The Best Places in Portland, Oregon

Now when I first decided to head to Portland, Oregon (and the surrounding areas) I was picturing lush green pine tree forests, hiking, hipsters, coffee shops, and hippies. I mean, the show Portlandia has to be based off of something right?! Now I was not disappointed as far as the lush green pine tree forests were concerned – I saw a great deal of this, yay! – but I also was instructed by multiple different people that while I was inside the city of Portland that I needed to try a whole list of donut and ice cream shops. Don’t get me wrong, even though I try to eat relatively healthy, desserts are my weakness and I will very rarely turn down a donut or an ice cream cone… but I was just so shocked that when I told people I was in town for 1.5 weeks, these dessert havens were at the top of A LOT of people’s recommendation lists! Who knew that Portland was the dessert capital of the Pacific Northwest!? Anyways, enough of my surprise and shock at this strange revelation (or should I say “weird” seeing as Portland’s whole tag line is “Keep Portland Weird” which btw I really didn’t find it all that weird! but I digress…) and on to the important things like what the heck should you do in Portland?!

Places to Visit

International Rose Test Garden – This is possibly the most beautiful rose garden I have ever seen and an extremely valid reason as to why Portland has been nicknamed “The City of Roses”. There are so many incredible roses in every color imaginable from all over the world! The roses bloom from May through October although I was there in peak season, which is June. I was also quite lucky with the weather during my time in Portland and had an amazingly sunny week! I spent hours walking around the rose garden with my dog, taking photos, catching up with friends and family on the phone from various benches surrounding the rose flower patches and literally stopping to smell the roses.

Powell’s Bookstore – The largest independent chain of bookstores in the world! This massive bookstore is a staple in Portland. You can browse the many many rows of books or grab a seat at the coffeeshop inside where I enjoyed an amazing iced tea and relaxed after browsing through the store for a while. Definitely stop by and grab a book!

Pioneer Courthouse Square – Also colloquially known as Portland’s Living Room is a beautiful outdoor square with steps that go up in an amphitheater style surrounding an amazing set up of flowers in semi circles. There was also a painted car on display off to the side as an art exhibit. There are adirondack chairs for lounging at the bottom of the steps or join many of the people sitting and hanging out on the steps. You can enjoy food or drinks from one of the many food carts stationed at the top of the steps. I spent a few hours here one day sitting outside on the steps with my dog just enjoying the sunshine and the people watching! You could even bring your new book from Powell’s and hang out and read! 😉

Portland Outdoor Store – Family owned and three floors of everything you might need for an outdoor adventure – including the Portland based brand Pendleton, known for their woolen blankets and clothing – this outdoor store has been around since 1919 which is incredible! The people that work there are also extremely friendly and offered my little pup a dog treat! Definitely cool to walk around this old school shop with a wide array of clothing, accessories, and entire sections with cowboy boots and cowboy hats!

Martha’s at Revolution Hall – This rooftop bar is crazy cool because it is on the roof of what used to be a school! With ample seating, great views of the city, and awesome ciders (I don’t really drink beer) it is the perfect place to hang on a sunny day with friends! This is where I spent my first afternoon in Portland and it was the perfect welcome to the city! I caught up with the ladies, sipping drinks and taking in the views!

Laurelhurst Movie Theater – If you’re as much of a movie theater lover as I am, definitely go see a movie at the Laurelhurst. With an awesome light up sign out front, the interior matches with a chill hipster, old school vibe. You can order the typical movie theater favorites like popcorn but if you didn’t have time for dinner before, you can grab a slice of pizza at the food counter as well! You know I had both pizza and popcorn… 🙂



Blue Star Donuts – Blue Star was my absolute favorite donut place in Portland. So much so that I actually went twice to check out two different locations! They have extremely interesting & trendy flavors – “Blueberry Bourbon Basil” and “Mexican Hot Chocolate” to name a few. But my favorite was “The O.G. (Orxata Glaze)”. They also offered vegan options! The shops aesthetic is clean, white and trendy complete with a neon wall sign for a perfect #instaworthy pic. It was also nice that while you stood in line waiting, all of the donut options were displayed in the glass case as you walked by so you could decide while you waited (although both times I went, the line was quite short).

