72 Perfect Hours in Portland

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Travel Month continues, rounding out Mountains Week over the next few days! The surrounding areas too in some cases. As with Caribbean Week last week you can expect plenty of guest posts to delight with extra coverage. I’ve loved all the guest content so far and I hope you have too!

Sometimes a vacation is luxuriously lazy, with some activities planned among the freedom of doing whatever you want each day. And sometimes vacation overlaps with a work trip as was the case when Alex and I visited Portland. Although we were there for over a week we really only had about three days, or 72 hours, to do whatever we wanted.

What follows in this post is how we spent the most perfect 72 hours in and around Portland, Oregon. First up, photos! And then below, what to do each day of your trip.


Portland has plenty of hotel options but by far our favorite is the Paramount Hotel, a modern high-rise featuring spacious rooms and suites overlooking a plaza and centrally located to destinations like the art museum and Pearl district. It’s situated on an avenue arcade with lots of greenery and spacious sidewalks and is just minutes from the many streetcar lines that transverse downtown.

We absolutely love the rooms here. We always request a corner room on a high floor; usually we end up on the 7th floor which just clears the parking garage one block over and has two extra windows for tons of natural light. You’ll find free wifi here and cute mini fridges, but my favorite room amenity has to be the bathroom’s huge jetted tub which is like having your own private in-room hot tub! It’s confirmed to be spacious enough for two. I recommend booking directly through the hotel and asking for their best rate that includes parking, which alas is not included in the standard room rate.

The hotel doesn’t offer free breakfast but does have both a restaurant and a bar that’s quite popular with locals during happy hour in our experience. Expect to pay major $$$$ at either — I’ve included one dinner at their restaurant Swank, but I would not plan on eating every meal here.

Up on the mountain, there’s no question: if you want a delightfully rustic experience, book at the Timberline Lodge. This Roosevelt-era hideaway has been lovingly restored to protect its most beautiful artifacts, like unbelievably thick tree trunk support columns and a 4-sided fireplace that extends the entire height of a 3-story lobby. Nooks with writing desks and rocking chairs await around every corner of the spacious common area which sports amazing views of Mount Hood and will keep kids and adults alike busy exploring for hours. The lodge sports an intriguing museum with ski tools of yore, videos from the 1930s and 1940s of what staying in the lodge was like back then, and pictures that wowed us of old modes of transport.

I recommend booking a room with a fireplace (which is also more likely to give you a scenic vista back down the mountain), and though it’s an expensive add-on the s’mores kit is such a treat. All profits go towards maintaining the lodge. The lodge sports plenty of ski storage, a bar and a luxury restaurant that was delicious, though decidedly lacking in greens and vegetables. A covered entry tunnel makes getting in a breeze even during blizzards like the one we arrived in.


Although downtown Portland has streetcars and taxis, this itinerary will take you outside the city so I recommend renting a car. On this trip a reliable vehicle is an absolute must, and we wanted something sturdy that would ably handle roads whether they were dry, wet, icy, snowy or in some cases not really roads at all!

At home we rely on our Jeep, and this trip was no different. For our 72 perfect hours in and around Portland Oregon, we selected a hardy Jeep Compass for our rental vehicle. The Compass features a car-like ride while still offering 4-wheel drive to navigate tough snowy roads on our way up to Timberline Lodge. We loved having a vehicle spacious enough to fit all our gear yet still offer a very comfy ride for us and two friends we met up with in-town. Never having to fear the weather or road conditions allowed us to Set our Own Direction® — there were times when we stopped to help people stuck in mud or ice slicks while our confident Compass got us where we needed to go. In a place like Portland where you never know what the weather will throw at you, make sure you rent a vehicle that won’t derail your plans! In the Compass, we always felt great.


Our 72 perfect hours will take you along rivers and up mountains. Hopefully you’ve packed your adventure hat!

Waking up on a day one might be a challenge depending on how late your flight arrived (our usual JetBlue flight arrives at midnight local time, a very challenging 3 AM east coast time!). Wake yourself up with some coffee and perhaps a small breakfast sandwich or pastry at Case Study Coffee Roasters, a local microroaster featuring plenty of seating.

Ready to explore Portland a bit? Great! It’s likely to be either rainy or cloudy in the morning this time of year with the chance of some sun increasing as the day goes along. We like to start our trips with a walk or car ride down to the Willamette River. Portland is a city split nearly in half by the river and it features bridges both old and imposing like the Hawthorne Bridge or the charmingly patinated St. John’s Bridge, both of which can be driven, biked or walked. A great morning walk could talk you across one and back across the other.

Down the river a bit is the much more modern Tilikum Crossing, which is closed to cars but open to streetcars, buses, bikes and pedestrians. Between the spans and suspension cables you get great views of both mountains and volcanoes and at night the bridge shows off impressive multicolored lights. The west side of the bridge has much more than the East side for walkers, so I recommend doing a back-and-forth across this one at a leisurely pace.

