Things to Do in Portland, Oregon

For a small city, Portland, Oregon, offers plenty of things to do. A vacation in Portland is almost always centered on outdoorsy activities. What with the Columbia River Gorge right there, Portland attracts a certain type of soft adventure travel loving tourist. Portland is also a wonderfully “green” city in more ways than one: The plentiful rain leads to lots and lots of verdant vistas, and the general ethos of the small city is quite ecologically minded, as well. Travel to Portland, Oregon also should involve lots of culinary exploration; the food trucks, coffee shops, and funky original restaurants (not national chains) are a big part of Portland’s charm.

My brother- and sister-in-law live in Portland, and on a recent visit, they were perfect hosts to my (and their) family. We ate, did a waterfall hike, and saw the sights. It was a really fun weekend! Because my sister-in-law grew up in Portland, we were more than happy to follow her lead. Here are the family favorites from our vacation in Portland.

Things to Do in Portland, Oregon

Eat at one of the great McMenamin restaurants. The McMenamin brothers take old, sometimes closed houses, schools, and pubs and refurbish them to the theme of whatever the building originally was. The result is a series of completely original pubs and restaurants throughout Portland (and branching out through other parts of the Pacific Northwest, now). McMenamins pubs and breweries are, literally, tourist attractions in themselves, and should rank on any list of things to do in Portland, Oregon. Try the Kennedy School, which was an abandoned schoolhouse, now a hotel, restaurant, brewery, even a movie theater. Guests of the hotel will enjoy seeing how old classrooms have been converted into sleeping quarters, and the Courtyard Restaurant serves pub fare in what was once the school cafeteria. Another one of the McMenamin restaurants my family loved was Edgefield. It was originally a poorhouse (circa 1911), and is now a 74-acre property with guest rooms and hostel lodging, plus a pub, the Black Rabbit restaurant, Ruby’s Spa, and an on-site, working glass-blower and potter. The glass-blower sells his wares: There’s something really wonderful about seeing the vase you may buy be created in front of your eyes. My kids were fascinated.

Stay at Hotel Monaco Portland, a Kimpton hotel. We stayed here, and it was really a fun hotel. It fits Oregon perfectly, in that it’s slightly funky (wildly different wall colors, like purple and maroon, and comfortable, sometimes oversize furniture), very friendly, comfortable, and above all, green. Hotel Monaco Portland received the “silver tier” Green Seal certification for its commitment to environmental responsibility, and was one of two Portland Oregon hotels to receive the City of Portland’s “Recycle at Work” certification. It’s a luxury hotel — especially by the casual standards of Portland — and exceptionally dog-friendly. Portland, Oregon has to be one of the most dog-friendly cities I’ve seen, and this hotel holds true to this credo with an open-heartedness to dogs that’s really refreshing. Outside of staying at a McMenamin-renovated building for a vacation in Portland, the Kimpton hotels (another being Hotel Vintage Plaza) are highly recommended for the full Portland travel experience.

Hike to waterfalls around the Columbia River Gorge. Our family hikes were not difficult, though there are some challenging alternatives. I recommend the Multnomah Falls Trailhead as a great place to start. The Benson Bridge is super-easy to get to (more of an uphill stroll than a hike), as evidenced by the piles of other tourists and daytrippers. Hardy hikers can get all the way up to the top of Multnomah Falls, but families traveling in Portland with younger children should consider staying on the easy path. We hiked part of the Ak-Wanee Trail with our tween daughter; this trail starts flat and dry, but gets more rugged as it progresses. It is a 1978 branch of the Larch Mountain Trail, which is an older trail in the area, circa 1915. We also hiked around Wahkeena Falls trail, which is around 3 miles from the Larch Mountain Trail. Wahkeena Falls makes for another gorgeous but accessible waterfall hike. Unlike Multomah, it’s several smaller waterfalls instead of a single, grand waterfall.  The cascades are a very popular destination, though, and shouldn’t be missed. The highlight for my younger kid on this hike was grossing out her dad and uncle; she found a slimy banana slug (certainly not a rarity), and held it for a while. Hello, Purell!

Spend an afternoon at the Oregon Museum of Science and Industry (OMSI). This is one of the best museums of its kind that I’ve seen. My children loved it; we could have spent all day there. There are plenty of interactive stations for children to experience; the hands-on learning here is as fun as it is educational. My younger kid is excited about robotics, and using the robotic arm to play a giant game of Connect Four kept her happily busy for a really long time. There’s a Portland Children’s Museum, too, but OMSI fit the bill so perfectly that we saw no need to go to the other museum. It’s not just for kids — OMSI After Dark has science fun for adults — but the planetarium, exhibit halls, and submarine are perfect for all ages. The submarine, by the way, is a real, decommissioned sub. The tour lets guests understand how submarines work, look through the periscope, push a few buttons (not all of them!) and get a real sense of what it’s like living in such close quarters.

Have a cup of coffee at a Stumptown Coffee Roasters. A much smaller coffee chain than most hailing from the Pacific Northwest –  yes, I’m looking at you, Seattle’s Best Coffee and Starbucks –  Stumptown gets its name from one of Portland’s many nicknames. (Originally a logging town, at one point Portland was so bereft of live trees in some areas that it begat this unusual nickname.) While the bagel was only average, the relaxed ambiance and fantastic coffee makes the Oregon roasters well worth a detour from Starbucks. The cappuccino was as good as that of any upscale restaurant.

Order a waffle at the Waffle Window. Yes, that’s right, Waffle Window. It’s a hilariously cute set-up, wherein people line up, place their orders at a drive-through style window — but on foot — and then take their waffles over to the adjacent picnic benches and dive right in.  There’s a small area reserved for indoor dining; this being Portland, rain is not exactly out of the question. The waffles are just fantastic, with generous and creative toppings. If you don’t want to fall off the nutrition bandwagon too far, try the granola and fruit waffle. On the other hand, you only live once, and this is a vacation weekend we’re talking about — why not go for the berry cheesecake waffle? At least you probably won’t be hungry again before nightfall.

We were too full from all the waffles to make room for anything from one of the food trucks in Portland. They’re pretty famous, though, and I’d be remiss not to mention them. At least now my family knows that’s another thing to do in Portland…and a great excuse for a return visit.

Thank you to the Hotel Monaco Portland for providing lodging for my family.