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7 Nights in Portland, OR

Portland surprised us with how much it has to offer. This little city in the Pacific Northwest packs a rather big punch. It provides abundant opportunities to connect with nature, is just a short drive to the coast, has easy access to Washington's many sites, boasts mild temperatures year round (by New York's standards), celebrates a thriving culinary scene and bursts with lots of character. Really, if it weren't for the 221 sunless days per year, super far left leaning folks who threaten to destroy the city, and the inundation of homeless people we would have placed this city at the top of our list. Ha! In all seriousness, I can totally imagine living here despite its flaws.

Although the neighborhoods we visited were very quiet, most likely due to the pandemic, we could easily imagine how bustling and lively this city normally is. There are restaurants, bars, food trucks and anything food related you could hope for at every turn. The casual, laid back vibe of the city really has something for everyone's taste and the people here make it very clear that everyone is welcome. Throughout the city there are authentic reminders to be loving and kind citizens usually through beautifully painted murals. There is a tone that is set here: be a good person.

The City of Bridges earns its name from the twelve bridges that cross the Willamette River. Each bridge has its own distinct character and some of them, like the newer Tilikum Bridge, even light up at night further beautifying the skyline. Portland has an industrial feel to it. The city itself is not a beautiful one per se but it does have a lot of charm and personality.

The weather here is unpredictable forcing us to cancel a few of our sightseeing plans. As we drove to Silver Falls State Park suddenly a thick, white, paste-like looming fog made visibility of even just one inch in front of us impossible. We were just seven minutes away from the falls (after over an hour of driving to reach them) but were forced to turn around by the blinding whiteness that surrounded us. There is also rain. A lot of it. Yet without fail, the sun comes out everyday to say her hellos even if just momentarily. Due to the weather in Portland we relaxed a lot and indulged in three full home days which we relished after so much sightseeing the week before.

I never thought I would end up in Portland and honestly I kept pinching myself while here- was I really here? Did we really drive all the way across the country to Portland? If it weren't for this road trip, I would have likely missed this city entirely. I am so happy we spent a week here to experience firsthand how special this place is.

The Pittock Mansion

Perched on a hill, this historic chateau in the West Hills of Portland offers private tours, forty-six acres of walking trails and the most incredible views of the city with Mount Hood dominating the horizon. We were really lucky to see the mountains on a clear day. Often, they are hidden by fog and clouds. What a stunning view!


Our house in Beaverton, Portland was the perfect retreat. We were nestled in nine acres of forested land allowing us to rest, recover and relax from a pretty vigorous schedule while we were in Gold Beach, OR. You can find this property on VRBO, ID# 7907348. The house is well stocked, spacious, immaculate and very comfortable. When our kids could not get a strong WiFi signal in their downstairs bedrooms the host immediately brought us an extender ensuring that they were capable to log into their school meetings during the week. Just last year I would have been petrified by the idea of sleeping in a large home in a forest. So much has changed. This city girl is slowly adapting to nature and sleeps like a baby while tucked in the woods.

Alberta Arts District

Alberta Street, in Northeast Portland, is packed with colorful murals, galleries, restaurants, bars and retail shops. I loved the vibrant vibe here even while its sidewalks were barren. With no one in site, the lively energy of the neighborhood seemed to seep through the buildings. It's just waiting, not-so-patiently, to serve the thousands of locals and tourists who frequent the area.

Every single shop in this neighborhood, 100% of them, proudly posts a BLM sign on their window- many storefronts displaying other messages for justice along with it. When we pass through communities where all members participate in this movement I wonder how many of them are just dutifully following along versus how many of them fear the repercussions of not posting what is expected of them. This is definitely the part of Portland that earns the city's far left reputation. We spoke to a couple of locals who have lived in Portland for many years and they said that the people residing in this neighborhood are the people who are destroying their city and its values. Since we were lucky enough to spend a week in the city, I saw firsthand that most of Portland is not a loud, screaming group of people who threaten to cancel you from society if you don't succumb to their ideals by proving you do through visual representations. The majority of the folks here truly are very accepting of all walks of life, and don't need you, nor themselves, to post a sign to prove it. As we travel the country, we are finding that these neighborhoods with very loud voices are actually the smallest in numbers and are not as harmful as the media portrays.

With all its political tones and quirks, I couldn't stop photographing this high-spirited neighborhood.

