The Ultimate Weekend Adventure In Portland, Oregon

A tiny house, waterfall hikes, and craft everything.

By: Alan Maxcy

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If you are anything like me you get tired of the daily grind and your immediate environment every 6-8 weeks. This is precisely why you need to have a few weekend getaways in your back pocket for your next Monday afternoon I’m-booking-a-trip-on-Expedia-right-now meltdown. Portland has everything you need for a fun and refreshing weekend away from the office. Outdoor Adventure. Check. Craft Beer. Check. Craft Coffee. Check. Craft...well, everything. Check! The perfect change-up from your Starbucks, work, take-out, Netflix routine.

Photo: Alan Maxcy

Where should you stay?

Tiny House. Need I say more? I mean you are going to Portland, you can’t just stay in the Holiday Inn by the Airport. You have to embrace the Oregon culture and think out of the box. What better way to do that than staying in a Tiny House on a tiny volcano. This little converted 2-car garage on the side of Mt. Tabor has all of the modern amenities you need (full bathroom, full bed, full kitchen) packed into a charming 400 square. foot package. It doesn't get more Portland than this.


Photo: Alan Maxcy

First things first, start your day off with an espresso from Stumptown Coffee just a few blocks from the house. After that enjoy a fresh and locally sourced breakfast from Fern Kitchen. Go ahead and treat yourself to a big hearty breakfast, you will definitely burn it off today.

After Breakfast, head to Multnomah Falls before all of the huge crowds show up. Multnomah is one of those attractions that you just have to see while you are in Portland. Is it crowded and touristy? Sure. Is it still spectacular? Absolutely. When you arrive to the falls go into the visitor center and ask a park employee for a trail map. If you tell them you would like to hike the Multnomah-Wahkeena loop, they will highlight the route for you on your map. This hike is an intermediate 5 mile, 1,500 ft elevation gain hike that features 6+ waterfalls. It gives you a beautiful snapshot of what the Pacific Northwest landscapes have to offer.

Photo: Alan Maxcy

After Multnomah you are going to want to take a load off for a little while. Drive just a few miles north to Thunder Island Brewing for a flight of craft beer and a burger. If you catch Oregon on a sunny weekend you can sit outside overlooking the Columbia River and the Bridge of The Gods.

A couple miles south of Thunder Island Brewing there is another breathtaking waterfall that is worth checking out before heading back to Portland. The Wahclella Falls hike is an easy 2 mile out-and-back hike to a stunning double waterfall.

Photo: Alan Maxcy

After Wahclella head back to your Tiny House to shower up and get ready for dinner. The Kennedy School is essentially your High School dream come true. It is a 1915 elementary school converted to a restaurant, theater, bar, soaking pool, hotel, and brewery. Yes you read that right. You could spend a whole day exploring all of the hallways and converted classrooms. Grab some grub and local beers at one of the pubs and pretend that you are back in Chemistry class.


Photo: Alan Maxcy

Start your day off with a run (or drive) to the top of Mt. Tabor. On a clear day you can see Mt. Hood in the distance. Now it’s time to fuel up on coffee and donuts. Head over to Blue Star Donuts on 23rd Ave. for a donut (or two, or four) and walk down to Barista for a latte.

After you are sufficiently caffeinated, drive down to Powell’s Books and browse around the endless shelves of new and used books. There is even a room of rare books that you can’t find anywhere else. If you purchase something your parking will be free.

Photo: Alan Maxcy

Today you would be remiss to not go west to the Pacific coast and check out Cannon Beach. On the way there travel via highway 30 towards Astoria. Astoria is a quaint little port town 25 miles north of Cannon Beach. Stop by Fort George Brewery + Public House for lunch and some more Oregon craft beer before continuing on to Cannon Beach.

Ecola State Park is next on the agenda. Ecola features a beautiful overlook of Cannon Beach and Haystack Rock as well as a 2.5 mile historical interpretive trail called Clatsop Loop Trail.

From Ecola State Park head further down the coast to Cannon beach and grab a cup of coffee and a pastry at Sea Level Bakery + Coffee. Now you are ready to go for a stroll on the beach and take in the sights.

Photo: Alan Maxcy

From there, head back east towards Portland on highway 26. In the Pearl District there is a Mexican restaurant serving up authentic, farm-to-fork eats. Verde Cocina uses seasonal, local ingredients to create some unique and healthy Mexican dishes.

Finally you can finish the night off at one of the many pubs and breweries in the Pearl District. 10 Barrel Brewing Company is open until 11pm on Sundays.

Cover photo: Alan Maxcy

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Please respect the places you find on The Outbound.

Always practice Leave No Trace ethics on your adventures. Be aware of local regulations and don't damage these amazing places for the sake of a photograph. Learn More

Please respect the places you find on The Outbound.

Always practice Leave No Trace ethics on your adventures. Be aware of local regulations and don't damage these amazing places for the sake of a photograph.