An adventure to Portland, Oregon means to breathe in the details of life, to gain new memories of realization and inspiration, and to be able to live in the moment in every way. Embedded in nature, Portland allows for anyone to beautifully indulge in the day-to-day pieces of life. It captures the essence of inspiration by embracing the concept of “local” (eating locally grown and produced foods, enjoying locally owned stores, and adventures through local landscapes), all along with embracing every detail of seasonal changes.

If you have a day or a week to explore Portland, there are endless possibilities to fill your day(s) to create an inspiring, breath-taking experience. Portland is a smaller city nestled by surrounding hills with the Willamette River running through it. It is a walking (and very bike friendly) city where each turn brings new perspective to life.

Lindy Jacoby_ Portland Sign copy

Portland is rich in culture and life. When visiting you’ll find that the outdoors and indoors tend to blend together. There are multiple hiking areas (in the city and around), but a favorite is the 187 acres with 12 miles of hiking trails at Hoyt Arboretum. To walk through the heart of the city and view the stunning architecture, visit Pioneer Square, the Waterfront Park, or walk across one of the many bridges over the Willamette River. Local shops are everywhere, so you can’t go wrong no matter your location. A few favorite shopping spots are Powell’s Books, which is the kingdom of books, and Nob Hill, which has great shops. Also, Portland Art Museum has a beautiful collection to view.

Eating, and eating locally, is probably one of the locals’ favorite things to do. You won’t be disappointed with the endless possibilities of restaurants. When in Portland, make sure to venture to local restaurants for the best tasting food; they tend to use local product to indulge in the best of Oregon. With the below options, your taste buds will be delighted and surprised. Don’t forget to enjoy the uniquely beautiful environments as well.


Starting your day off right can be done in many ways. Venture to one of the few La Provence locations for a large, sit-down breakfast. For the best donuts go to Blue Star Donuts. If you are looking for great pastries or lighter breakfast, venture to Grand Central Bakery.

Lindy Jacoby _ Blue Star Donuts-2


Locally made drinks are everywhere. Two favorite places to grab coffee and just relax with friends are either any Stumptown Coffee Roasters or Ristretto Roasters locations. Their environments are so unique and the drinks are delicious. They can be found all around Portland. Tea is also abundant in Portland. The best place to grab a cup, or a few cups, of tea is at Smith Teamaker.


No matter your time constraints, there are so many options for a great lunch. For it’s easy menu and outstanding fries visit Little Big Burger. If you are downtown and want a sit-down environment two great places are Olympic Provisions, which have the best-handcrafted meats, and Fire Side, who indulge in local farming.


In Portland, dinner is an event, typically relaxing and drawn out to embrace your environment and enjoy your people. A great restaurant is Veritable Quandary, with a menu constantly changing to fit the season. In the beautifully rustic setting of St. Jack, a French style cuisine is offered. Or visit a local Thai favorite, Pok Pok, which delights all your senses.


After a day full of excellent food, the best way to end it is with some delicious dessert. Salt & Straw serves the best ice cream. If cupcakes are what you are craving, Cupcake Jones is your go to place. Both change their menu every month, with each recipe tasting amazing. If you aren’t sure what your sweet tooth is craving, visit Papa Haydn, which has a wide selection of decadent desserts.

City Overlooks
If you have time, seeing the view of Portland is breath-taking. You can see all the beautiful pieces of Portland, with both Mt. Hood and Mt. St. Helens as a backdrop, at the International Rose Test Garden, Japanese Garden, or a personal favorite, Pittock Mansion.

After a beautifully exhausting day, your mind will want an equally beautiful place to stay. If you want to be in the midst of gorgeous chaos, the Vintage Plaza is right in the center of the city and has stunning interiors. Also downtown, Ace Hotel offers beautifully artistic rooms, just within walking distance from many mentioned locations. If your adventures lay across the river, the Jupiter Hotel offers a modern style and is a great place to rest.

Lindy Jacoby _ Oregon Coast copy

Stretching Your Arms 
One of the very unique qualities of Portland is that it lies in the center of a variety of different landscapes. No matter what direction you want to go, an hour and a half drive will enable you to escape to a brand new environment. Locals do not waste this opportunity: so if your adventure wants to extend a little further than Portland, let it. If you go in one direction, you will hit the snowy and great hikes of Mt. Hood. In another direction, you will hit the Oregon Coast (Cannon Beach is a favorite). You can also see waterfalls that seem unreal (Silver Falls in Salem and Multnomah Falls in the Columbia Gorge are the most well known), in a completely different direction.

When visiting Portland, no matter where your adventures lay, slow down, even if just slightly, to capture those rare moments of just living in the best way.

What are your favorite Portland sights?

Images courtesy of Lindy Jacoby


  1. Wow you look AWE-SOME Karen! You totally pulled off the look. I’m gonna have to try some now, usually I’m kinda intimidated of the SHU store so thanks for throwin out some prices, that helps.And i’m with you on not being able to apply them on myself ugh, I tried it last night and looked ri di cu lous blah!

  2. Yes yes yes! This is my city! I’ve been waiting for you to do a City Guide on Portland for so long! It’s such a gorgeous & beautiful city, & I’m proud to call it home.

    A few more suggestions ((I couldn’t resist)):
    – take a walk down NW 23rd Avenue. It’s one of the classier parts of Portland, & it’s one of my favorite spots.
    – For a late lunch, go to JO Bar & Rotisserie. It’s on NW 23rd, and it’s the lunch//dinner extension of Papa Haydn. Go during their happy hour, & get the $6 fondue. It’s to die for.
    – If you’re into vintage shopping, Hawthorne Blvd is the place to be. For clothes, go to House of Vintage & the Red Light. For kitschy furniture and trinkets, Vintage Pink is the place to be.
    -Visit Schoolhouse Electric. Just…trust me.

  3. This is where we went for our honeymoon. Our favorite was Voodoo Doughnuts. Great flavors and so much fun. Powell’s was one of our favorite days and Stumptown is the best coffee hands down. We had some every morning.

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