Salt & Straw

Salt & Straw is the most talked about ice-cream shop in Portland famous for its unique flavors (think honey lavender and olive oil ice cream). Of course, a visit here was on our agenda. I have never witnessed our children face such difficulty selecting an ice cream flavor- there truly are too many tempting ones to choose from! Finally we settled on eggnog (for me!) and three chocolate gooey brownie scoops. The flavors live up to their name, we all agreed these were some seriously unforgettable scoops.

Mississippi Avenue

Mississippi Avenue, in North Portland, is another example of a Portland neighborhood full of personality. Once one of the worst neighborhoods in the city, it has now claimed its stake as one of the trendiest. There is a hurtful history here of laws prohibiting the sale of property to blacks and Asians who were eventually displaced by gentrification. For a city that prides itself in social justice issues, I found it hard to believe that this piece of history was so quickly swept under the rug to make room for new, mostly White tenants and bars that cater to the hipsters in the area.

Like most popular neighborhoods in the city, Mississippi Avenue is lined with local shops, restaurants, bars and food truck clusters. Similarly this historic avenue lacked the locals to stream down its sidewalks. We could only imagine how hopping Portland is under normal circumstances but unfortunately it has been marred by the pandemic keeping its folks presumably either indoors or with nature.

Voodoo Doughnut

No visit to Portland is complete without a stop in this doughnut shop that has a cult following. They offer sixty of the most creative flavor combinations that are playful and simply irresistible. We made a stop in their Old Town location where Voodoo was born. This area of the city is probably the worst impacted by the homelessness crisis. So much so that my younger kids didn't want to get out of the car, even with the promise of the best doughnut they may ever have waiting for them just a few feet away. The very pink, friendly storefront eased their nerves and ultimately they couldn't resist entering the bakery to see these beauties in person.

One thing about Portland that I've noticed is that the hype never disappoints. You know how sometimes people rave about something- a food, a movie, etc...- and then you check it out and are like "eh"? Everything that is highly praised in this city lives up to the expectations. These doughnuts were everything we hoped for and more. Everyone ecstatically recommends the bacon maple bar but since three of us don't eat meat, we avoided this tip. Instead we sampled the School Daze, Marshall Mathers, Portland Cream and Sprinkle Cake. Yes, the voodoo worked, we were smitten with the sugary sweetness intertwined with the perfectly yeasted dough.

Powell's City of Books

When I learned that the world's largest independent book store is in Portland, I quickly added this stop to our itinerary. Four of us are avid readers and visiting a book store is as equally exciting to us as visiting a chocolate shop. The store takes up an entire city block and sells one million books throughout its 68,000 square feet and 3,500 sections. This is a bibliophile's fantasy land! The biggest challenge was not allowing the kids to purchase the books they eyed as they got lost strolling in the sections of the genres they like most. We took careful notes of their choices, the holidays are around the corner! I felt bad taking them to such an incredible store and not allowing them to purchase books, kind of torturous really, but our space is so limited with our suitcases exploding and they'll just have to wait until the holidays. The thing is, my kids are pretty awesome. They totally agreed that we have no space, even for books. I can't wait to surprise them.

Mill's End Park

Portland is known for its quirky and weird character, its part of the appeal here. The weirder the better. They even have a Freakybuttrue Peculiarium Museum which features all things bizarre (note: closed during Covid). Those in search of the strange can also visit Paxton Gate and pick up a jar of a cow fetus in formaldehyde (yup, this is true. We spent a solid amount of time balking at the unusual items for sale in the storefront display). Then there's Mill's End Park, the smallest park in the world measuring at two feet in diameter. I can't help but love the eccentricity of this town!


Food trucks are as ubiquitous as bridges in Portland and are woven into the culinary culture of the city. In fact, many food cart purveyors went on to open successful brick and mortar locations. Unlike Austin and New York City where mostly mobile trucks line up along street curbs to serve its hungry visitors, the trucks in Portland are clustered together in these food truck communities closed off from the main street. The pods of trucks create their own atmosphere with music, fire pits and communal seating (closed during the pandemic). We headed over to Cartopia, in Southeast Portland, and couldn't resist ordering several orders of vegetarian gravy doused poutine at Potato Champion. Delicious and spicy, I loved every bite which took me back to December of 2019 where we munched on poutine in its homeland of Canada. Once again, Cartopia was quiet, we were the only ones in site. In fact, several of the trucks were closed. It's so sad to see firsthand how some cities are completely affected by the pandemic while others seem to have avoided an economic crash entirely. Portland, second to Memphis, is one of the most visibly affected cities that we have visited during the pandemic. The governor has ordered a no dine-in restriction, allowing restaurants to only serve take out. Not seeing sidewalk patios packed with diners as we have seen in other large cities really impacts the overall feel here.

