A Very #PNW Holiday: Make the Most of Your Winter Visit to Portland, OR

Written by Riley Kissee

The philosophy to “Keep Portland Weird” and the city’s increased visibility in the media has made Portland a more popular destination than ever before. While many would say that you should visit this destination in the summer, the winter season in Portland will provide you with a truly unique and festive holiday experience. Here’s our list of the top things to experience while visiting Portland this season.

Luxury Accommodations


If you’re looking for the ultimate holiday hotel stay in Portland, look no further than the Hotel Monaco, which is located in the heart of the city. This Kimpton Hotel is the definition of trendy, possessing a whimsical color scheme and upscale vintage vibe. The rooms are spacious yet cozy, and the walls are outfitted in chic wallpaper that fittingly has birds on it (Portlandia fans will pick up on that reference).

What’s more, the Hotel Monaco pulls out all the stops during the holiday season with its festive decor. The centerpiece is a large, freshly cut Christmas tree adorned with ornaments in an exquisite white and silver theme.

The best time to take in this holiday display is during their daily happy hour, which features complimentary wine, cocktails, beers, a DIY hot chocolate bar, local coffee, delicious small bites, a pianist, even an artist creating caricatures that you can take home as a souvenir.

If you’re looking for even more souvenirs, the hotel offers a “Keep Christmas Weird” package that features a mini stuffed stag (reminiscent of the iconic Portland Oregon sign), local charcoal soap, socks with the old PDX carpet print (look up the carpet, it’s almost as iconic as the Portland Oregon sign), a branded Monaco flask, bottled cocktail for two and last but not least, a map of Portland’s holiday lights to guide you through the city.

Also, you don’t have to worry about leaving your four-legged friend behind this holiday season. Pets are not only welcome but highly encouraged to stay (scope out their Instagram to see some of their recent furry guests). And if you don’t have a pet of your own to bring with you, request a goldfish to be brought to your room to provide some company. What more could you ask for from a hotel experience.



Breakfast – Voodoo Donuts: While many local residents consider Voodoo Doughnuts to be overly touristy, it’s a unique experience that’s worth the wait. Known for their peculiar flavors, they have several festive offerings such as the Dirty Snowballs Doughnut (Chocolate cake doughnut with marshmallow topping, dipped in coconut and a dollop of peanut butter in the middle) and the Mexican Hot Chocolate Doughnut (Chocolate Cake doughnut dusted in cinnamon sugar and cayenne pepper)

Lunch – The Daily Café: The walls feature paintings from Portland artists, local products are employed (i.e. Portland Ketchup Company), the food is very high quality and the atmosphere is casually convivial.

Dinner – Langbaan: Enter a Thai restaurant called PaaDee and then find a bookshelf that’s actually a secret door. Go through that door and you’ll find yourself in Langbaan, heralded as one the best restaurants in the country. Seating is extremely limited and reservations are usually only available months in advance (unless you request to be put on the wait list and someone cancels a reservation… it does happen!)



Hubers Café: Known as the oldest bar in Portland, this place is a staple. Order the Spanish Coffee and be in awe of the flame-filled preparation.

Bridgeport Brewing: After Portland’s oldest bar, its makes sense to follow it up with Portland’s oldest craft brewery. Enjoy a limited release Ebenezer Ale.

Deschutes Brewery: There’s a handful of breweries, all of which are very good. Deschutes not only has great beer, they have incredible food and a quality, rustic atmosphere. Get the Jubelale and if you’re craving a true Northwest experience, order the Elk Burger with Face Rock Creamery aged cheddar, roasted shallot-thyme aioli and sweet field greens.



Pioneer Mall: Looking for a last minute gift? This upscale four blocks of shops has you covered.

Powell’s Books: It’s the largest independent new and used bookstore in the world. Seriously, you can get lost in this place.

Pearl District: Previously occupied by warehouses, the district has been converted into an upscale neighborhood chock full of galleries, restaurants, boutiques and shops.

Holiday Lights


Oregon Zoo: A million and half lights takeover the oldest North American zoo west of the Mississippi.

Christmas Tree in Pioneer Square: The tree has been a local holiday favorite and for good reason; the 75-foot tree display is absolutely breathtaking.

Christmas Ships Parade: Fifteen nights of celebration with a fleet of 60+ well-lit boats cruising along the Columbia and Willamette Rivers. This will provide you with a truly memorable holiday experience.

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