Things To Do

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Alberta Arts District

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Located roughly fifteen minutes from the Ecotrust Building, the Alberta Arts District is a must-see NoPo neighborhood. Start with lunch at Radio Room, a funky, loosely 50’s themed diner at Alberta and 11th. Try the roasted brussel sprouts and bloody mary, and make sure to hit the art-o-mat (jukebox turned art gallery) on your way out. After lunch, perk up with a latte at Roseline or an espresso at Petite Provence. Now that you’re fueled up and ready to roll, head down Alberta to 27th, where you’ll find Portland’s best quartet of boutique bookstores–Parallel Worlds (Science Fiction, Horror, and everything spooky or slimy), Monograph Bookwerks (photo books, art books, and enough haute couture to last a lifetime), Vivenne (cookbooks, cookbooks, and–well–cookbooks), and Melville Books. Just up the street from this booksellers paradise you’ll also find Golden Pliers–one of Pat’s go-to PDX bike shops. Now that you’ve exited the retail timewarp to see the sun setting over the West Hills, it’s time to wind down for the night. Why not head to T.C. O’Leary’s, NoPo’s favorite Irish Pub, for a Guinness poured by Killenny Native T.C. O’Leary himself? Or, if the mood is right and the night is young, catch a show at The Alberta Rose Theatre and boogie, boogie, boogie. As they say in Grease, “But oh, Those [North Portland] Summer Nights!”

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The Pearl District & NW Portland

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Ah, the Pearl District! Fun fact: while this popular commercial district is arguably the ‘pearl’ of Rory’s venerable hometown, it’s actually named after Pearl Marie Amhara, an Ethiopian arts benefactor who spent significant time in the neighborhood (so, save that for your next Rose City trivia night). Anyway, why not start with a short walk South from the wedding venue to Powell’s City of Books? As the largest used and new bookstore in the world, this Portland staple has more than enough titles to keep you browsing for an hour (or six). Be sure not to miss the rare books room on the third floor! Now that you’ve got your 2nd edition Pride and Prejudice and Powell’s Hoodie, you might be in the market for a budget meal. Head up Burnside to NW 23rd, where you’ll find Escape from New York Pizza; conveniently located near both ballet rehearsal and volleyball practice circa 2009, this pizzeria was a childhood favorite of Rory’s. Once you’ve had your fill of pizza and pop, stop by Barista for a dirty chai or cold brew. After coffee, head up to Pittock Mansion via Lower Mcleay trail for one of the best views of Mt. Hood the city has to offer (disclaimer: with roughly 1000 ft. of vertical gain over 5 miles, the hike is fairly steep–but we think the views are worth it!).

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St. John’s

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One of Pat and Rory’s favorite Portland haunts, St. John’s is the heart of the action at the city’s Northern edge. If it's on the way, stop by The Athletic in North Portland, a favorite shop of Pat’s, for a pair of their signature PDX carpet socks (if you know, you know). Once you’ve sufficiently styled your socks, show those ankles off at Wonderwood Springs for some truly zany mini golf courtesy of Portland artist Mike Bennet. If fantasy-themed mini-golf has got you thirsty, head a few blocks down Lombard to Slim’s, arguably the best dive bar in Portland. A few other notable stops to make include Revolutions Bookshop and Final Form Records, a favorite of Pat’s for all things vinyl. Finally, head downhill for a walk along the river beneath the St. John’s Bridge–which, at the time of construction, was the largest suspension bridge East of the Mississippi (we’re not kidding about that Portland trivia, folks).

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Downtown

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If you didn’t already hit it on your walk through the Pearl, there’s no better place to start your downtown journey than Powells. While technically in the Pearl district, this independent bookstore–the world’s largest–feels like a city in and of itself. Once you’ve perused the shelves to your heart’s desire, drop in at Courier Cafe around the corner on SW Oak to grab a latte or, if you show up at the right time, some of the best shaved ice in Portland. Now that you’re caffeinated, head South along the Park Blocks to the Oregon Historical Society. Free to Oregon residents, and a pretty good deal even if you’re an out-of-towner, this museum offers a deep dive into Oregon’s history. If you’re less of a historian and more of an artist, the Portland Art Museum, directly across the street from the Oregon Historical Society, is an excellent option for your afternoon (though you’ll want to be sure to plan a return visit for November 2025, when the museum’s Rothko Pavilion will open to the public with an additional 100,000 ft. of gallery space).

