72 Hours in Portland, Oregon: The Best Weekend Guide

Portland, Oregon is a vibrant city that effortlessly blends natural beauty with a unique urban charm. Located in the Pacific Northwest, Portland is renowned for its lush green spaces, mouthwatering food scene, and culture that celebrates creativity and sustainability. Whether you're an outdoor enthusiast eager to explore scenic trails or chase waterfalls, a foodie on the hunt for the next culinary adventure, or a culture buff ready to dive into the local arts scene, Portland has something to captivate every visitor.

Portland is a quick 2-hour flight from San Diego, making this city a great place for a long weekend getaway.  In this post, I'll share the must-visit spots and the best things to do during a trip to Portland. 

Best Stay: The Duniway Portland

Nestled in the heart of downtown, the Duniway Portland Hotel offers a distinctive blend of modern luxury and classic charm. The hotel features elegantly appointed rooms and suites, each thoughtfully designed with plush bedding, state-of-the-art amenities, and stylish decor that reflects the vibrant energy of Portland. Guests can indulge in culinary delights at the hotel's signature restaurant and sip coffee in the cafe near the lobby. 

The Duniway's prime location provides easy access to some of Portland's iconic attractions and neighborhoods. Just steps away from the hotel, visitors can explore the bustling Pioneer Courthouse Square, often called Portland's living room, home to several local food carts. 

The hotel's proximity to the city's MAX light rail system and other public transportation options makes it an ideal base for exploring the wider Portland area. Whether you're visiting for business or leisure, the Duniway Portland Hotel offers a unique and luxurious experience that captures the essence of this eclectic and dynamic city.

Best Brunch: Screen Door Pearl District

This was my favorite place to eat brunch in Portland. The menu at Screen Door excels in delivering mouth-watering Southern classics. I ordered the Fried Chicken Sandwich, the chicken was so tender and flavorful. I also tried their cinnamon roll and it was so delicious, not overly sweet, and just the right amount of icing. 

 Among the must-try dishes is the iconic Screen Door Fried Chicken, which boasts a perfect blend of crispy, flavorful batter, and tender, and juicy meat.  The Chicken and Waffles, are a harmonious combination of sweet and savory. For those with a sweet tooth, the Bananas Foster French Toast is a decadent treat that perfectly caps off a satisfying meal. Whether you’re in the mood for a hearty breakfast, a leisurely brunch, or a comforting dinner, Screen Door in the Pearl District promises an exceptional dining experience that celebrates the best of Southern cuisine.

Best Urban Hiking: Macleay Park to Pittock Mansion

Macleay Park is a beautiful urban park located in near downtown Portland and is one of the largest urban forests in the U.S. It is known for its dense woodlands and peaceful trails. One of the most popular trails is the Macleay Park to Pittock Mansion Trail. The Macleay Park to Pittock Mansion Trail is a must-visit 5-mile out-and-back hike in Portland for those seeking a blend of natural beauty and historic charm. The trail winds through lush forest, following Balch Creek and leading hikers past towering trees and occasional wildlife. The highlight of the hike is reaching Pittock Mansion, a historic estate perched on a hill with panoramic views of downtown Portland, Mount Hood, and the Cascade Range. The view is named one of the best views in Portland!

Best Unique Foodie Experience: Portland Food Carts

Before I visited Portland, I had no idea that Portland is one of the best cities to visit for foodies! The city is famous for its vibrant food cart (food carts are similar to food trucks) scene, offering a diverse range of culinary delights from all over the world. These food carts are scattered across the city in various "pods," or clusters, where you can find everything from gourmet burgers and authentic Thai dishes to vegan treats and freshly brewed coffee. The food cart culture in Portland is all about creativity, affordability, and supporting local businesses, making it a favorite among both locals and tourists.

Best Local Market: The Portland Saturday Market

 The Portland Saturday Market is one of the largest continuously operating outdoor arts and crafts markets in the U.S. Located in the Old Town Chinatown district along the waterfront, it runs every Saturday and Sunday from March through December. The market features over 150 local vendors offering a wide range of handcrafted goods, from jewelry and clothing to home décor and artwork. In addition to shopping, visitors can enjoy live music, street performances, and a variety of food stalls serving international and local cuisine

Best Waterfall: Multnomah Falls 

This is one of those experiences that is worth the visit and lives up to the hype! Multnomah Falls is one of the tallest year-round waterfalls in the United States and is the most visited nature site in the Pacific Northwest. Just a short drive from Portland, this iconic waterfall in the Columbia River Gorge offers a challenging yet rewarding hike to the top, with stunning views of the falls and gorge along the way. The trail to the top of the waterfall is about 2.3 mi, a paved trail with a steady incline and switchback. The views at the top are amazing! This is easily one of the best waterfalls I’ve seen in the U.S. and one of my favorite things I did during my trip to Portland.

Best road trip from the city: Oregon Coastline

The Oregon Coast is a breathtaking destination known for its rugged cliffs, sandy beaches, and charming seaside towns, making it an ideal escape from the city. The drive from Portland to the coast is just as scenic as the destination, typically taking about 1.5 to 2 hours depending on your coastal stop. Along Highway 26 or Highway 6, travelers pass through dense forests, rolling hills, and lush farmlands before reaching the dramatic coastline. Once there, you can explore iconic spots like Cannon Beach with its famous Haystack Rock. I recommend stopping at a local ice cream shop serving Tillamook ice cream! 

A weekend getaway in Portland, Oregon, is the perfect way to experience the city’s vibrant culture, stunning natural beauty, and rich history. Whether you’re hiking through Macleay Park, exploring shops and eating delicious food at one of the food cart pods, or enjoying the art and craft treasures at the Portland Saturday Market, this city offers something for every traveler. With so much to do and see, Portland promises an unforgettable weekend filled with adventure, relaxation, and discovery.