After the Tilikum Crossing, it’s time to get a higher perspective. A 10-minute walk south gets you to Portland’s Aerial Tram which is celebrating its 10th anniversary. For less than $5 you can buy a roundtrip ticket on this fun transport which travels over 3,300 linear feet at 22 mph on its way up a 500+ foot climb. The entire trip takes under 5 minutes. If you’re scared of heights like I am this is a thrilling yet safe way to see Portland from above! If that trip leaves you feeling hungry, walk towards the river after your roundtrip ride and you’ll find lots of eating options, including burgers, thai, pizza, and a cafe.

At this point it’s probably nap time, so I suggest heading back to the Paramount for a relaxing afternoon siesta or perhaps a bath in that amazing jetted tub! Once you’re well-rested, it’s time to get dressed and eat some sushi! Take a walk down into the Pearl District, perhaps stopping for a drink along the way before dinner. We liked the Blue Hour, Pearl Tavern and Quality Bar. Your dinner destination for tonight? Bamboo Sushi SW, a true treat filled with very yummy rolls and dinners.

If you crave a nightcap, stop by the Teardrop Lounge or Departure on your way home — just make sure you get plenty of rest for what lies ahead!


Rise and shine adventurers! Your day begins with the sun streaming in through the hotel windows (or if you’re like my fiance, perhaps blocked out by those thick curtains). Wipe the sleep from your eyes and grab a cuppa Joe. This time, head to Caffe Umbria at the corner of SW Broadway and SW Madison St for a morning feast for the eyes, soul and energy banks.

Once the coffee has settled in, it’s time to take off — don’t worry, you’ll be back in Portland soon! With your hiking shoes on and your rain slicker at the ready, it’s time to head out of town and into the Columbia River Gorge, taking both Interstate 84 and local roads including the Historic Columbia River Highway. Pack your Jeep Compass full with all your gear and you’ll find there’s still plenty of room for a spacious and comfortable ride. Make sure you check on road closures though — due to recent wildfires the local road is closed along several stretches. Google Maps has all the updated information.

Your first top is Wahkeena Falls, a beautiful two-tiered waterfall just off the local road. There’s a short path of steps to climb up to the bridge that spans over the waterfall, and there are many short hikes in the area too. Wahkeena Falls tends to be less crowded than the next stop, Multnomah Falls. The Lemmon’s Viewpoint trail is a great option for a short yet moderately challenging hike to stretch your legs during this long car ride.

Next up, Multnomah Falls, which is probably Oregon’s most famous for its size and scale. It’s hard to capture the entire falls in a photograph though I tried! With a bridge across one of the tiers and a lodge if you’d like to stay here for the night, this area is very popular with tourists and can be crowded. We spent plenty of time walking around, exploring the lodge and gift shop, and just taking in the beauty of a powerful mountain spill making its way down towards the Columbia River.

About 40 minutes or so later, park your Jeep Compass in Hood River, Ore along the river of the same name and grab lunch at Full Sail Brewery, home to the beers of the same name and its restaurant with incredible views of wind surfers and kite boarders taking on the challenging chop below. You can wave to Washington state if you’d like too; it’s just across the river! At this stop we picked up a few six packs for our night at the lodge.

What lodge is that you ask? The aforementioned Timberline Lodge, your home for the night! Your early afternoon arrival may mean that your room isn’t quite ready yet. Never fear though, the helpful front desk staff will take care of your bags. I recommend making an early reservation at the Cascade Dining Room for dinner. Although pricey, the meal and ambiance are well worth it.

In the meantime, this gives you plenty of time to explore all the lodge’s features! I recommend heading upstairs to the Ram’s Head Bar first for their delightful warm drinks (in the photo essay I’m taking on a Bailey’s hot chocolate with a cinnamon stick — it is of course available sans Bailey’s too for the children or non-drinkers in your party). The bar area is surrounded by writing desks, nooks, rocking chairs and all kinds of interesting historical artifacts. You’ll also get a spectacular view out the lodge windows and up towards Mount Hood, including any skiiers, snowboarders or grooming vehicles out on the slopes. Inside, you’ll be able to see the massive fireplace heating the lodge.

Once you’ve taken it all in, head downstairs to the lodge’s museum, which details the artwork and history of the lodge, including its most famous appearance! We got a real kick out of seeing the early ski and snowboards, as well as the film and photos of tourists of generations past. The Blue Ox Bar is right outside the museum for another warm landing spot and be sure to explore the mailboxes, gift shop and many artifacts that line the main floor. Plopping down in front of the fireplace is also an option, as is heading the Wy’East Day Lounge a short walk across the parking lot.

Hopefully you secured that early dinner reservation — by now your room is ready so you can get changed and then enjoy a satisfyingly meat-heavy meal. After dinner, retire to your warm lodge room, start a fire (the front desk has everything you need!) and perhaps make a few s’mores for dessert before settling into your warm, quilted bed for what’s sure to be one of the best snoozes of your life.


