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The Ultimate Guide To Portland In A Weekend: Eat, Stay & Play


Modified: December 28, 2023

by Rodie Rocha



Welcome to Portland, the vibrant and eclectic city nestled in the heart of Oregon. Known for its breathtaking natural landscapes, thriving arts scene, and culinary delights, Portland is a must-visit destination for any adventurous traveler. Whether you’re planning a quick weekend getaway or a longer stay, this ultimate guide will help you make the most of your time in the city.


With its lush green forests, magnificent mountains, and picturesque rivers, Portland offers a plethora of outdoor activities for nature enthusiasts. From hiking the iconic Columbia River Gorge to biking along the scenic Willamette River, there’s something for every outdoor enthusiast to enjoy. And if you prefer to explore the city’s urban landscape, you’ll find an array of museums, galleries, and shops showcasing Portland’s unique arts and culture.


But it’s not just the natural beauty and cultural offerings that make Portland special. The city is also renowned for its world-class dining scene. From trendy food carts serving up international street food to award-winning restaurants utilizing locally sourced ingredients, Portland is a foodie’s paradise. Whether you’re craving artisanal donuts, farm-to-table cuisine, or mouthwatering seafood, you’ll find it all in Portland.


When it comes to accommodations, Portland has options to suit every traveler’s tastes and budget. From luxurious hotels with stunning city views to cozy bed and breakfasts nestled in charming neighborhoods, there’s a perfect place to rest your head after a day of exploring. And with its convenient public transportation system, getting around the city is a breeze.


In this comprehensive guide, you’ll find recommendations on where to eat, where to stay, and where to play during your weekend in Portland. So grab your walking shoes, pack your appetite, and get ready for an unforgettable adventure in the City of Roses!


Where to Eat

Portland is a food lover’s paradise, boasting a diverse culinary scene that caters to all tastes and budgets. From food carts to fine dining establishments, the city offers a wide range of dining options that are sure to satisfy even the most discerning palate.


One of the unique culinary experiences that Portland is famous for is its food cart scene. These mobile eateries are scattered throughout the city, offering a diverse array of cuisines from all around the world. From mouthwatering Thai street food to authentic Mexican tacos, you can find it all in Portland’s food carts. Some popular food cart pods to explore include the Alder Street Food Cart Pod and the Cartopia Food Cart Pod.


If you’re looking for a true taste of the Pacific Northwest, be sure to try the local seafood. Portland’s proximity to the coast ensures that the seafood served in the city is incredibly fresh and of the highest quality. Head to places like Jake’s Famous Crawfish or Olympia Oyster Bar for a delectable seafood feast.


For those seeking a farm-to-table dining experience, Portland has no shortage of options. The city’s commitment to sustainability and locally sourced ingredients is evident in the many farm-to-table restaurants scattered throughout the city. Restaurants like Ned Ludd and Farm Spirit focus on showcasing the best of Oregon’s seasonal produce in creative and innovative ways.


No trip to Portland would be complete without indulging in the city’s famous donuts. Voodoo Doughnut is a must-visit for its quirky and creative donut flavors. From the iconic Voodoo Doll donut to the decadent Bacon Maple Bar, you’ll find a wide selection of unique and delicious treats to satisfy your sweet tooth.


For those looking for a fine dining experience, there are plenty of upscale restaurants in Portland that offer exquisite cuisine paired with impeccable service. Le Pigeon and Beast are two notable establishments that have gained recognition for their innovative menus and exceptional dining experiences. These restaurants are perfect for a special occasion or for those seeking a memorable culinary adventure.


Regardless of your culinary preferences, Portland’s food scene has something for everyone. From street food to fine dining, the city’s diverse range of restaurants ensures that every meal will be a delightful and satisfying experience.


Where to Stay

When it comes to accommodations, Portland offers a wide range of options to suit every traveler’s needs and preferences. Whether you prefer luxury hotels, budget-friendly hostels, or cozy bed and breakfasts, you’ll find the perfect place to rest your head during your stay in the city.


If you’re looking for a luxurious and upscale experience, Portland has several renowned hotels that offer top-notch amenities and exceptional service. The Nines, located in the heart of downtown, is a five-star hotel known for its elegant rooms, stunning rooftop views, and world-class dining options. The Heathman Hotel is another upscale option, featuring beautifully appointed rooms and a rich literary history.


