A Weekend in Portland, Oregon

Choose Your Own Adventure

One of the Pacific Northwest’s largest cities, Portland, Oregon, is full of foodie restaurants, craft breweries, coffee, art, history, and outdoor wonders.

If you only have a weekend to explore the city, use this ‘Choose Your Own Adventure’ guide to help you plan your trip. We’ve combined some of our favorite Portland activities and sights to give you an insider glimpse into the city’s culture.

See What is the Pacific Northwest {for travelers}

Friday

Option 1 – Powells Books

The largest used and new bookstore in the world.

This wonderful land of books is excellent for everyone. Whether you are a big reader or not, you will find something to interest you here.

Option 2 – Hike or drive to Pittock Mansion

Get a great view of the city of Portland from the gardens of Pittock Mansion. This is a breathtaking view of the city lights if you go in the evening.

The grounds are beautiful in the Spring and Summer as the garden is in full bloom. Fall is a great time to view the color changes as the seasons shift.

Tour the mansion for a glimpse of the history of Portland. Check the website for openings as the hour’s change depending on the time of year.

Admission for adults is $12; for seniors, it’s $10, and youth (6-18) is $8.

Dinner

Option 1 – Pok Pok

Thai restaurant tucked away in a neighborhood of Portland.

Option 2 – Little Big Burger

Serving slider-sized burgers and truffle fries. A super simple menu, but delicious.

(Note from Cheri: across the street from Little Big Burger is the famous Salt n’Straw Ice Cream and a block up is Great Notion Brewery, with an extensive selection of craft brews, making this the perfect trifecta of gluttony!)

Saturday

Breakfast

Option 1 – The Saturday market

Visit the Saturday market and choose your breakfast from one of the many food carts available.

Option 2 – Tin Shed

A farm to table restaurant serving brunch.

Option 3 – Bowery Bagels

Bagel shop. Choose from a large variety of New York style bagels and toppings.

Coffee

Option 1 – Stumptown Coffee Roasters

Check out their website to choose from one of their locations.

This is voted Portland’s best coffee roaster.

Option 2 – Ranger

Coffee and chocolatier.

Great for a piece of specialty toast, a cup of drinking chocolate, or a designer chocolate bar. And of course a coffee of your liking.

Option 3 – Behind the Museum Cafe

Behind the Museum is located near the Portland Art Museum and the Portland Historical Society. A Japanese style cafe serving coffee and matcha’s among other tasty treats.

Saturday activities 

Option 1

Outdoor – Portland Saturday Market

A market of art, crafts, food, and imports.

Option 2

Outdoors – Go waterfall chasing in the Columbia River Gorge

A day trip from Portland, The Gorge has many waterfall attractions. If you want to hit more than one, consider stopping at the following locations. These are short hikes, approximately a mile or less to reach the waterfall.

1. Latourell Falls
2. Bridal Veil Falls
3. Multnomah Falls
4. Oneonta Falls
5. Horsetail Falls

Each of these can extend to follow a longer trail to see more waterfalls deeper within the valley if you want more hiking.

Option 3

Outdoors – Do the Four T’s Trail

Start by parking at the Oregon Zoo (there is a small fee to park at the Zoo).  From here, the Four T’s Trail begins with a walking trail through several of Portland’s parks. There are approximately four miles of walking on the trail segment.

The walking trail leads up to OHSU (Oregon Health and Science University), where there is a Tram that shuttles passengers from the University (up on a hill) into Portland below. From the Tram exit, you can buy a ticket to hop on the Trolley that runs through downtown Portland.

Ride the Trolley through Portland as long as you want, it’s hop-on/off, and makes a loop. When ready to head back to the Zoo, find a Train stop (aka. the Lightrail) purchase a ticket and ride back to the Oregon Zoo.

Lunch

Option 1 – Food cart pods

There are many different food cart pods around Portland. These are city corners, or blocks full of food carts offering cuisine from around the world.

For an up-to-date guide of all things food cart – check out Food Carts Portland

Option 2 – Tin Shed

Mentioning this place again, because of its excellent food, and the lunch menu is different from the breakfast menu.

Option 3 – Screen Door

For something unique, try this popular restaurant for breakfast, lunch, or dinner. There’s usually a wait.

Saturday afternoon activities 

Option 1

Indoors – Visit one of the Portland museums

There are many different museum options, science, history, and art.

1. Omsi (Oregon Museum of Science and Industry)
2. Portland Art Museum
3. Oregon Maritime Museum
4. Pittock Mansion
5. Oregon Historical Society

Option 2

Outdoors – Explore the shops on Alberta St. 

Alberta Street is an artsy street with many unique shops and interesting locations to visit. It’s also the home to one of the Salt n’ Straw ice cream locations.

Dinner

Option 1 – Go on a progressive dinner

We did a progressive dinner a while back, starting with appetizers at Urdaneta. Then we went to Hem 23 for dinner and wrapped the evening up with gelato from Staccato Gelato. This is a fun way to see the city as you travel from one place to the next and allows you to try out multiple restaurants rather than limiting yourself to one.

Option 2 – Mediterranean Exploration Company

This is a higher-end restaurant offering the Mediterranean and Middle Eastern dishes.

Option 3 – McMenamins Rams Head Restaurant

A pub style restaurant.

Dessert

Option 1 – Salt and Straw

A creative ice cream shop offering a variety of unique flavors.

Option 2 – Ruby Jewel

Serving ice cream. Known best for their ice cream cookie sandwiches.

Option 3 – Blue Star Donuts

A donut shop.

Sunday

Breakfast 

Option 1 – St. Honoré Boulangerie

A french style bakery and coffee shop. There are multiple locations in Portland.

Option 2 – Pine State Biscuits

Classic breakfast items.

Coffee/Tea houses

Option 1 – Tea Chai Te

A delicious smelling tea shop in the upper story of one of 23rd St old-house-turned-shop.

Order a cup of steaming tea, a mixed tea, or a bubble tea.

Option 2 – Coava Coffee Roasters

Coffee shop and coffee roaster.

Option 3 – Case Study Coffee Roasters

Coffee shop and coffee roaster.

Sunday activities 

Option 1

Indoor – Explore the shops on Mississippi Avenue

A street packed with fun shops and unique places to peruse. Stop by Paxton Gate to see a fascinating natural history display of animals, bugs, and plants. Explore the plant nursery. Stop in the art boutiques and book store.

Option 2

Outdoor – Visit one, or all, of the Portland gardens

1. Lan Su Chinese Garden
2. International Rose Test Garden
3. Portland Japanese Garden
4. Crystal Springs Rhododendron Gardens

Map of all the highlights

More resources

Planning a Trip to Oregon

A Weekend in Ashland: Choose Your Own Adventure 

A Weekend in Bend, Oregon- In Summer

A Weekend in Eugene, Oregon: Choose Your Own Adventure