A Short Guide to Downtown Portland

by Tracy Kaler  |  Published November 20, 2018

‘Keep Portland Weird’ is a fitting motto for a city beloved for its quirkiness and hipster culture but admired for its welcoming spirit. Despite gentrification, Portland remains an eccentric town with fun, down-to-earth people, and it presents more delicious food than anyone could taste in a lifetime. It’s also a city famous for coffee and microbreweries, as well as world-class wines from the Willamette Valley.

A street musician plays outside Portland Saturday Market. (Photo: Tracy Kaler)

Locals say if you can handle the lack of sunshine for about nine months of the year, you’ll love Portland and never want to leave. The town is a melting pot of folks – many East Coasters and Californians – who have ventured here for a milder climate, fewer attitudes and the laid-back lifestyle. Hence, most of the Portland that was plagued by corruption, drugs and crime in the 1970s and ‘80s no longer exists, but rather, it’s now cleaner, safer, friendlier (and more expensive). Premiering in 2011, the zany hit TV show, Portlandia, put the city on the urban map as not only a destination to visit, but an attractive place to live. A Los Angeles native explained, “Portland is a city of instantly belonging no matter where you came from or your agenda. Stay a week or a lifetime, but Portland will become home fast.”

PDX, as it’s been dubbed, is divided by the Willamette River with downtown falling on the west side. Downtown is the city’s central business district, and the hub is Pioneer Courthouse Square (701 SW 6th Ave), the town’s “living room” where you can grab a coffee or snack, hop the MAX Light Rail, chill out on the famed steps, and often listen to live music. But downtown is also the cultural heart of Portland, housing Arlene Schnitzer Concert Hall, the Oregon Historical Society and the Portland Art Museum, which happens to be the oldest museum on the West Coast. You could dedicate several days to exploring these institutions, well worth the time, but to grasp the essence of Portland – a city that has continued to reinvent itself – walk and talk to the people.

Pioneer Courthouse Square is considered Portland’s living room. (Photo: Tracy Kaler)

While out and about, pay close attention to the array of public art – easy to miss if you don’t know where to look. Sculpture, street art, metalwork and other forms – both permanent and temporary – adorn the streetscapes, buildings, plazas, and transit. Download the app, “Public Art PDX” for exact locations. Embark on a self-guided walking tour and scout out hundreds of artworks during your exploration of downtown.

On your journey, stroll east; once you reach the Willamette River, you’ll notice Portland’s parade of statuesque bridges. By far one of the most striking is the Hawthorne Bridge – a steel truss structure and the oldest vertical-lift bridge in the US. See this overpass in all its glory from the Tom McCall Waterfront Park (98 SW Naito Pkwy). A 36-acre space named after a former Oregon governor, it’s a pretty place for walking, jogging, biking or catching a breath while enjoying the water (and bridge) views. Don’t miss Salmon Street Springs, a fountain set north of the Hawthorne Bridge in the park’s plaza. In the summertime, watch little kids romp through the spritzing water or take a dip yourself. It’s PDX, so let your hair down.

The statuesque Hawthorne Bridge as seen from Tom McCall Waterfront Park. (Photo: Tracy Kaler)

From jewelry to coffee to home furnishings and craft beer, locally made products are the lifeblood of Portland and essential elements of the town’s subcultures. Visitors can immerse themselves in this creative community when they wander through the Portland Saturday Market (2 SW Naito Pkwy), an outdoor emporium founded in 1973 by artists for artists. Held every Saturday and Sunday from March through Christmas Eve in the Old Town/Chinatown neighborhood, the arts, crafts and food marketplace hosts more than 250 booths, highlighting the work of over 350 artisans from the Pacific Northwest. Browse the stalls, listen to the music – ranging from World Jazz to Haleakala – or kick back, observe and mingle with Portlandians.

Portlandians flock to the Saturday Market, held every weekend from March through Christmas Eve. (Photo: Tracy Kaler)

Don’t let the seediness of Old Town/Chinatown stop you from meandering the neighborhood and getting a glimpse of Old Portland. The gem of this district is Lan Su Chinese Garden (239 NW Everett St), a beautifully landscaped plot modeled after the gardens of Suzhou. Lan Su features an elegant collection of plants and flowers native to China, as well as a charming tea house and gift shop. Stroll the paths, bask in the serenity and take advantage of the many photo ops of bridges, walkways and pavilions.

Lan Su Chinese Garden is a gem in Portland’s Old Town/Chinatown neighborhood. (Photo: Tracy Kaler)


Situated steps from Tom McCall Waterfront Park, The Porter (1355 SW 2nd Ave), a Hilton Curio Collection hotel, provides upscale accommodations and pays tribute to all things Portland. Hospitable staff, several on-site eateries (don’t miss Chiosco Pizza Window for a grab-and-go slice) and a stylish rooftop bar with panoramic city views give guests good reasons to stay in this sleepy section of downtown that’s within a 15-minute walk to most of the area’s attractions.

Featuring upscale accommodations, The Porter is about a 15-minute walk from most of downtown’s attractions. (Photo: Tracy Kaler)

Kimpton Hotel Monaco (506 SW Washington St) occupies a majestic old building just steps from Pioneer Square. Old World luxury abounds the moment you step inside and see the eclectic furnishings cloaked in bold colors and sumptuous fabrics. Showcasing dramatic patterns and details, guest rooms depict just as much style as the lobby. Stop into Red Star Tavern for a microbrew at happy hour, every day from 2 to 6 p.m. and after 10 p.m.