If you’re traveling on a budget, there are plenty of affordable accommodations in Portland as well. Hostels like the HI Portland Northwest Hostel and the HI Portland Hawthorne Hostel offer clean and comfortable accommodations at a fraction of the price of a hotel. These hostels also provide a great opportunity to meet fellow travelers and exchange tips and recommendations.


For those seeking a more intimate and charming experience, Portland is home to many unique bed and breakfasts. The Lion and the Rose Victorian Bed and Breakfast and the Portland’s White House are both elegant and historic options that offer cozy rooms and personalized service. These bed and breakfasts provide a home-away-from-home atmosphere and are a great choice for travelers who appreciate a more personal touch.


If you prefer to be in the heart of the action, staying in downtown Portland is a great option. This area is bustling with shops, restaurants, and entertainment options, making it a convenient base for exploring the city. The Ace Hotel and the Hotel Lucia are two popular choices in the downtown area, offering stylish accommodations and easy access to the city’s attractions.


For those who want to be surrounded by nature, there are also accommodations available in the outskirts of Portland. The Columbia River Gorge area offers beautiful lodges and cabins with stunning views of the gorge and easy access to outdoor activities like hiking and exploring waterfalls.


Regardless of where you choose to stay in Portland, you can be assured of a comfortable and memorable experience. The city’s diverse range of accommodations ensures that there is something for every traveler, whether you’re seeking luxury, affordability, or a unique and charming atmosphere.


Where to Play

Portland is a city that offers endless opportunities for entertainment and exploration. From vibrant neighborhoods to beautiful parks, there’s no shortage of things to see and do during your visit. Here are some recommendations on where to play in Portland:


1. The Pearl District: This trendy neighborhood is known for its art galleries, boutiques, and hip restaurants. Take a stroll along the streets and discover unique local shops, grab a coffee at one of the artisanal cafes, or explore the contemporary art scene at places like the Elizabeth Leach Gallery.


2. Washington Park: Located in the West Hills, Washington Park is a sprawling green space that offers a variety of attractions for outdoor enthusiasts. Visit the world-renowned International Rose Test Garden, explore the enchanting Japanese Garden, or take a scenic hike through the park’s extensive trail network.


3. Pioneer Courthouse Square: Known as “Portland’s Living Room,” this vibrant square hosts numerous events and festivals throughout the year. Relax on the steps, catch a live performance, or simply people-watch while enjoying the bustling atmosphere.


4. Powell’s City of Books: Bookworms will rejoice at the sight of Powell’s, the largest independent bookstore in the world. Lose yourself among the shelves, browse through a vast selection of new and used books, and immerse yourself in the literary haven that spans an entire city block.


5. LANE COUNTY FAIR: Every summer, the Lane County Fair offers a fun-filled experience for all ages. Enjoy thrilling rides, indulge in tasty fair food, marvel at the livestock exhibits, and catch live performances by various artists and musicians.


6. Portland Saturday Market: Visit the nation’s largest weekly open-air crafts market and immerse yourself in the vibrant atmosphere. Browse through the stalls, shop for unique handmade crafts, jewelry, and artisanal goods, and savor delicious local food from the food carts.


7. Oregon Museum of Science and Industry (OMSI): Perfect for families and science enthusiasts, OMSI showcases interactive exhibits, hands-on experiments, and an IMAX theater. Discover the wonders of science, explore the universe, and participate in educational programs that cater to all age groups.


8. Portland Art Museum: Immerse yourself in the world of art at the Portland Art Museum. With an extensive collection of contemporary and classical works, the museum showcases pieces that span various cultures and time periods.


These are just a few of the many attractions and activities that await you in Portland. Whether you’re interested in exploring the city’s cultural scene, venturing into the outdoors, or simply immersing yourself in the vibrant atmosphere, Portland offers an abundance of opportunities for play and discovery.


Day 1: Exploring Downtown Portland

Start your first day in Portland by exploring the vibrant and lively downtown area. This bustling part of the city is known for its unique shops, delicious food, and cultural attractions. Here’s a suggested itinerary for your day of exploration:




Begin your day with a visit to Powell’s City of Books, a must-see landmark for any book lover. Lose yourself among the stacks in this iconic bookstore and discover a wide selection of new and used books across multiple genres and topics. Take your time exploring the different sections, grabbing a cup of coffee from the onsite café, and immersing yourself in the literary paradise that spans an entire city block.


Afterward, head towards the waterfront area and visit the Tom McCall Waterfront Park. This scenic park stretches along the Willamette River and offers stunning views of the city skyline. Take a leisurely stroll along the waterfront, breathe in the fresh air, and admire the beautiful scenery.




