Unwrap Portland for the Holidays

The Rose City has holiday charms for any agenda

written by James Sinks

Oh, the rumors outside are frightful. But the Rose City? Actually, pretty delightful.

If you’re among those who’ve been avoiding Portland of late, there’s no better time to get reacquainted than during the happy hubbub of the holidays. Business windows twinkle, lit-up Christmas ships bob in the river, Nutcracker ballerinas twirl and a festive tree shines over Pioneer Courthouse Square.

As you wander the famously walkable cityscape, you may wonder where exactly is the hells-cape that people keep warning about. With apologies to Mark Twain, reports of Portland’s demise have been wildly exaggerated.

Yes, the pandemic and aftermath were tough in spots, as some businesses moved out, people without homes moved in and litter spread. Now, thanks to an all-hands campaign by civic, business and nonprofit leaders, streets are cleaned daily, tourist foot traffic is approaching pre-pandemic levels and falcons are even chasing sidewalk-fouling crows, according to Portland Downtown Clean & Safe, a business-financed service district.

While Portland routinely wins accolades from afar, notably for its world-class food scene, local leaders are now heavily courting nearby neighbors to rediscover what they’re missing. It’s a lot.

In addition to downtown, where the skyline now includes the ritzy Ritz-Carlton tower, in scattered neighborhood districts there’s eclectic charm, art, parks and a palate-pleasing smorgasbord of food carts and restaurants.

The array of shopping options are just what the retail therapist ordered. Make things more spirited and follow the (weaving) footsteps of Portlanders Willie Smith and Joe Baessler, whose annual drunk shopping trips have become a thing of local lore. Nineteen years ago, the onetime staffers for local elected officials met for beverages at the venerable Jake’s Famous Crawfish. After Joe recalled how his midwest relatives would hit stores after hitting the bar, the two set out with a list scribbled on a cock-tail napkin.

They loved it and so did their soon-to-be wives. Joe and Willie have repeated the tipsy tradition every year since, through life’s ups and downs, through cancer diagnoses and kids, and through the evolution of downtown—which they agree is noticeably on the upswing.

Joe, now executive director of labor organization Oregon AFSCME, hands out gift bags on their shopping forays. Willie, recently retired, offers advice with a wink.

“Everything in moderation, including moderation,” he laughed.

Day 1

DOWNTOWN • HOLIDAY DINING + DRINKS • LIGHTS

At high-end Higgins restaurant, there’s a happy din in the kitchen and dining room again. It’s a reversal from this summer, when co-owner and James Beard-recognized chef Greg Higgins sent an anxious plea on social media for customers to return.

It worked. “A healthy downtown is vital to the life of our city and our state,” he wrote after the reservation book refilled.

With its location, sublime cheese and charcuterie, and big bar menu, it’s a perfect setting to fuel up, warm up and head out.

An outpost in the historical range of the Chinookan-speaking Multnomah and Clackamas peoples, Portland was named in 1845 via a best-two-of-three coin flip, after Portland, Maine. The loser? Boston.

You can see the fate-deciding “Portland Penny” among many exhibits at the Oregon Historical Society on the tree-lined South Park Blocks, which connect to the Portland State University campus, home to a year-round farmers market every Saturday.

Across the park is the Portland Art Museum, where a $111 million new courtyard and pavilion is slated to open in mid-November and unveil 100,000 square feet of new space. A three-story glass addition, named after a late Portland painter, Mark Rothko, connects the museum’s two major buildings.

Finish your list at swanky Swine Moonshine & Whiskey Bar, and start your shopping the old-fashioned way. Nearby options range from Nordstrom and the Pioneer Place Mall to century-old menswear merchant John Helmer Haberdasher, the flagship Columbia Sportswear store and The Marie-Marie, a perfumery named after a queen and a dog.

Not open yet but already creating a buzz is the long-discussed and under-construction James Beard Public Market, which will bring food and other vendors together when it debuts in early 2026.

Don’t forget to snap selfies under the holiday tree in Pioneer Courthouse Square, affectionately known as Portland’s living room.

