I’ve worked in downtown Portland for years, and I often get asked about recommendations for a night out. So in this week’s blog post, I’m sharing where we ate, drank, and were merry when an old college friend recently came to town.
There are so many amazing bars, restaurants, and local hot spots in Portland, and in future posts I’ll detail some of my favorites by category. But for the purposes of this post, I’m sharing our stops on a single night out in the downtown area near Pioneer Square–from happy hour drinks to late-night treats.
This post may contain affiliate links, which means I may receive a small commission, at no cost to you, if you make a purchase through a link. See my full disclosure here.
Shop this look here.
One of my favorite little bars is Barlow, who’s Jazz Age vibe appeals to my personal love for all things Gatsby. I enjoy the “Summers Ago” cocktail (pictured above) because it combines local marionberries with lemon and vodka to create a drink that’s the perfect mix of tart and sweet.
We started here for happy hour and then walked next door to Barlow’s sister restaurant The Picnic House.
Their meat and cheese boards are incredible and were such great options for sharing with our out-of-town guests.
I’m always a sucker for a great charcuterie board, and I love that theirs includes deviled eggs. When we first tried out this particular board months ago, we were a bit leery of the “edible duck fat candle” that is also included. This time around we knew what to expect, and it’s actually quite delicious to spread on the bread!
We also enjoyed the sausage trio, and each meat is sourced locally. Here in Oregon and the Pacific Northwest region, we pride ourselves on our local food!
My husband usually orders their fried chicken (shown above) and it’s soooooo good.
I’m a big fan of rosé, so we ordered the rosé flight and highly recommend it! Three of the wines are from the West Coast, and one is from France.
Shop this look here.
Our next stop was Departure, a rooftop bar on top of The Nines hotel just a few blocks from Picnic House. It’s a popular spot amongst tourists and locals, and for good reason: it has some of the best downtown views in the city.
Though definitely bring a light jacket or coat, especially in the evening. Even in the summer, it can get quite windy! (As illustrated above lol 😂)
My favorite time to go is just before sunset, which was when we arrived. We got lucky and snagged a corner table as a group was leaving. It was the perfect spot to hangout because we were on the corner of the balcony, which provided panoramic views of the Portland skyline.
Our last stop of the evening was for late night food at The Original, a “dinerant” once featured on the Food Network’s TV series Diners, Drive-Ins, and Dives. It’s located just a few blocks north of Departure on 6th and Oak.
Most of us ordered milkshakes or floats, and as you can see we definitely enjoyed them!
My friend ordered a crispy fried chicken sandwich. I had a bite, and it was excellent!
They also serve various pastries and desserts, if you’re in the mood for something sweet other than a shake or float.
One thing that was a priority when planning our route for the night was making sure everything was within walking distance of each other. From our starting point at Barlow to our final treats at The Original, the distance is only about nine blocks.
Cheers to a memorable summer evening, filled with old college stories, amazing views, and delicious food and drink! 🥂
Have you been to Portland? What’s your favorite spot for a night out?
Let me know in the comments! Thank you so much for stopping by ❤️