Voodoo Donuts – The donuts at Voodoo were also quite good and included options such as “Oh Captain, My Captain” complete with captain crunch cereal layered on top or similar options with oreo cookies on top, fruit loops, cocoa puffs etc. as well as other Bavarian cream filled donut options. They also offered vegan options! The aesthetic of this shop is much more old school with a lot of bright purple and wacky voodoo type paraphernalia making it seem a bit crowded. A plus though was the circular glass case featuring a spinning display of all of the different donut options so you could look in and point to a donut that seemed tasty to you!

Donut Days – The mini donuts sold at the cart outside of the rose garden were absolutely delectable and the perfect afternoon snack once I finished perusing the garden. You could buy either 6 or 12 and the man who owned the cart was working it and offers to drizzle toppings on them for you! Paired with a La Croix I was happy as could be sitting at one of the outdoor tables in the shade with my dog as I casually polished off all 12 mini donuts.

Ice Cream

Salt & Straw – This trendy ice cream shop which is based in Portland is so amazing that it has expanded throughout the west coast! They serve incredible and interesting flavors such as “Cloudforest Chocolate Hazelnut Cookies & Cream” and “Honey Lavender”. What’s more, is that they are famous for letting you try as many samples as you like! It is amazing for an indecisive person like myself who wants to try every flavor before picking and is especially helpful when they have crazy flavors like “Pear & Blue Cheese” and you can’t fathom how that might taste as an ice cream flavor. As if it wasn’t exciting enough already, every month they have a different theme featuring new flavors only available for that month. When I was there in June it was a collab with local Portland based brand Pendleton and it was the campfire series featuring flavors like “Spruce Tips and Huckleberry Crisp” and “Berries, Beans & BBQ Sauce”. You can check their website any given month to see what the feature of the month is! They have amazing waffle cones that they make fresh on site too so if you’re a cone person like I am, definitely try it!

Wiz Bang Bar – This cute little soft serve ice cream bar inside of the Pine Street Market is owned by Salt & Straw and serves the best soft serve I have ever had in my life – I went twice. They have 6 flavor options to choose from and again, they let you taste all of them before selecting! My peronal fav was the “old fashioned donuts” flavor (as if I hadn’t had enough donuts for the week) but it really was indescribably delicious! For the classic fans out there, they had vanilla custard and chocolate fudge and for your more adventurous flavor tasters a strawberry coconut! They also have a special flavor of the month so when I was there it was matcha blood orange but this changes constantly. You can go for just the soft serve – the ice cream is flavorful enough you don’t actually need any toppings – but I figured why the heck not and added some cookie dough bites on top of mine!


Proud Mary Coffee – Amazing brunch spot in a cute neighborhood. The waitress was incredibly friendly and helpful with recommending great food for all of us. As an avocado toast addict, I was extremely pleased with their rendition on the dish. Loved my chai turmeric latte and enjoyed sitting outside on the sidewalk so that our dogs could hang with us while we ate! When I did pop inside quickly, I appreciated the retro cool aesthetic and the good vibes.

La Neta – An amazing take on Mexican food, the trendy Hoxton Hotel has this restaurant on their ground floor located steps from the edgy hotel bar. They change their menu regularly based on seasonal and local ingredients which is SO cool. When I was there, we sampled chips & guac, yuca tots, kale enchiladas and halibut all of which was incredible.

¿Por Qué No? Taqueria – This incredible Mexican restaurant with both indoor and outdoor seating, you will likely have to wait in a line at this little taco shop. Luckily, the line moves quickly and is definitely worth the wait. With multiple delicious vegetarian taco options, delicious guac and Mexican coke, you can’t go wrong!

Irving Street Kitchen – The best biscuits I’ve ever had in my life complete with ISK famous pepper jelly is reason enough to come and have appetizers at this amazing restaurant. We were extremely hungry this day and had a full set of appetizers along with dinner and every single food I tasted here was amazing. We started with a cheese plate and the biscuit platter followed by local chinook salmon. Just unbelievable. I highly recommend it!

Serratto – This Italian-Mediterranean restaurant was sophisticated and lovely as well as one of the fancier restaurants we went to in Portland. We started our dinner with a delicious appetizer of stuffed piquillo peppers before I had the rich and decadent risotto for my main meal, which was amazing.

