sunscreen is always in fashion. Although Portland summers are very agreeable, in the last decade we’ve seen an increase in high temperature days and wildfires, which can wreak havoc on air quality.

Some general items and styles that are always in: clogs, plaid shirts, Blazers gear, Timbers gear, reflective biking attire, Dr. Martens, Blundstones, Birkenstocks, anything Nike, Adidas or Columbia, wool sweaters, Pendleton, jeans, beanies, dogs, glasses, beards, buns, bangs, overalls, oversized jackets, tattoos, and taking your style a little too seriously.

Relocating to Portland? Here are some recommendations from our crew:

  • Abby: The Peninsula Park Rose Garden — especially in the summer!
  • Allie: ¿Por Qué No? taqueria
  • Brittney: Japanese Garden, Sailing classes on the Willamette, and Kachka for amazing Russian cuisine
  • Corbin: Blue Collar Wrestling at North Portland Eagles Lodge
  • Cory: Go to a Blazers game
  • Debbie: Dog walks at Gabriel Park in SW Portland and Maplewood Coffee & Tea 
  • Elaine: Timberline Lodge at Mt. Hood — have a cup of hot cocoa and sit by the fire
  • Elizabeth: Walk across Tilikum Crossing
  • Gwen: Celebrate Oktoberfest at Prost! or Stammtich in September
  • Hannah: Try the beet melt sandwich and Peach Carina at Ecliptic
  • Jen: Hollywood Theater (+ pie spot!); Sunday night jazz at Clyde’s; Troll Bridge
  • Jenn: Eat at Sugarpine Drive-In, which is right off the Sandy River in Troutdale! Highly recommend their ice cream selection.
  • Josi: Annie Bloom’s Books to browse and hang out with their shop cat, Molly
  • Juanita: Paulina Lake!
  • Karen: Fremont Fest in August or just walking around the Beaumont neighborhood
  • Kathleen: Get to know all the unique food, activities, and landscapes in every part of the city
  • Kati: Oaks Park for roller skating
  • KB: The Vancouver Waterfront Park + Vancouver Farmers Market (you can park and walk to both on Saturdays and Sundays during market season!)
  • Kirsten: Do a few wine tastings in Oregon Wine Country and grab lunch at Red Hills Market
  • Lauren: Food carts! Especially the ones on Southeast Hawthorne Street
  • Melissa: Portland is made for biking! Meander through charming neighborhoods, catch a yard sale, stop at a park, and keep your eyes peeled for independent shops and restaurants everywhere. 
  • Nicole: Southeast Division Street! Cibo has a great happy hour — get the spicy spaghetti
  • Pat: Feast Portland or the Portland Film Festival. Or both!
  • Rosemary: Free summer concerts at parks around town
  • Roxanne: BurnCycle
  • Ryan: Movies in the Park
  • Sally: Trip it to Manzanita, take a walk on the beach, have breakfast at Yolk, climb Neahkahnie Mountain
  • Susan: Leif Erickson Trail into Forest Park
  • Tracy: Hiking in Tryon Creek State Park
  • Wren:  Movement Portland (climbing gym), then stop by Pho Van.


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