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3-Day Itinerary Adventure to Portland, Oregon

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Portland, Oregon, lovingly dubbed the "City of Roses" and famous for its quirky "Keep Portland Weird" vibe, is a perfect blend of urban charm and natural beauty. Over three days, you can explore its vibrant downtown, cultural must-sees, and stunning ...
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Day 1 - Downtown Portland and Tom McCall Waterfront Park Area

Get ready to kick off your Portland adventure! The city greets you with its vibrant energy, a blend of urban creativity, natural beauty, and a laid-back charm that’s hard to resist. From exploring quirky neighborhoods to indulging in a food scene tha...

 
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Mill Ends Park—it’s officially the world’s smallest park, but worth it just for the story. At just 452 square inches, this pint-sized park is a quirky gem right in downtown Portland, located in the median of SW Naito Parkway. It's not just its size t...
Mill Ends Park
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If you’re a book lover (or even if you’re not), Powell’s City of Books is one of the most iconic book stores and feels really magical. This isn’t just a bookstore—it’s the largest independent bookstore in the world, taking up an entire city block and...
Powell's City of Books at Burnside: Downtown Portland Bookstore
 
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If you're craving something healthy yet delicious, you’ve *got* to check out Kure Superfoods! This spot is all about treating yourself well with nutrient-packed, wholesome eats—no junk, just great vibes and even better food. With multiple locations a...

I’m obsessed with their superfood smoothies—try the "Morning Glory" with almond butter, banana, dates, and hemp protein! Oh, and their snack bars are next-level good—the perfect on-the-go treat while you’re adventuring. It’s healthy indulgence at its...
Kure Superfoods — Treat Yourself Well™
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If you’re visiting Portland, stopping by Voodoo Doughnut is basically a rite of passage! This quirky, world-famous doughnut shop serves up some of the most creative and delicious treats you’ll ever try. From their signature Voodoo Doll doughnuts to w...

But it’s not just the doughnuts that make this place special—it’s an experience. Voodoo Doughnut is an iconic part of Portland’s quirky charm, and their locations are a visual treat filled with color, personality, and a little bit of magic. Fun fact?...
Voodoo Doughnut - The magic is in the hole! -
 
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When I visited Portland several years ago, this was the first place I ever had “restaurant” ramen (I was a broke college girl and up until that point, only knew about Top Ramen and cup-o-noodles), and this was mind-blowing. 

It's inside the bustling Pine Street Market downtown, this eatery serves up some of the most flavorful Japanese ramen and crispy fried chicken you'll find in the city. Known for its dedication to authentic tastes and fresh ingredients, Matsunoki Rame...
Matsunoki Ramen
 
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Portland has some of the most breweries per capita, and they are worth a visit. If I had to choose, it'd be Backwoods and Deschuttes, both for their broad selection and bites.
Portland: Menus - Backwoods Brewing Company - Brewpub
 
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Deschuttes is the other must-try, for the vibes and local beers on tap.
Welcome to Portland Public House!
 
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Portland food trucks walked so the rest of the country's food trucks could run. Seriously, this city took such a niche concept and made it a blossoming part of the community, perfect for anyone who can't decide what they want. Try it all, truly!
Food Cart Pods | The Official Guide to Portland
 
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This is a little hidden gem in the Pearl District that feels so intimate and the sushi is amazing.
Momoyama - Pearl district, Portland, OR

Day 2 - Nature and Culture around Portland

Portland is incredible because you get the best of the city, with nature surrounding you whenever you want a break. Portland is a city where nature and culture come together in the most delightful way. With lush forests, cascading waterfalls, and the...

 
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Often called the most authentic Japanese garden outside of Japan, this lush oasis is a feast for the senses. Wander through perfectly manicured landscapes, serene koi ponds, and artfully placed stone pathways that feel like stepping into a postcard. ...
Portland Japanese Garden
 
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Stop by the International Rose Test Garden—it’s an icon! With over 10,000 rose bushes and 610 breathtaking varieties, this stunning garden is bursting with color and fragrance from late spring through fall. It’s not just pretty—it’s also part of hist...
International Rose Test Garden
 
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This leading theater company in the Pacific Northwest brings stories to life in the most creative and powerful ways. From classical plays to contemporary works and even lively musicals, their lineup is always diverse and inspiring. Housed in the stun...
Homepage | Portland Center Stage
 
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This iconic Portland spot goes beyond being a traditional zoo—it’s a champion for wildlife conservation. Home to over 230 species, including elephants, lions, and even some adorable arctic foxes, it’s a place where you can truly marvel at the wonder ...
Oregon Zoo
 
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The Pearl District is Portland's haven for art enthusiasts, packed with creativity and inspiration around every corner. Home to an incredible array of galleries, this neighborhood showcases everything from contemporary masterpieces to traditional art...
Art Galleries in Portland's Pearl District - Explore The Pearl
 
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It's a farmer's market paradise right in the heart of Portland, Oregon. It's also known as the largest continuously operating open-air arts and crafts market in the United States, it's a hub of creativity and community. Here, you'll find an incredibl...
Portland Saturday Market

Mount Hood

Mount Hood stands proudly as Oregon’s tallest peak and a natural treasure. Just a short drive from Portland, this iconic destination offers something magical in every season. From skiing and snowboarding on powdery slopes in winter to hiking trails s... 

 
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About an hour outside of Portland standing as Oregon’s tallest peak, Mount Hood is an adventure waiting to happen. Whether you’re hiking through wildflower-filled meadows in the summer, skiing fresh powder in the winter, or soaking in the vibrant fal...
Mount Hood
 
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Tamanawas Falls Trail is a must-visit destination for anyone exploring the Mount Hood region. This picturesque hike, located just a short drive from Hood River, takes you through a lush forest of towering firs and cedars alongside the calming sounds ...
Mt. Hood National Forest - Tamanawas Falls Trail #650 A
 
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Known as the area's premier provider of adventure rentals and guided tours, they offer a wide range of activities to suit every taste for excitement. From the thrill of snowmobile tours and serene snowshoeing treks in the winter to invigorating hikin...
Ultimate Outdoor Adventure Partner | Mt. Hood Outfitters