For lunch, head to the food carts at the Alder Street Food Cart Pod. This iconic gathering of food carts offers a wide range of cuisines from around the world. Whether you’re craving a gourmet grilled cheese sandwich, authentic Thai street food, or mouthwatering tacos, you’ll find it all here. Grab your lunch and enjoy it in the nearby Director Park, an urban square with outdoor seating and a fountain.


After lunch, take a walk through downtown Portland’s shopping districts. Explore the trendy boutiques, local shops, and galleries in the Pearl District and downtown core. Visit Powell’s Books for Home and Garden, a satellite store located near the flagship location, which focuses on home improvement and gardening books.




As the day turns to dusk, make your way to Pioneer Courthouse Square, also known as Portland’s Living Room. This bustling square hosts various events and street performers. Grab a cup of coffee from a nearby café, find a spot on the steps, and enjoy the lively atmosphere.


Afterward, indulge in some delicious cuisine at one of Portland’s acclaimed downtown restaurants. Whether you’re in the mood for farm-to-table fare, fresh seafood, or international cuisine, downtown Portland caters to all tastes. Visit a restaurant like Higgins for a taste of Pacific Northwest flavors or Departure for Asian-inspired dishes with a view from their rooftop patio.


End your day with a visit to a local bar or brewery. Downtown Portland is known for its craft beer scene, so take the opportunity to taste some of the region’s best brews. Explore breweries like Deschutes Brewery or go on a beer-centric pub crawl to discover hidden gems.


Day 1 in downtown Portland promises to be a day filled with exploration, good food, and cultural discoveries. Take your time to soak in the vibrant atmosphere and immerse yourself in the heart of the city.


Day 2: Exploring the Outdoors

On your second day in Portland, venture out of the city center and immerse yourself in the breathtaking natural beauty that surrounds the area. From stunning waterfalls to lush forest trails, there are plenty of outdoor activities to enjoy. Here’s a suggested itinerary for exploring the outdoors:




Start your day early and drive east towards the Columbia River Gorge, a scenic area known for its majestic waterfalls and stunning vistas. Your first stop should be Multnomah Falls, one of Oregon’s most iconic landmarks. Marvel at the powerful 620-foot-tall waterfall and hike the trail up to the Benson Bridge for a closer look. Don’t forget to snap some photos of the picturesque scenery before continuing your journey.


After exploring Multnomah Falls, continue driving along the Historic Columbia River Highway and make stops at various other waterfalls in the area, such as Wahkeena Falls and Horsetail Falls. Each waterfall offers a unique and beautiful sight, and many have short hiking trails that provide stunning views of the surrounding landscape.




Once you’ve had your fill of the waterfalls, head to the town of Hood River, located along the Columbia River. Known for its vibrant outdoor scene and thriving windsurfing community, Hood River offers a variety of activities for adventure enthusiasts. Take a leisurely stroll along the Hood River Waterfront Park and enjoy the panoramic views of the river and surrounding mountains. If you’re feeling adventurous, consider renting a paddleboard or kayak to explore the river on your own.


For lunch, head to one of the local eateries or food trucks in Hood River, where you can indulge in fresh and delicious cuisine with a view. Many restaurants in the area focus on using local and seasonal ingredients, offering a true taste of the Pacific Northwest.




After a day of outdoor exploration, make your way back to Portland and end your day with a relaxing and scenic experience. Visit the International Rose Test Garden in Washington Park, where you can stroll through beautifully manicured gardens and admire an extensive collection of roses. From vibrant reds to delicate pinks, the colorful blooms are a sight to behold.


If you have time, explore more of Washington Park and visit the nearby Portland Japanese Garden. This serene and tranquil oasis offers a peaceful escape from the city and showcases traditional Japanese landscaping and architecture. Take a leisurely walk through the garden and immerse yourself in the beauty and tranquility of this cultural gem.


End your day by enjoying a delicious dinner at one of Portland’s farm-to-table restaurants. Indulge in the flavors of the region and savor dishes crafted with locally sourced ingredients. Toast to an incredible day of outdoor exploration and take in the memories of Oregon’s natural wonders.


Day 2 in Portland, dedicated to exploring the outdoors, promises to be a day filled with awe-inspiring landscapes, refreshing hikes, and tranquil gardens. Embrace the beauty of nature and create lasting memories in the great outdoors.