The hippest of the hip choose Ace Hotel (1022 SW Stark St) in the old Clyde Hotel building, just a block from the trendy Pearl District. Rooms range from small dorm-like quarters with shared hall baths to more spacious digs with private bathrooms and city views. The website states that the Ace has “bikes, booze, coffee and dogs,” as the hotel features handmade bicycles for taking a spin, Clyde Common (one of the city’s favorite drinking dens) and a Stumptown Coffee outpost in the lobby. Four-legged friends trotting around are par for the course since pooches are welcome.

Eat and Drink

In Pine Street Market (126 SW 2nd Ave), a food hall staged in the historic Carriage and Baggage Building, choose dishes from nine of Portland’s top chefs and purveyors. The market offers an open layout, a variety of cuisines such as burgers from Bless Your Heart, Korean-style street food from Kim Jong Smokehouse, bratwurst from Olympia Provisions Public House, and other tasty fare. Plenty of seating is available in this rustic warehouse-style food court that’s also on the National Register of Historic Places.

At Pine Street Market, feast on burgers from Bless Your Heart or Korean-style street food from Kim Jong Smokehouse. (Photo: Tracy Kaler)

Catch a caffeine buzz as you sip a cup of Portland’s famous coffee at Public Domain (603 SW Broadway), a slick space where talented (and friendly) baristas work their magic. The coffee bar is ideal for grabbing a cappuccino, latte, double shot of espresso or keeping it simple with an Americano while kicking back or catching up on emails.

When asking a Portlander where to go for the best breakfast, Mother’s Bistro & Bar (212 SW Stark St) may be the answer. Heaping portions and little elbow room go hand in hand in this tiny spot that believes the best food comes from our mother’s kitchens. Lines are long, so arrive early or expect an hour-plus wait easily. Morning must-tries include the homemade buttermilk biscuits dripping with country sausage gravy alongside two eggs any style, and the crunchy cornflake Challah French toast. Mother’s is also open for lunch and dinner, cooking up comforting plates of pierogies, meatloaf, macaroni and cheese, and other sinful dishes.

Hungry patrons wait for tables at Mother’s Bistro & Bar. (Photo: Tracy Kaler)

Leaning on the crusty side and oozing old-school charm, Dan & Louis Oyster Bar (208 SW Ankeny St) has been shucking oysters since 1907. The Old Town bar offers happy hour every day from 4 p.m. to 6 p.m. and all day on Mondays and Tuesdays. Beyond raw oysters, Dan & Louis suggests Rockefeller, fried, stew and po’ boys, as well as other shellfish options – think clams, shrimp and Mussels, not to mention mixed seafood plates and clam chowder. Pair your shellfish with a pint of Portland’s Altbier by Occidental Brewing Co. or Barley Browns Pallet Jack IPA from Northeast Oregon.

Imagine that you’ve stepped inside a Parisian bistro when you enter the moody, wood-paneled barroom at Higgins (1239 SW Broadway). James Beard Award-winner Greg Higgins launched his namesake eatery in 1994, incorporating the finest ingredients and sources from the Pacific Northwest. His menu reflects the richness of the region: plump and perfectly cooked Totten Inlet mussels, gazpacho garnished with Oregon bay shrimp, duck confit, and salmon caught off the coast. The wine and beer lists run deep – many selections hail from Oregon and Washington with Europe rounding out the choices. In addition to the tavern space, Higgins features a casual albeit windowed and white-tableclothed dining room overlooking Broadway.

At Higgins, shellfish fans must try the perfectly cooked Totten Inlet mussels . (Photo: Tracy Kaler)


Book lovers shouldn’t miss Powell’s City of Books (1005 W Burnside St). The block-wide store with more than 3,500 sections lies on the edge of downtown and the Pearl District, holding the title as the largest independent new and used bookstore in the world. Its legacy began in Chicago in 1970, but Powell’s has undoubtedly become Portland’s book megastore, with the flagship opening in 1971 and the brand expanding to include five shops in the Portland area. Bookworms can join hundreds of readers and writers as they lose themselves for an hour (or a day) at this epicenter of titles in all styles and genres.

Bookworms can join hundreds of readers and writers at Powell’s City of Books. (Photo: Tracy Kaler)

When it comes to style, Portland may be more casual than other big cities, but the dressed-down look is well executed here. It’s boutiques like Frances May (1003 SW Washington St) that have Portland’s relaxed aesthetic down to a science. Outfitting both men and women, the shop stocks rare pieces from established and up-and-coming designers. Browse prairie dresses, tees, track pants, blazers and more from fashion houses like Acne Studios, HI LO, Our Legacy and Ulla Johnson.

If you can’t make it to the Willamette Valley (a region known for world-class pinot noir and an hour’s drive from Portland), pop into at Oregon Wines on Broadway (515 SW Broadway), a bottle and tasting shop where you can sample before you buy. The store-cum-wine bar stocks mostly Oregon pinot as well as a solid selection of whites, French rosés and champagne, plus several full-bodied reds from Eastern Washington. Taste one wine for $3 and if you’re shopping for several bottles, opt for a flight of three for $10 and up.

For handmade wares by local artists, peruse Artistic Portland (318 SW Taylor St), a gallery and cooperative staffed by the makers themselves. Selling pottery, paintings, candles, furnishings, jewelry and other unique items at various price points, the shop strives to celebrate the artistry and diversity of Portland. Surprise a friend or loved one with an unusual find or kitschy souvenir, made in Portland.

Shop local at Artistic Portland, a cooperative selling handmade wares by Portland artists. (Photo: Tracy Kaler)