Willamette Valley

There are endless activities to enjoy outside of Portland from hikes, whitewater rafting, and skiing to beaches and vineyards. Willamette Valley, approximately an hour away, takes you to another world of grape vines, green valleys and breathtaking vineyards.

Bethel Heights

The hostess of this lovely vineyard invited us in to explore the property while kindly reminding us that she is unable to serve us a wine tasting. Under Oregon Covid restrictions the vineyards can only sell wine bottles to go. She shared with us how much the pandemic has financially impacted their sales. She also shared that this time last year her terrace was filled with visitors. My heart truly breaks for the business owners who are suffering so greatly during these times. During our travels I have become actively conscious of how our purchases are helping boost the livelihood of others. It actually feels good to spend money these days. I loved our chat with the hostess here. I tend to chat with everyone along our journey enjoying their perspectives and insight which have greatly shaped my own. The estate bottle of pinot noir was thoroughly enjoyed by our fireplace later that evening as we contemplated all that is taking place in our country and world.

Cannon Beach

Less than ninety minutes away, an entirely different landscape along the coast awaits for the city folks who yearn for the seaside. We spent a couple of afternoons exploring the beautiful towns and sites along the northern Oregon coast. See my separate post on Northern Oregon Coast for more pictures and details. Here is a little taste for now.

Columbia River Gorge

Approximately forty five minutes outside Portland a windy, scenic drive awaits all those on a waterfall chasing adventure. None of the falls listed below require any extensive hiking. In fact, besides Bridal Veil Falls they are all right off the main road. I met locals via Instagram who were extremely helpful in making great suggestions. They, like us, are from New York but said they moved to Oregon just three months after their visit here and that the Columbia River Gorge is what pulled them to this side of the country. It truly is that spectacular of an area. I can totally relate to why they fell madly in love with Oregon after a day embraced by waterfalls. There are over ninety waterfalls just on the Oregon side of the river. Ninety waterfalls?!

Vista House

At a whopping $100,000 construction fee (in 1917!) this outhouse was termed by locals as "Oregons most expensive bathroom". Over one hundred years later, the lovely structure welcomes visitors as they enter the gorge while boasting incredible views of the Columbia River. I read that this is the windiest part of the gorge but in no way did I imagine that I may face my death here or put my children in harms way. The wind was so strong and powerful that me and two of my kids were literally being blown around when wind came through. At one point my daughter was struck with panic as she held on for her dear life to the railings that guard the Vista House. We were stuck holding on for what seemed like eternity waiting for a hurricane strength wind gust to pass so we could make a run for our car where my husband and other son were waiting (they were deterred by the wind when they first attempted to leave the car). Seeing our panic and sensing that we were in danger my amazing husband came to rescue us while he too struggled to stay standing. If the drop into the river wasn't so high, maybe the experience would have been much calmer but boy did I have a moment of strongly regretting coming here.

Latourelle Falls

Bridal Veil Falls

Horsetail Falls

Multnomah Falls

There was so much more to see and explore around the Portland area. The list of activities is honestly endless. We were so comfortable in the home we rented and the overcast skies encouraged us to stay put and relax more than we planned to. Traveling here, across the country has really felt like we have crossed the world. It is easy to stay complacent and comfortable in the places we feel safest or make up many excuses to not push through the norms we have accepted in our lives. However, it is only when we leave these comfort zones that we can directly experience the many blessings our earth has granted us and to connect with people and souls who teach us new perspectives. Through physical journeys we slowly begin to embark on spiritual ones as well. There have been many times over the last hundred and thirty-seven days of our road trip when my husband and I have wanted to cancel something on our itinerary because mostly we were being lazy and just wanted to stay home. We have noted each time how happy we were that we didn't let these voices dictate our decision because we would have missed out on an incredible experience. Pushing through is difficult, in all aspects of our lives. It would have been so easy to stay home and do nothing, but how much we would have missed if we didn't dare to wander? Too much to type...