Coffee/Tea Places

Stumptown Coffee – The original Stumptown Coffee is from Portland, Oregon! This made a lot of sense after I found out that Portland was called “Stumptown” from the days when it grew so quickly that they left tree stumps all around town as it was developing until the city had enough manpower to get rid of them. This was a wild revelation for me because after living in NYC and having been to the location there, I always assumed that the famous Stumptown Coffee shop in the city was from NYC! The more you know right?! Anyways, I had an amazing iced chai tea latte with almond milk and loved the cool atmosphere of the coffee shop which was the same vibe as the NYC one but much more spacious and therefore containing more art!

Tiki Tea – Right down the street from Proud Mary Coffee where I had the insane Avocado Toast, there is an adorable little shop called Tiki Tea! They have tons of different types of teas but the most exciting of course was the boba tea! My friend and I each got a different flavor so that we could share so I can attest to the fact that both the classic black tea and the matcha with boba were delicious! A perfect little treat for the road to drink and chew on the little tapioca balls while you walk around the neighborhood and check out the shops!

Weekend / Day Trips

I think that some of the coolest, most quintessential Oregon activities (or at least what I, as an outsider, felt were the most quintessential Oregon things to do) happened outside of the actual city of Portland. This requires having a car so if you aren’t lucky enough to have your best friend from college living there, then I recommend renting a car for a few days to hit some of these cool spots!

Day 1

Vista House at Crown Point – If you’re looking for gorgeous sweeping views of a river that is nestled beautifully at the bottom of a gorge, this is the place for you! Topped off with a very cool stone vista house where you can get up even slightly higher to see the view from the top balcony (although tbh, you’re already high enough to see the amazing view from the ground looking over the short stone wall). It is free to enter the vista house although dogs are not allowed inside but they have gorgeous public restrooms – just sayin… – there is also a little bit of information in the downstairs near the restrooms so you can read up on the area a bit as well!

Hood River – This is THE place to go if you’re looking to go to breweries, walk around a cute town, or go kiteboarding while you’re in the Portland area! Hood River has many amazing breweries but since we had a full day of activities planned (we went to the Vista House at Crown Point on our way to Hood River!), we only went to one brewery so that we could be sure to make it to Multnomah Falls that same day as well. It was also raining that day so we weren’t much into walking around the town in the rain but I hear that it is a really cute town to walk around with awesome shops and a great vibe. We spent most of our time at the Full Sail Brewing Company where we had amazing food – like fried Brussels Sprouts and the Impossible burger – and drinks! I had an amazing ginger berry kombucha because I don’t actually like beer. I guess this is a good time to mention that apparently Portland is also known for their breweries but since I don’t like beer I didn’t go to any besides this one… woops!

As I mentioned, Hood River is also very well known for having good wind (especially from May to September) but I’ll be honest with you… I’m a fair weather kiter and much prefer to kitesurf in warm conditions like my favorite place in Cabarete, DR! It was rainy and cold, I would’ve had to wear a wetsuit, and I was with friends so I skipped kiting in Hood River. It was really cool though because from the window at Full Sail Brewing Company we were able to see all of the kiters on the river and watch while we ate and drank!

Multnomah Falls – A quick and easy walk on a casually upward spiraling path, you can get multiple views of the beautiful Multnomah Falls waterfall! You can even walk out on a little bridge that honestly was giving me a little bit of vertigo and bringing out all of the dog mom fears since the bridge had openings large enough for my little pup to fall through – of course she was on her leash but I got so nervous I ended up picking her up and not putting her back down until we got off of the bridge, hehe. But being on the bridge did allow for a much closer look at the falls and awesome pics! Apparently you can often times hike up even higher to reach the top of the falls but for whatever reason that particular path was blocked off when we were there and we couldn’t go farther up than the bridge – not that I was complaining! 🙂

