WHY SO WEIRD, PORTLAND?
You’ll find traces of the slogan everywhere — on faded stickers, on street signs, written in chalk on the sidewalk and even splashed on the side of a live music venue in Portland’s Historic District. “Keep Portland Weird.” Many might also recognize it as the city of Austin’s slogan. It was “borrowed indefinitely” from the Lone Star State in an effort to recreate the original movement of supporting small and locally owned businesses. However, Portland has proved itself as a place that thrives on individuality, marching to its own locally sourced, sustainable baseline.
  • Mills End Park

    Located at the Southwest Naito Parkway and Taylor Street intersection, Mills End Park proudly welcomes traffic on either side of its median. You won’t find any park rangers or on-site gift shops, and the only wildlife you might see has six legs.

  • Voodoo Doughnut

    On any given afternoon in Downtown Portland, you can spot someone carrying the signature bubblegum-pink box from Voodoo Doughnut. Children and those who offend easily should be cautioned, as certain doughnuts have inappropriate names and designs. The menu offers more than 60 classic and unique varieties, such as a maple-frosted doughnut topped with bacon.

  • McMenamins Kennedy School

    In 1997, brothers and business partners Brian and Mike McMenamins renovated an abandoned elementary school building into a neighborhood watering hole. The school cleverly retains much of its historic charm. Enjoy a craft cocktail in Detention Bar, order a panini in the school’s former boiler room, and catch a movie in the converted cafeteria.

Panoramic Portland Views

Portland is definitely a vacation with a view. Several stunning ones, in fact. Discover the scenic spots around town with the best vistas — and the best photo ops.

545560756
Portland Aerial Tram

All aboard the Portland Aerial Tram! Take in views of the downtown skyline from 500 feet in the air. On a clear day, the 360-degree cabin windows allow you to see all the way to Mount Hood and Mount St. Helens.

Portland-Destination Multnomah Falls
Multnomah Falls

Experience the majesty of the tallest waterfall in Oregon, Multnomah Falls, as it cascades through the (also beautiful) Columbia River Gorge. Traverse Benson Bridge to get the best views. It’s simply gorgeous.

Portland-Destination-grill
Portland City Grill

This delicious dinner comes with a view. Portland City Grill is on the 30th floor with windows galore, perfect for seeing the city while sipping a cocktail. Time your reservation for sunset — you won’t be disappointed. 

Portland-Destination-Vista-House
Vista House

Get some history with your gorge views. Built in 1918 on the summit of Crown Point, Vista House has interesting exhibits and incredible views of the Columbia River Gorge. Make sure to check the winds before you visit.

PORTLAND CITY GUIDE - ITINERARY

Day 1

Morning

Begin your day in true Portlandian fashion by walking to Pine Street Market and fueling up with pressed juice from Kure Juice Bar. After, take an energizing stroll along Tom McCall Waterfront Park. Keep your eyes peeled for Mill Ends Park, the world’s smallest city park at only 2 feet across.

Afternoon

Head over to the Pearl District, where you’ll peruse vibrant local art galleries like the Basic Space Gallery.

Evening

Stop in Powell’s Books and get lost in the endless isles — this massive store takes up an entire city block! Then make your way to Bridgeport Brewery for happy hour, then get made-from-scratch comfort food at Tilt.

Day 2

Morning

Visit the open-air Portland Saturday Market for a cold brew and browse handcrafted artisanal gifts.

Afternoon

Play in the fresh air Washington Park. You’ll find endless delights, such as the Japanese Garden, International Rose Test Garden, and Oregon Zoo.

Evening

Catch a show at The Armory, or just enjoy dinner in the beautifully renovated building.

Day 2

Morning

Visit the open-air Portland Saturday Market for a cold brew and browse handcrafted artisanal gifts.

Afternoon

Play in the fresh air Washington Park. You’ll find endless delights, such as the Japanese Garden, International Rose Test Garden, and Oregon Zoo.

Evening

Catch a show at The Armory, or just enjoy dinner in the beautifully renovated building.

Day 3

Morning

Explore the local flavor in Portland’s affluent Alphabet District. Be sure to stop at Ken’s Artisan for a decadent almond croissant.

Afternoon

Did you know Portland is tax-free? Shop along impressive rows of commercial and independently owned retail on Northwest 23rd and Northwest 21st streets. 

DISCOVER MORE OREGON RESORTS
The Internet Explorer web browser is no longer supported by Club Wyndham. Please upgrade your browser.