A Weekend in Portland

By Casey Martin

As a Portlander for about 10 years now, I’ve come to called this beautiful Pacific Northwest city home, and I’m not leaving anytime soon. Portland is one of those hidden treasures. You’ll hear the majority of the tourists that come through here say, “how did we not know about this place sooner!?” It’s a place that keeps an open mind towards pretty much everything, won’t judge you for what color your hair is or how hipster your outfit is and has become a foodie capital in the US. Portland is also a place that has the city atmosphere if you’re craving shopping, amazing restaurants and chic hotels, but it’s also easy to get out to explore the beautiful Oregon countryside with coast, mountain or forest all within an hour of downtown. I fell in love with Portland long before it became the chic escape it is now, but even as our tourism grows and the city becomes more well known among travelers, here’s the perfect weekend itinerary to see the best of the city!

A Weekend in Portland


Arrive at PDX on a Friday afternoon and head downtown on the MAX (the local nickname for our light rail system that runs all over the city). Tickets are cheap (about $2.50 for a one way ride from the airport to downtown) and it’s clean and quick. It will take you about 45 minutes to make your way to the city center, then jump off near Pioneer Square and head to your hotel.

I would suggest staying at The Sentinel (for an update on a historical Portland spot), The Heathman (true old Portland) or The Nines (the chic/hip spot downtown). Once you’ve dropped your bags off and checked in, head out and take in the main downtown area as the evening falls.

Portland is really walkable so you can pretty much get anywhere in the downtown area (which extends from West of the Willamette River and goes until the 405 bridge to the North and the West Hills to the West). Our city center is comprised of distinct neighborhoods, so take a look at a map before you go so you’re aware of them.

Focusing just on downtown (the East Side is a whole other article entirely), you’ll find the very hip area of the Pearl District in the area North of Burnside and pretty much everything in between the 405 freeway to the West and Broadway to the East.

Then there is SW, which is pretty much everything downtown, including the majority of the high rises in the city. It’s also home to Portland State University and the South Waterfront.

NW is the edgy hipster area of downtown and home to NW 23rd Street, a long strip of cute restaurants and shops. This area feels very much like a neighborhood with long leafy streets and old brick houses.

Old Town borders the Pearl and extends to the River and is home to some revived areas as well as our China Town and finally, my neighborhood of Goose Hollow which is technically SW but is the area West of the 405 freeway. Goose Hollow is home to the Timbers stadium Providence Park (our MLS team) and Washington Park including our famed International Rose Test Garden.

A Weekend in Portland

I would take Friday evening to orient yourself and grab dinner in the Pearl (about a 10 minute walk from downtown). Go casual and grab artisan pizza at Oven & Shaker. Grab the streetcar back to your hotel if you want or just take in Portland by night as the lights come on.


Start your weekend off with a walk through the PSU Farmer’s Market and take a look at our local bounty of vegetables and fresh flowers. Then meander through downtown and stop at any of many coffee shops for some artisan coffee. Then head West to Goose Hollow (you can walk or take the MAX) and explore the leafy, hilly streets of this quirky Portland neighborhood. Make your way up the hill to Washington Park and check out the International Rose Test Garden, then head down NW 23rd and cross Burnside to take in the long stretch of shops and restaurants. This area, which also encompasses NW 21st has lots to offer.

Make sure to stop for lunch at Blue Olive for some delicious Greek food on NW 21st, followed by an afternoon of wandering through shops. If you end up staying in this area for dinner, Ataula is a fantastic choice for authentic Spanish tapas. Finish off your Saturday with chocolates from Moonstruck on NW 23rd.


I would suggest spending Sunday exploring the Pearl and Old Town. Start with breakfast at Isabel and indulge in blackberry pancakes (my personal favorite) and a honey latte. After breakfast, wander around the many shops in this area. Towards the middle of the day, venture over to Old Town and check out the Waterfront Park along the River, take in the famous “Made in Oregon” sign, that now just says Portland, Oregon over the Burnside Bridge. Check out the Chinese Garden and wander through China Town.

Waterfront Park - A Weekend in Portland

For the evening, head back to the Pearl and be sure to have dinner at one of our many amazing restaurants in town. I would suggest Oba (for updated Cuban food), Andina (a Peruvian delight), Jamison (for a fabulous outdoor patio), Paragon (for classic local cuisine), or Piazza Italia (for authentic Italian). Make sure to make reservations for most of these dinner options as they fill up fast! Then follow up dinner with dessert at Cool Moon Ice Cream, and indulge in their buttermilk with marion berries, Belgian chocolate or Saigon cinnamon flavors.

A Weekend in Portland

Spend the rest of your weekend in Portland just wandering, it’s the best way to see the city! And if you want to take it in truly like a local, rent a bike and ride across the bridges to see the view of the skyline. Portland is one of those places that you’ll want to return to, a place that holds a very European-esque attitude and where our bicyclists rule the road. It’s a pretty special place and has so much to offer, so come on over and take a look at my beautiful home city!

Photo Credit : Nick Nieto

Author Bio: Casey is an avid traveler, exploring the world as much as she can every year.  She runs the travel blog True Colours, which focuses on showcasing locations all over the world as well as her background growing up as an expat kid in the Middle East and offering advice and tips for travelers today. She is passionate about exploring the world and seeing as much of it as she can.

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