Travelogue | Weekend in Portland

Washington Park Stairs

Downtown Portland | the whinery

Spring Magnolia - Portland


Downtown Portland Signs

I love weekend getaways. I literally live off that rejuvenated feeling I get after being some place different for a few days. Luckily for me, I live a hop and a skip away from cities and towns ripe with endless exploration opportunities.
We spent a weekend in Portland last month, so I’m putting together this rough guide to having a fun weekend in Portland.

Portland is one of a few cities that I’ve always wanted to live in. Except I’ve learned this lesson that moving to a city you love is a sure-fire way to fall out of love with that city. Instead, spending a few days or weeks here and there, is what keeps the love affair going. It’s sort of like a fling that way.

The Willamette River

Powell's Books

Washington Park

Smith Tea

Dinner time at Caffe Mingo

I still think going by train is the best way to get to Portland from Vancouver if you have time. It’s an eight hour scenic and relaxing ride, but that’s me, I’ll take train travel over any other form of transportation.
We went by car this last time, which is a breezy five to seven-hour drive depending on traffic and wait at the border. Going by car has its advantages too, like breaking up the drive with a pit stop in Seattle for coffee. Singing off key for hours to your favourite songs is something you can’t do on the train or plane – so that’s a point for going by car.
Portland is amazing for leisurely getaways; it’s compact and walkable, has incredible food (and beer!), beautiful parks, trails and outdoor adventures, glorious tax-free shopping and some of the friendliest people you’ll ever meet.

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Spring in Portland


Portland Heathman Hotel

Portland Union Station

Bouquet at Heathman

After a few visits, I still go armed with a new itinerary – mostly recommendations from Portlanders and other Portland lovers – I don’t think I could ever run out of things to do.
So this is by no means a definitive guide since I feel like there’s still much to discover. This is just a little list of places I’ve traipsed and loved, and a few other recommendations I’m yet to try.
For instance, I stay at the Heathman because I’m hooked on the charming friendly service and also because there are balloons and chocolate in my room when I check in. I’d love to find a cool place on Airbnb, a colourful Victorian in Nob Hill close to Forest Park perhaps?

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Coffee Break


Northwest 23rd Avenue

Of course, I want to hike Forest Park and catch the views of downtown from Pittock Mansion. Next time, I’ll take my time to explore the Columbia River Gorge and see Multnomah Falls again, with a fully charged camera this time. I also want to spend hours on the historic Columbia River Highway stopping on all the picturesque spots I’ve read about.
On my first visit, we walked the Waterfront Park, went over bridges, meandered through pretty tree-lined streets by the river and found a little bridge overlooking Union Station, then somehow wandered into the Pearl District – I think everyone should do this on their first visit to Portland.
I want to come back one weekend this summer with my friend N just for the food cart pods.
If I do get that Airbnb, I’d want to try the PSU Farmers’ Market for produce and baked goods – I’ve heard many wonderful things about that market. See, there’s still so much to be done…
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Salt and Straw


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Portland at Night

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  • Reply Mary Cressler

    Wow. I must say, I live here in Portland, and you just created an awesome and comprehensive list of some of the must-sees in my town. And I also have to admit that as big of a foodie as I am I’ve NEVER been to Ava Genes!!! It’s #1 on my date night list, and whenever we get a sitter it’s the first place I call…. and it’s ALWAYS booked 🙁
    Though the one thing that hasn’t happened to me? I haven’t fallen out of love with it here. Moved here at the beginning of 2006 and the love affair is as strong as it was the first time I visited in ’05 and up and moved here 😉

    13 May, 2016 at 3:08 pm
    • Reply Elsa | the whinery

      Thank you Mary! See, I knew Portland was special, that love never fades:-) You have to try Ava Genes, book a month ahead if you have to, that’s what I did!

      17 May, 2016 at 9:37 am

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