Skip to main content
This story is published in cooperation with Willamette Week and Travel Portland.
Listen up. I am devoutly pro-Portland (for better, or for worse). So when I say I love Portland, I genuinely mean it—but maintaining that love requires tender acceptance, a vivid imagination, and the willingness to explore a familiar place in new ways. My secret to fostering a genuine connection with the city is actually simple. I take “staycations”, where I map out full weekends of new activities as if I were vacationing in a new city.
And, to really get into vacation mode, you can stay overnight at a hotel! Right now, snagging a room in Portland’s central city is cheap—making it the perfect excuse to pack up the overnight bag, get some Grade-A air conditioning, and spend the weekend in the city.
So I’m offering you, dear readers, a few suggested ways to “staycation” in Portland. I hope you try at least one of them, and that they make you shamelessly proclaim your love for Portland, too.
Discover a New Portland
For those of you who haven’t set foot downtown, or in its neighboring districts in a year or more, you’d be delighted to discover a plethora of new businesses bringing life back to the area. So much so, that the first staycation itinerary is comprised entirely of shopping, eating and drinking at new locally-owned establishments downtown.
Start your afternoon with some shopping at Landdd (opened August of 2022). This culturally inspired design shop/studio and event space offers unique seasonal textiles, objects and campaigns. After Landdd, pay a visit to Hi Books. Opened in the fall of 2022, this bookstore/art gallery specializes in rare and contemporary photobooks and offers a curated collection of new, used, and decommissioned ephemera.
Even with a photobook and rug in hand, you’ll still have plenty of arm space (and daylight, since it is summer after all) to browse hand-crafted home goods at Amity Artisan Goods. Formerly a concept/popup, the brand gained its storefront in 2021 and markets art made by women, immigrants, LGBTQ, BIPOC, Latinx, and AAPI makers.
All that shopping will have worked up an appetite—try a refreshing sushi dinner at the newly opened Azikawa Japanese Bistro. Conclude your decadent day of exploring with a hotel stay in the downtown area. The next morning, wake up and hit brunch at Screen Door in the Pearl before the lines hit (ok this isn’t new, but it is new to the Pearl.) As a hollandaise enthusiast, I’m partial to the local asparagus benedict.
Give a Local Event Coachella Treatment
Finally, events are back in a big way—this summer in particular. If you’re already planning to hit up Portland’s Pride Parade on July 21, or the resurrected Project Pabst music festival from July 27-28 (Billy Idol will be there btw), go the extra step to make it a staycation.
Skip the traffic and driving, indulge in as many beverages as you please, and keep the party going for as long as you’d like before heading to the fresh sheets just minutes away from the crowds. Several hotel options within walking distance will keep you close to a lot of the multi-day summer event action! Wasabicon is on July 27-28; it’s another ideal opportunity to make the most of a weekend full of anime, cosplaying, and gaming by grabbing a room for the night.
If Wasabicon, Pride, or Project Pabst aren’t really your vibe, head to the Pearl District Beer & Arts Festival, happening from July 27-28. After a day of beer-fueled festivities, head to one of the many hotels in the area to lay your weary head on plush pillows.
Weekend on the Willamette
As temperatures heat up in the city, spending a weekend on the water is by far the easiest way to cool down. And Portland offers so much to do on the Willamette River. Why not dedicate an entire weekend to hours of lounging on the river bank, under a sunshade, slathered in sunscreen? Plus, if you treat yourself to a hotel room for the evening, you can river to your heart’s content with the reassurance that there’s a clean shower nearby.
If you’re less interested in hanging on the river bank, you can always get an early morning SUP rental. Next Adventure Paddle Sports Center is conveniently located in the Central Eastside, so you can snag one without leaving the city, before heading out to get on the water at Tom McCall Bowl Beach or Poet’s Beach.
Maybe paddle-boarding isn’t your thing but you still want to get on the river; so, rent a pontoon boat. An evening boat ride via SK Watercraft rentals—alone or with your best friend—is something you may not know you need, but I’m here to tell you that you do. Make sure to bring some snacks and beverages to keep you cool while you cruise the river!
Bike Around Portland
Explore the city by bike, exhaust yourself, and then luxuriate in a hotel. Portland is a city for bikers and if you have not taken your two-wheeler into the city’s core then now is the time. Fortunately, many centrally located hotel options offer ample bike parking for your trusty stead.
Strap on your helmet and head to traverse the Classic Waterfront Loop Ride (follow this map), a route that is 10.6 miles of mostly flat, paved bike roads. If you’re looking for a ride away from the waterfront, there’s the Summer of Pride 2023 Bike Tour: Central Loop (map here).
Make a real day of it by popping into the plant stores, restaurants and bars featured on last year’s map. Both routes are centrally located, but you can also check out PBOT’s map of bike lanes/and highways for independent exploring.