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A Complete Itinerary for Spending a Full Day in Downtown Portland, Mapped

  |  Neighborhood Insight, Portland

Taking on downtown Portland can feel overwhelming as you attempt to navigate the many restaurants, coffee shops, bars, boutiques, parks and various attractions lining the streets. We removed the guessing game with this complete guide to spending a day in downtown Portland, so you can spend less time searching on Google Maps and more time soaking in all this city has to offer.

You can either follow our step-by-step itinerary to a T or simply glean a few ideas to enhance your day in downtown! Either way, we created an interactive map so you can envision your path from one place to the next. Most stops are close enough to walk to, but you might consider picking up a bike from Biketown or hopping on a Bird, Lime or Spin scooter if the distances are too far to conquer on foot.

There is so much to see, taste and experience in downtown Portland. Enjoy your day exploring the city!


8 a.m. | Start With Coffee

Stumptown Coffee Portland, OR

Every good day starts with coffee. And thankfully, Portland knows how to do coffee right. After all, there are roughly 737 coffee shops in Portland, 600 of which are independent. So if you put “coffee” into Google Maps while standing in downtown, you’ll be pretty overwhelmed with all of the options. Might we suggest Heart Coffee, Stumptown, Upper Left, Courier or Coava? Not only do each of these coffee shops serve exceptional coffee, they are all within reasonable walking distance of our next stop: brunch.


9 a.m. | Enjoy Brunch at Tasty n Alder

You don’t have to wait until the weekend to enjoy brunch in downtown Portland. That’s because Tasty n Alder serves up a mean brunch every single day of the week, which means you can fulfill your mimosa and omelet cravings on a Tuesday. Served daily from 9 a.m. to 2 p.m., their brunch menu features brunch cocktails and coffee drinks, plus a variety of food options, from smaller plates and sides to large plates and boards. The cozy, industrial atmosphere at Tasty n Alder makes this the perfect place to kickstart your day in downtown Portland.


10 a.m. | Visit a Museum

Make your way to the Portland Art Museum or the Oregon Historical Society Museum, which are located just steps away from each other! Or attempt both, if you have extra time and want an equal dose of both art and history. The Portland Art Museum is the oldest art museum on the West Coast and the seventh oldest in the country! But this old museum is always filled with new and exciting exhibits, including more than 50,000 objects displayed in 112,000 square feet of galleries, covering art from ancient times to the modern day. The Oregon Historical Society Museum offers three floors of both permanent and traveling exhibitions, exploring the people, places and events that have shaped the history of Oregon and America.

After your museum visit(s), take a stroll through the beautiful Shemanski Park, a skinny-but-very-long park covered in a canopy of trees wedged between the museums. If your visit falls on a Saturday between May and October, you’ll also encounter the Shemanski Park Farmers’ Market!


12 p.m. | Pick Up Lunch at a Food Cart

It’s time for lunch! And in true Portland fashion, that means it’s time to track down the nearest food cart. An easy way to choose from a variety of food styles is by going to a food cart pod. The famous Alder Street Food Cart Pod is in the midst of finding a new home, but the Fifth Avenue Food Cart Pod and the Third Avenue Food Cart Pod are two excellent options! No matter what type of food you’re craving, you’re likely to find it here.


1 p.m. | People Watch at Pioneer Courthouse Square

Pioneer Courthouse Square Portland, OR

2019 Festival of Flowers Paint The Town, Designed by Walker Macy
Photo Courtesy of Pioneer Courthouse Square

Whether you end up at the Fifth Avenue or Third Avenue Food Cart Pod, you won’t be far from Portland’s living room, also known as Pioneer Courthouse Square. This 40,000-square-foot city block in the heart of downtown is the perfect place to do some people watching — or enjoy your food cart food al fresco. On a sunny day, the square is filled with people reading, walking, drinking coffee and enjoying the buzz of activity in the heart of the city. Plus, Pioneer Courthouse Square hosts more than 300 events per year, so there’s a good chance you might stumble upon one during your visit!

While you’re here, take a moment to read up on the history of the square, which dates all the way back to 1849.


2 p.m. | Stop for a Sweet Treat

After your lunch has settled a bit, you might be craving a sweet treat. If so, make your way to one of the many sugar providers in the city. If you’re craving ice cream, we recommend Wiz Bang Bar by Salt & Straw, which is conveniently on your way to the next stop. But if you’re craving a doughnut, Voodoo Doughnut is also on your way to the next destination! Alternates for both include Ruby Jewel Ice Cream and Blue Star Donuts, which are both a little out of the way but well worth the detour.


2:30 p.m. | Visit Lan Su Chinese Garden or Tom McCall Waterfront Park

Lan Su Chinese Garden Portland, OR

Photo Courtesy of Lan Su Chinese Garden

Escape to a serene oasis in the heart of the city with a visit to Lan Su Chinese Garden, considered the most authentic Chinese garden outside of China. This 40,000-square-foot garden in Chinatown is a window into Chinese culture, history and way of thinking. We recommend stopping by the Teahouse in the Tower of Cosmic Reflections, where you can sit, relax, and enjoy tea while gazing into the lush garden. If you’re pressed for time, take a stroll by the water at Tom McCall Waterfront Park, which runs alongside the Willamette. This expansive park is a great place to rest your legs, watch boats float by, and look out on the water.


4 p.m. | Go Shopping + Visit Powell’s City of Books

Just like us, Portland is very passionate about all things local. Experience this local focus at the many small businesses and boutiques dotting the city. There’s a particularly excellent selection of shops near Powell’s City of Books, which is our next stop on the itinerary. This book empire in the Pearl District occupies an entire city block and houses over one million books. Peruse their massive collection throughout nine color-coded rooms with over 3,500 different sections varying in topic.

Before you make your way inside this iconic bookstore, pay a visit to a few shops in and around Union Way, including Frances May, Bridge & Burn, Tender Loving Empire, Tanner Goods, Adorn, North of West, and West End Select Shop.


6 p.m. | Enjoy Dinner on a Rooftop

Take your everyday dinner experience to new heights by dining at Departure Restaurant + Lounge, a pan-Asian restaurant and bar floating atop the landmark Meier & Frank Building. One of our favorite rooftop patios in the city, Departure offers an elevated dining experience with breathtaking city views all around. Not to mention, Chef Gregory creates exceptional modern pan-Asian dishes available on their dinner menu, complemented by creative cocktails.

PS If you get there a bit early, you might make it in time for their happy hour, offered every day from 4–6 p.m.!


7:30 p.m. | See a Show

Top off the day with a show at one of the many venues in downtown Portland. If you’re looking for a play or musical, check the calendars for Portland Center Stage at The Armory, Keller Auditorium, or Newmark Theatre. If you’re hoping to catch a concert or some sort of musical performance, check out Arlene Schnitzer Concert Hall, The Old Church Concert Hall or Crystal Ballroom.


10 p.m. | Discover a Speakeasy

Botanist Bar Portland, OR

Photo Courtesy of Botanist Bar

Wind down with a cocktail or two inside one of the city’s most secretive watering holes. You may not be aware that there are a number of speakeasies in our midst, several of which are located right here in downtown. Use our guide to speakeasies in Portland to learn more about Pépé le Moko, the Multnomah Whiskey Library and Botanist Bar.


That’s a Wrap!

What must-visit destinations would you add to the itinerary? Let us know in the comments below.

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About the Author

Melissa Peterson, Director of Agent Services and Technology

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