Itinerary for a Weekend in Portland Oregon
Portland Oregon is a fun, quirky city on the Columbia River Gorge. It makes a perfect weekend trip from anywhere on the United States west coast. This guide to a weekend in Portland Oregon include where to stay, what to do, what to eat, and other tips to plan the perfect 3 day itinerary.
As a Seattleite, I’ve visited Portland many times. Most recently, I spent a weekend in Portland with friend and family. We enjoyed great food, beer, and a bit of nature. Keep reading to plan your own weekend in Portland.
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What to Do in a Weekend in Portland
Portland Saturday Market– If you are visiting over the weekend, be sure to check out the Portland Saturday Market at the Tom McCall Waterfront park, a large outdoor market that runs year-round. Check out art from local vendors and be sure to try an elephant ear dessert or enjoy wandering around for free.
Brewery Hopping– As mentioned above, Portland is full of microbreweries. Spend an afternoon brewery hopping or take an official brewery tour. My two favorite breweries in Portland are 10 Barrel and Deschutes, so be sure those are on your list.
Peddle Tavern– If you want to participate in the beer culture in a unique way, tour on the peddle tavern where you can drink and bike around the city with friends.
Nike Company Store– The Nike swish is the unofficial logo of Portland with how many people wear the apparel or work for the company. If you know an employee, snag a guest pass to the company store for discounts on the newest gear.
Multnomah Falls– This large waterfall is the perfect half-day trip from Portland to escape the city and see some of the beautiful PNW nature. Be aware that this is a very touristy destination, so there will be crowds. Regardless, the fall is beautiful and is worth the trip.
Powell Bookstore– The largest independent bookstore in the world is a must visit during your weekend in Portland Oregon. The rows of books are lined up further than your eye can see, and they have every genre and topic imaginable. Whether you buy a book or simply peruse the store, it is well worth a visit.
Where to Eat in Portland
Portland is definitely a foodie city. There are many amazing restaurants that range from fine dining to food truck roundups. On vacation, I tend to eat on the model of brunch, afternoon snack, and dinner, so the recommendations below are broken down the same way. If you are a lunch person, I recommend checking out any of the amazing food trucks scattered around the city.
Breakfast & Brunch
Brix Tavern– Brix has bottomless mimosas for $11! If that doesn’t convince you to visit, the food is also fantastic. I love their steak or ham skillets, or the brix benedict made with corn cakes. They have a large outdoor seating area for good weather, and a chic indoor setting for the colder months.
Voodoo Doughnuts– In Portland, you need to eat doughnuts. Voodoo doughnuts is the most famous with voodoo doll doughnuts, cereal covered doughnuts, and other unique varieties. The line will set you back an hour, and many think its overrated, but I recommend trying Voodoo at least once.
Blue Star Donuts– Most locals will tell you that Blue Star Donuts are the far better option than Voodoo. I say try both! If you want insta-worthy, over-the-top, doughnuts, go to Vooodoo. If you want simple, high-quality ingredients, go to Blue Star.
Stumptown Coffee– As the southern neighbor to Seattle, Portland takes equal pride in their coffee culture. For the best local coffee brand, check out Stumptown coffee. Comment below if you think its better than Starbucks!
Dinner
Carlitas– Carlitas serves fantastic modern Mexican food and margaritas. They have a Margarita bottle that serves 4-6 people and comes in a variety of flavors. I recommend ordering that, the elote, and 2-3 tacos for your meal.
Luc Lac– Luc Lac is a local favorite for Vietnamese. Their entire menu is fantastic for eat-in or takeout. I’ve tried the beef pho, wontons, spring rolls, and beef vermicelli bowl and loved all of it!
Grassa– Grassa has a simple and affordable menu of fresh, homemade pasta dishes. Order your favorite and it will transport you to Italy.
Huber’s– Huber’s is the oldest restaurant in Portland, with an old-timey, speakeasy vibe. Make a reservation for the back room for the best ambiance. Order a fun cocktail and the beef stroganoff with mashed potatoes, or any other comforting main dish.
Downtown Bars
Vault– The Vault is a super fun bar in downtown Portland. The bar is dark and moody with a large, purple lit bar. Stop by after dinner for a craft cocktail to round out the night.
Departure– No Portland weekend is complete without seeing a view of the city from above. Departure is a great Asian restaurant and bar that is an experience. Enjoy their indoor or outdoor seating options for a drink or even dinner.