Day 2

Cannon Beach & Haystack Rock – Made famous from “The Goonies” (which btw I’ve never seen…) Haystack Rock is a very cool, massive, beautiful rock in the water right on Cannon Beach! It is unlike anything I’ve ever seen at a beach in the USA. While the temperature and weather at Cannon Beach tends to be a bit chilly (avg temps are 63-66 degrees F which is much colder than the temps in Portland) so the beach isn’t necessarily ideal for sunbathing and swimming, but it is still a very cool place to walk around, stick your toes in the sand, and get a nice walk and view! Who doesn’t like the beach!? Even if it is too cold to swim! 🙂 What I personally think absolutely made our Cannon Beach walk that much more enjoyable, was the presence of my adorable, prancing puppy Rory. Although technically, it says that dogs need to be leashed on the beach, it appears as though they do not enforce this rule because we were at the beach in the middle of the day on a Saturday, police were driving by, and nobody said a word about my dog or any of the other dogs that were all off leash frolicking and chasing each other around gleefully in the sand. The beach was quite large so there was plenty of space for multiple different dogs to run and play fetch without even coming close to each other but of course my little pup loves to run and play with other dogs so she was constantly sprinting back and forth finding dogs who would play with her, digging in the sand, getting her paws wet in the frigid Pacific Ocean and just generally having the time of her life. As I mentioned, walking / jogging around the beach with my dog off leash really enhanced my experience and made it so that I didn’t want to leave even after my fingers and toes were cold (I did not pay attention to the weather situation and showed up in jean shorts and a crop top… thank goodness I had my hoodie with me so at least I wasn’t freezing but pants of some sort would have been a smarter move). Due to my aforementioned cold fingers, when we did finally decide to leave we stopped at a very adorable coffee shop called Sleep Monk Coffee Roasters in Cannon Beach to grab some delicious sweet treats (some sort of chocolate chip banana bread if I remember correctly) and my all time fav warm drink of a chai tea latte with almond milk before jumping back in the car to head on to our next adventure. We drove somewhere else to have lunch before heading back to Portland, but I would actually recommend staying around the Cannon Beach area to have lunch in one of the local places there before doing the 1.5 hour drive back to Portland.

Day 3

Trillium Lake boasting views of Mt Hood – Trillium Lake was such a wonderful and relaxing experience about an hour and a half drive further inland from Portland. We got a late start that day seeing as we were out quite late the night before – karaoke gets us every time – but I’m so glad that we forced ourselves to wake up and make the journey! Trillium Lake is a beautiful pristine lake with an incredible view of the snow-capped Mt Hood. You could see the massive mountain from all areas of the lake and the view never got old! The lake is also surrounded by a 1.9 mile walking trail amidst pine trees although we really only walked in and out of a few pine trees because I much prefer to be on the water! We rented a canoe and enjoyed the afternoon paddling around the lake with my dog, Rory. We were even a little fancy and brought ourselves a cheese and cracker snack to munch on while we floated around the lake! One of the other amazing things was to see the little tadpoles swimming around the lake. In June, they were in their in between being baby tadpoles and becoming frogs stage and therefore had arms, legs and tails! When I saw the first few I thought they were mystical creatures before my friend politely informed me that was what tadpoles looked like when they got older – I had only previously seen baby tadpoles that had tails but no arms or legs!

Plan Ahead Tip!: We booked our canoe rental the day before with Mt Hood Outfitters which was clutch because once you arrive at the lake, there is an access point to get a canoe, kayak or paddleboard into the water, but they don’t have a place on the lake set up with equipment that you can rent. Make sure you are prepared ahead of time and either bring your own, or arrange for it prior to arriving. Mt Hood Outfitters was so easy! Not only, did they arrive when they said they would with the canoe, but they also carried it over and put it in the water for us! They rent out canoes, kayaks & paddleboards all of which would be great on Trillium Lake. We opted for the canoe so that Rory could join as I was a little nervous she would try to jump off of a kayak!

Mt Hood & The Timberline Lodge – After spending all afternoon staring at Mt Hood from the lake, it was time for us to see it up close and personal! We drove the 20 minutes through the windy mountains catching glimpses of Mt Hood here and there between the trees before arriving at the Timberline Lodge at Mt Hood. Not only were parts of “The Shining” filmed at Timberline lodge, but it is also home to delicious food, rustic lodge vibes & it is the main lodge at the only mountain in the US that legit has snow in June and you can ski or snowboard YEAR ROUND! It was almost surreal having been on the lake just an hour prior in a bathing suit to sitting in the Timberline Lodge eating and gazing out the window at the snow covered trees and Mt Hood right out the window. Seeing as it was already getting late and I had my pup to think about, we didn’t even consider trying to ski or snowboard. But I hear that it is amazing and they do really cool snowboarding camps there every summer as well.


Well there you have it folks! That is the Alli Lehr guide to Portland, Oregon and the surrounding areas. I love to see people going to places I’ve recommended so definitely shoot me a DM on Instagram @travelislovexoxoalli if you go to any of these places and let me know what you think!

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