Portland’s living room, or Pioneer Courthouse Square, is primed for the season. (*photo: Justin Katigbak/Travel Portland*)

Now, the living room also has a fish tank. Well, with fun fake fish, anyway. A block away, acclaimed painter Mark Bennett’s Portland Aquarium teems with whimsical oceanic dioramas. While there are no live animals, there are black lights and laughs.

For smiles involving actual water, check where the Christmas ships will be afloat. Started with a single sailboat in 1954, it’s now a nonprofit-run event with more than seventy-five lighted recreational boats in two separate fleets. If they’re cruising past Hayden Island on the Columbia, grab dinner at dockside Pal’s and hang with your pals by the fire pits.

Another illuminated option is ZooLights, a dazzling wonder-land at the Oregon Zoo complete with train rides and snacks. Make reservations and expect crowds on weekends, but don’t expect many real animals. Most are sleeping, and the reindeer had better be practicing their flying.

A beautifully lit Christmas tree and colorful holiday lights illuminate a nighttime scene in Oregon, celebrating holiday traditions with families enjoying festive decorations and seasonal activities. — The Oregon Zoo explodes with ZooLights while its inhabitants mostly hibernate. (photo: Jamie Francis/Travel Portland)

Fix any post-zoo shivers with a fiery downtown tradition at Huber’s Cafe, a stained-glass-decorated mainstay since 1879. The bar staff rolls magic carts to your table to concoct flambéed Spanish coffees. Sadly, they won’t roll you home afterward.

Day 2

DONUTS • FRENCH FARE • VINTAGE SHOPPING

Do you have holiday tunes on your playlist? Serenade new sweaty friends on the 2.6-mile loop from Tom McCall Water-front Park across the Willamette River. With bridge crossings and floating sidewalks, it’s one of the state’s signature running and walking routes.

Christmas ships light up the Willamette River. (photo: Travel Portland)

When you’re done, donuts will be nearby—joy to the world.

Portland elbowed its way into donut royalty when campy Voodoo Donuts first burst onto the scene in 2003, and you can grab bacon maple bars at three bubblegum-pink-paint-splashed locations. But there’s no shortage of delicious options, from brioche at Blue Star Donuts to vegan at Doe Donuts + Ice Cream.

Since 1974, Portland Saturday Market has assembled artisans and their wares under the Burnside Bridge and nearby. It’s the largest continually operating open-air craft market in the country, and a poem to local workmanship. Indoors on certain weekends, you also can support local makers at the Portland Bazaar and the warehouse-housed Portland Night Market (also open during the day).

Colorful hanging teapots and cups at Oregon craft fair. — Portland’s Saturday Market is prime shopping during the holidays. (photo: Travel Portland)

Before the new Ritz Carlton was built, the city block housed dozens of food carts. Recalling that urban buffet, a food court at street level called The Flock PDX includes eight vendors—among them Mexican, Thai and Chinese. Unlike the old days, there’s indoor seating and beer.

Between downtown and Mount Tabor, a volcanic cinder cone with trails to views, sit the charming Hawthorne and Belmont districts. Lose hours and dollars among vintage shops, comic and music dealers, a movie theater-turned-arcade and bountiful caffeinating options. (Not surprisingly, Portland was recently named the country’s best coffee city by WalletHub.) If you have pagans on your holiday list, Moon-shadow Emporium caters to those who like Halloween better than Christmas.

For magic in a mesmerizing and neon way, bounce into immersive digital art at Hopscotch, which got its start in Texas. There’s a bar and a glowing ball pit. What could go wrong?

On Division Street, it’s a labor of culinary love at L’Echelle. Opened after one of the visionaries passed away, the place feels like a candle-decorated country cottage and invites you to savor life while we have it, with inventive cocktails and French fare including niçoise salad and delicious carrots (yes, really).

Over dinner, do a little sleuthing. In 2010, artist Chris Willis started putting his growing collection of plastic, lit-up “blow mold” Santas in December in random locations. Dubbed the “Santa Clones,” he now has 450 of them, and after setup he puts hints on Instagram at @chriswillis. The clues aren’t obscure, he said, as the goal is for people to find the free display.

“They’ve become a part of the city’s holiday events,” Willis said. There’s even a local Santa Clone-inspired beer. “I suppose it’s become my tradition, too. Their glow still makes me think of the holidays at my grandma’s house.”