A big meal the night before and an early retirement to bed probably has you up early and rested, which is great, because it’s time to hit the slopes! Timberline Lodge offers complete rentals as well as lessons and passes for all your snow activity needs. With over 75% of its trails falling into the beginner and intermediate levels, Mount Hood is a spectacular mountain for all skill levels. With tons of snowpack (73 inches of base at last check) and high elevation, this is one mountain that’s able to offer skiing nearly year-round, often well into the Summer.

My favorite trails are the Mustang Sally, a long straight slope surrounded by trees; the long and scenic Kruser and the Otto Lang, which is another long and wide trail with just a few turns that leads right back to the lodge, perfectly ending your morning ski or snowboard session. Head back to your room to shower and change and get ready to go back to Portland proper.

Now it’s time to say goodbye to all the lodge’s company — checkout time! We usually check out and then head down to Mt Hood Brewing Company, located at the base of the mountain, in our Jeep for brunch.

Heading back into Portland will feel faster because this side of the trip has no stops. Once you’re back in Portland, salute your morning’s exercise with a yummy donut (or 3) from either Blue Star or Voodoo. The locals are very passionate about their donuts — apparently it’s a faux pas to not have an opinion about which place is better. Personally I find them to be more like heavy cakes than donuts at both locations but we found the selection at Blue Star more appealing to our taste buds.

Check back in at the Paramount for your final night’s stay, and then to keep your legs feeling stretched and fight the onset of soreness, head up to one of the city’s many parks for a casual walk and views of downtown. I personally like Mt. Tabor Park a lot for its mix of tall trees, easy-on-the-knees dirt paths and exceptional downtown views. For a more peaceful city escape Tanner Springs Park is a small getaway right in the heart of the city that allows easy walking access to the rest of the Pearl District. And depending on the time of year, Peninsula Park Rose Garden is one of many rose gardens in the city well worth the visit.

After you’ve tired yourself out, head back to the Paramount for a leisurely dinner at their restaurant Swank (and cap it off with a cocktail at the bar Swine right across the hall if you wish) before retiring to your room for the last of your 72 perfect hours in and around Portland, Oregon. It’s been a great trip, hasn’t it?


  1. February 6, 2018 / 12:13 pm

    This looks like such a fun trip! Those donuts look so yummy and that is interesting about the tram!


  2. Shelby
    February 6, 2018 / 12:50 pm

    I've never been to portland! it looks like a blast!


  3. February 6, 2018 / 12:58 pm

    I used to live in Portland as a teenageer and this was such a throw back. I haven’t been back in over 12 years, I think I’m long overdue!

    xo Jessica

  4. Lacey
    February 6, 2018 / 1:25 pm

    This looked so fun and beautiful!


  5. February 6, 2018 / 9:44 pm

    This spot is totally on my bucket list and now I want to go even more!!

    So fun!


    • February 20, 2018 / 9:30 am

      Awesome, glad this post further inspired the travel bug!!

  6. Klj1
    February 6, 2018 / 11:46 pm

    Ahhh❤️.. love my home?

    • February 20, 2018 / 9:30 am

      I love your home too lady!! 🙂

  7. February 6, 2018 / 11:59 pm

    Such an amazing place. I am definitely going to add it in my bucket list. Thank for sharing the information. Love the pictures!


    • February 20, 2018 / 9:30 am

      So glad you like them Rita!!

  8. February 7, 2018 / 12:41 am

    I’m dying to go to Portland. It looks like such a great place to visit!


    • February 20, 2018 / 9:29 am

      It's such a fun little city. Having friends there really helps!

  9. February 7, 2018 / 3:31 am

    This sounds like such a fun trip. Oregon is beautiful, I’m going to need to take another trip out there!


    • February 20, 2018 / 9:29 am

      Agreed, I can't wait to go back!

  10. Liz
    February 7, 2018 / 1:15 pm

    This looks like so much fun! Oregon is such a beautiful place! I need to make it up to Portland one of these days 😉


    • February 20, 2018 / 9:29 am

      It's not a place I had on my list, but my fiance went to college there and now after visiting it I can't wait to go back!

  11. hannahcstark
    February 12, 2018 / 8:45 am

    My best friend just moved to Portland! I told her I need to go visit her because she has the best pictures of the place. So do you! Looks like a fun trip:)

    xoxo, Hannah

    • February 20, 2018 / 9:28 am

      Thank you Hannah!

  12. Kristin
    February 13, 2018 / 1:23 am

    If you're a donut fan, next stop at Joe's Donuts in Sandy on your way up to or down from the mountain. They're not fancy (like Blue Star) or quirky (like Voodoo) but they're awesome! My brother has been known to drive to Sandy and back from Portland just to pick some up.

    • February 20, 2018 / 9:28 am

      Love the recommendation, thank you Kristin!!

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