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Southeast

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For those of you looking to browse small businesses, bar hop, or cavort between cafes, Southeast is the neighborhood for you. With dozens of unique neighborhoods, this quadrant has tons to offer the discerning visitor. There’s much to do, but we’ve narrowed our picks down to a few centrally located venues where the good times roll. If you’re looking to catch a movie, we recommend the Bagdad Theater on Hawthorne. This movie house, opened in 1927, is a veritable treasure trove of funky decor, classic Golden-age movie house styling, and at least 3 different bars. For arcade lovers of all ages, we recommend checking out QuarterWorld on Hawthorne. This classic arcade offers an affordable (think $5 and two hours of fun) afternoon activity, and a selection of arcade games ranging from pinball and arcade classics to the latest and greatest in arcade gaming. If you’re looking to get a sense of the natural wonders of Southeast, head over to Mt. Tabor to climb an extinct volcano; while the stairs are a doozie, the view of the city is hard to beat. If dancing is more your speed, check out The Goodfoot, located at Stark & 29th, just around the corner from award-winning Ken’s Artisan Pizza, is Portland’s premier spot to boogie down (at least, according to Sally and Graham). Check out their calendar for a full list of themed-nights, but we recommend Soul Stew on Friday nights for maximum motown goodness. With a laid-back atmosphere and welcoming vibes, you can’t go wrong with this Portland classic. Last but certainly not least, the Hawthorne Asylum offers easy access to some of the best food trucks in Portland’s bustling street food scene.

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The Gorge

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Just East of Portland, the Columbia River Gorge offers stunning vistas, beautiful waterfalls, and one extremely enigmatic sturgeon. Start your trip with a stop at Multnomah Falls; just thirty minutes East of Portland, this 600 ft. tall waterfall is a must-see on your Oregon trip. After a quick, very steep hike at the falls, stop by for a bite to eat at the historic Multnomah Falls Lodge. Continuing East on I-84, make sure to stop at the Bonneville Dam and Fish Hatchery. Visit the museum to learn about the history of the dam and see the fish ladder, and then stop by the fish hatchery to meet Herman the sturgeon. At ten ft. long and 500lbs, he’s basically a big, friendly dinosaur. After you’ve met Herman, continue East and stop by Hood River for lunch in their historic downtown, as well as some unbeatable views of Mt. Hood. If you’re not ready to call it quits on your gorge adventure, continue on to the Dalles for an afternoon stop at the Columbia River Gorge Discovery Center. Perfect for kids and adults alike, this museum combines deep geologic time with local history, and offers fantastic views of the drier half of the Columbia Gorge just East of the Cascades.

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The Coast

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Roughly 90 minutes from Portland, the North Oregon coast offers a glimpse into the wilder side of the Beaver state. Start your trip with a visit to Ecola State Park, just off Highway 26 North of Cannon Beach. This state park offers stunning views, incredible hikes through old-growth Sitka Spruce, and a familiar view for fans of the Goonies. After a visit to Ecola, head into Cannon Beach for a stop at Public Coast Brewing (Gluten-Free Friendly, as well as Luci and Charlotte Engstrom approved) and a mandatory visit to Bruce’s Candy Kitchen for saltwater taffy. To get moving in the afternoon, we recommend heading South. Drive along 101 to Oswald West State Park for a trek up Neahkanie and the best view of the coast around, or stroll down to Short Sands Beach to watch the surfers and take it easy. If you’ve got a night to spare, book a room in Astoria, roughly forty minutes from Cannon Beach and two hours from Portland, and wake up early to watch the ships coming in over the Columbia River Bar before checking out the Columbia River Maritime Museum to learn more about the ‘The Graveyard of the Pacific’. Big trees, big waves, big cliffs–the North coast has everything you need to live large on your Oregon visit.