For the happy glow of winning (hopefully), check to see if the NBA’s Trail Blazers—with new energy, new owners and returning, but presently injured, superstar Damian Lillard—are in town.

No matter what happens, celebrate afterward at downtown’s Black Cat Frozen Custard, where the dairy deliciousness includes affogatos, and there’s a coffee speakeasy through a wardrobe.

Your morning caroling tune-up will come in handy at Hallway PDX, an 11-foot-wide karaoke bar in Old Town that’s decorated like the spooky corridor from The Shining, partly filmed at Timberline Lodge. Cocktails might explain it, but Jingle Bells never sounded so good.

Day 3

TRAILS • ALBERTA ARTS DISTRICT • THE NUTCRACKER

One of the country’s largest urban preserves and dedicated in 1948, sprawling Forest Park on the city’s northwest edge touts a basketweave of 80 miles of greenery-lined trails. The paved ones are better on early damp mornings.

Once your appetite awakens, your inner hungry hippie will feel happy and healthy at Off the Griddle, started as a food cart and now a vegetarian breakfast hot spot with one of its two locations in the Alberta Arts District. Choose from waffles many ways, and don’t miss the surprising not-really-sausage.

Explore Northeast Alberta Street afterward, where in addition to small businesses you’ll find murals, street art and signs honoring the heritage of the Portland Black community, which grew in the area in the years following World War II.

Built in 1914 overlooking downtown, Pittock Mansion was briefly home to an early Oregonian publisher and real estate investor who’d come west as a teen on the Oregon Trail. Now nonprofit-run, it’s open for tours and decked out for the holidays.

Elegant historic mansion with red tile roof and landscaped gardens, highlighting Oregon's architectural heritage. Featured in 1859 Oregon Magazine, emphasizing local history, architecture, and scenic beauty. Perfect for exploring Oregon's cultural landmarks and historic estates. — The distinguished Pittock Mansion is open for tours during the holidays. (photo: Justin Katigbak/Travel Portland)

Retreat from the bustle to airy and award-winning Amaterra Winery, which is tucked in the nearby west hills yet feels as though you’ve escaped to wine country. Along with valley views, seasonal menus and smooth pinots, the winery offers holiday tea on Sundays come December.

With luck, you’ll be done in time to catch the 2 p.m. matinee of Tchaikovsky’s The Nutcracker, presented by the Oregon Ballet Theatre. Sugarplum fairies and the rest of the candy-addled dream troupe come to life at the Keller Auditorium.

Ballet dancers performing on stage during a night-themed production, emphasizing Oregon’s vibrant arts and cultural scene featured in 1859 Oregon Magazine. — A performance of *The Nutcracker* by the Oregon Ballet Theatre. (photo: James McGrew/Oregon Ballet Theater)

Any remaining items on your list? Get lost in the flagship Powell’s City of Books, the largest new and used bookstore in the world, with books and gifts and great Oregon magazines in a building that covers a full block. From there, it’s a quick trip to the Northwest 23rd Avenue district, with boutiques and the first location of Portland’s inventive Salt & Straw ice cream parlor, where a pre-dinner scoop is completely understandable.

If you made reservations long ago, immerse in the regional cuisines of Thailand at Langbaan, a 2024 James Beard Award winner as one of the exquisite foodie experiences in the country.

If not, with two fireplaces plus steak, seafood and macaroni and cheese, the Fireside is another fine option among many along the popular streetscape.

For a weekend finale, join the pilgrimage to The Grotto, formally the National Sanctuary of our Sorrowful Mother. Constructed in 1924, the 62-acre property in Northeast Portland includes a cave with an altar. During the holidays, the grounds shimmer with lights, and local choirs perform inside the adjacent Catholic chapel, known for cathedral-like acoustics.

A person wearing traditional Oregon attire with a wide-brim hat observes a rocky landscape, highlighting Oregon's cultural heritage and natural beauty, perfect for Oregon-focused travel and lifestyle content. — The Grotto in Northeast Portland provides a space for reflection. (photo: Travel Portland)

It’s a chance to relax, listen and reflect on the meaning of the season, whatever that is to you. And Portland, like reconnecting with an old friend, is happy to help.