Exploring Portland's Neighborhoods by Foot


Despite the fact that my trip to Portland was short, I did my best to explore as many neighborhoods as possible. If you’ve never been to Portland, let’s start with some basic orientation to help get your bearings. The city is divided by the Willamette River, with the more walkable neighborhoods on the west side and the slightly more spacious, residential neighborhoods on the east. If you remember from my recent post, Portland sports every type of bridge architecture so crossing from one side of Portland to the other is the ultimate photo op.

I’ll be starting with two neighborhoods on the west side, from north to south and then will move along to the east side. There are plenty of neighborhoods not mentioned on this list but these five are the ones I spent the most time in, so they are the ones that made the cut!

The Pearl District

We all know how I adore revamped neighborhoods and Portland’s Pearl District has a great rags to riches story. Former warehouse turned stylish hub, this neighborhood is effortlessly charming. The cobblestone streets contrast the modern lofts, showcasing how both old and new influences can exist in perfect harmony. This area is very walkable and feels like a city in that there are cross walks and plenty of fashion boutiques, bars, restaurants and cafes. I highly recommend stopping by Powell’s for a reading break, Blue Star Donuts for a delicious snack and the Multnomah Whiskey library for what will probably be the best cocktail you ever drink. Alder & Co. is the perfect one-stop-shop for unique gifts for your friends back home.

Neighborhood Travel Guide to Portland

Old Town Chinatown

Technically two different neighborhoods, they basically work as one. In fact, the Pearl District connects  to Old Town Chinatown so you can easily visit both neighborhoods in an afternoon. As you get closer to the river, things start to feel a bit more lively. Voodoo Donuts is a must for any new Portland visitor and you can also see some funky street art nearby as well. Also worth visiting is the Lan Su Chinese Garden, which is a walled garden that stretches for a full block. If you’re in town on the weekend, stop by the Portland Saturday Market to shop for artisan crafts, sample exotic dishes or mingle with the locals a bit. Further south you have Portland State University where the Portland Farmers Market takes place every weekend.

Neighborhood Guide to Portland

Central Eastside

If you’re on the hunt for a microbrewery, look no farther than Central Eastside, the area just across the Willamette River from downtown. Beyond the large warehouses and urban train tracks there are a slew of popular restaurants and breweries located in this part of town. It’s also quite the scenic area, as the river is right there and the views are pretty spectacular. Many of the breweries on our Brewvana tour were located in this area like Commons Brewery and Cascade Brewing Barrel House. The cool thing about Portland is that if you continue biking just a few minutes beyond these hotspots, you’ll find yourself in a series of quiet, residential areas. The green grass and tall trees overhead feel like a suburb right in the middle of the city.

Lifestyle in Portland

Mississippi / Williams

Heading over to the east side now, Mississippi / Williams showcases a completely different side of the Portland you thought you knew. I mainly stuck to Mississippi Avenue, a long stretch of trendy bars, up-and-coming restaurants, outdoor beer gardens and quirky shops. The North Williams shops are located about a half mile away, so depending on your endurance level you might want to bike there. Plan ample time to walk around, as each shop is more interesting than the next. Mississippi Records is a small, independent record store selling everything from blues and jazz to some of our favorite rock legends’ albums. Shop for new and vintage clothes for both men and women at Animal Traffic or scarf down some fresh food at the Mississippi Marketplace.

Art guide to Portland

The Alberta Arts District

This neighborhood is an artistic explosion that is ready to happen. Actually, it’s already happening but I sense that even more creativity will appear in the coming years. Similar to the Mississippi Avenue, The Alberta Arts District is a mix of vibrant street art, cool bars, independent fashion boutiques and artisanal bakeries. As soon as I arrived to this area I knew I had found my “place” so to speak. There is so much to see and do here so if time permits, plan a few hours to walk at your leisure. Pie Footwear sells eco-friendly, vegan shoes and if you’re curious as to what that is, you aren’t alone! Gallery hoppers can hit up Monograph Bookweks, HiiH Gallery and Guardino Gallery. For vintage clothes, try Tumbleweed or Frock.

Street art in Portland


This trip was hosted by Travel Portland. All opinions are my own.


Megan McDonough
Megan Eileen McDonough is writer, blogger and social media specialist based in New York City. She also runs Bohemian Trails, a lifestyle blog designed for the savvy and stylish traveler. Bohemian Trails aims to feature must-see places around the world, covering everything from revamped neighborhoods and vibrant street art to innovative tech hubs and everything in between. Her cultural escapades have taken her to Latin America, Asia, Europe, and the Middle East.

Megan is also a freelance writer and social media specialist based in New York City. She contributes to various online and print publications in the travel and fashion industries and is an international correspondent for both Jetsetter and Northstar Travel Media.
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