Portland City Grill– Another great skyrise bar and restaurant is the Portland City Grill. They also have a great happy hour!
Where to Stay in the Portland Area
The best area of Portland to stay in is the Pearl District. While most of the city has a homeless population, mentioned above, the Pearl District is pristine, clean, and very safe. The Pearl also has public parks every few blocks and many restaurants and bars.
Residence Inn by Marriott– As a luxury traveler, I do not stay at Residence Inn’s often. The Pearl District location, however, is by far the nicest one I’ve seen. The studio room has a full kitchen, bar, living room with sectional, and spacious bathroom. The entire hotel is recently updated with modern finishes and has a very clean aesthetic. Additionally, the hotel is in a more residential area of town, where it is very safe and quiet.
Canopy by Hilton– The Canopy is a great hotel option in the Portland Pearl District. The rooms are modern and spacious, and the location is unbeatable.
The most luxurious hotels in Portland are outside of the Pearl District, therefore, expect louder street noise and more homeless. With that said, I recommend the Nines or the Duniway.
Fun Facts about Portland
- One of Portland’s slogans is “Keep Portland Weird,” and the people live up to it in the best way
- Portland has more microbreweries per capita than anywhere else in the world
- A unicycling Darth Vader, coined the Unipiper, is a city icon commonly seen on the streets
Best Time to Visit
As with the rest of the pacific northwest, Portland is notoriously gray and rainy. From October-April, you will likely have at least one rainy day. However, do not let that deter you from visiting during these months.
For the best weather, visit Portland during the summer. Temperatures will range from 70-90 degrees, and there will be little to no rain. Since summer is high season, prepare for larger crowds and higher prices.
How Long to Visit Portland Oregon
I think a long weekend in Portland Oregon is the perfect amount of time to see the city. Plan to arrive in the afternoon on Friday and leave midday on Sunday to give yourself enough time to enjoy the city without taking time off work.
If you spend more than a weekend in Portland, you can take advantage of the great day trips from the city to visit the mountains, beach, wine country, or even Seattle.
Getting to Portland
The easiest way to get to Portland is by flying directly into the Portland international airport (PDX). The airport is a quick 15-minute drive from the city and an uber will cost around $30.
If you are visiting on a road trip or live nearby, driving to Portland is another great option. Portland is 4 hours from Seattle, 7 hours from Boise, and 11 hours from San Francisco. Portland is also a great stop on a Pacific Coast Highway road trip, since it is only an 1 hour detour.
Transportation around the City
Getting around downtown Portland is easy, so I do not recommend getting a rental car unless you’re planning day trips outside the city. One option for transportation in Portland is renting a Nike bike. The electric bikes are rented from a phone app and are an affordable way to get you most places in the city.
If you prefer, there is also comprehensive public transportation with the max light rail system that goes around the city. Use the maps app on your phone for the best routes and schedule.
Walking the city is also super simple. Since the city is flat, you don’t have to worry about breaking a sweat getting places. Also, the city is built on a grid with sequential numbers in one direction and alphabetical street names in the other. This way, it is easy to gauge how far you are from your destination at any point.
Safety in Downtown Portland
While I like to focus on the positive with travel, it is important to provide a complete overview of destinations so you can make an informed decision of where to travel. While Portland is a great city, it was hit hard by 2020 and has not recovered. There is an extremely high homeless population. Most of the people are kind, but some are aggressive or even violent. There are also tents scattered all around the sidewalks and public parks.
This shouldn’t deter you from visiting but have a plan in place to stay safe. I recommend traveling in groups, and not at night. Give extra space to people that seem distressed and be always aware of your surroundings.
Summary of My Weekend in Portland Oregon Itinerary
This weekend Portland itinerary and guide will set you up for a great trip. If you are wondering exactly how to spend your time, this is what I suggest:
Friday– Arrive in Portland and enjoy dinner at Carlita’s or Grassa then cap off the night at Vault.
Saturday– Brunch at Brix followed by a brewery tour and Powell’s. End the night with dinner or happy hour at Portland City Grill.
Sunday– Breakfast at Blue Star or Voodoo then an outing to Multnomah falls.
A weekend in Portland should be full of food, beer, and relaxation. Take advantage of the laid-back atmosphere of the Pacific Northwest to break out your casual clothes and inner hipster.
Now that you know what to do, where to eat, and where to stay, enjoy your Portland weekend trip!
