How To Spend 3 Days in Portland, Oregon: A Detailed Travel Guide

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Portland, Oregon. Funky, weird, arty, green, incredible food, eclectic neighborhoods – everything you have heard about Portland is true. I have visited Portland several times now and the more I see, the more I love about this quirky city.

I recently visited to buy a car after my little van finally died (RIP Casper!). It was an unexpected visit but I definitely made the most of it, ticking some more donut shops, restaurants, and cute neighborhoods off my Portland bucket list.

I am no expert and I haven’t lived in Portland but I have visited enough places now over four visits that I feel like I can put together a pretty good three-day itinerary.

There aren’t a ton of tourist attractions in the city so this itinerary focuses on the things I enjoy when visiting Portland including trying different restaurants, visiting local neighborhoods, hiking, and drinking craft beer. To me, Portland does all of these things really well. As well as donuts.

If you have similar interests, I hope this helps you plan your own 3 days in Portland!

How To Spend 3 Days in Portland, Oregon

3 Days in Portland Itinerary – Day One

Hoyt Arboretum, Japanese Garden, Rose Test Garden, Pearl District, Willamette River Walk, SE Portland

Breakfast From Stumptown Coffee Roasters

Today is going to be a busy one so start the day off right by grabbing a coffee and pastry or breakfast sandwich from Portland’s most iconic coffee roaster – Stumptown.

Hike in Hoyt Arboretum

After fueling up, head to peaceful Hoyt Arboretum to hike a trail. I highly recommend hiking some of the Wildwood Trail to the Redwood Observation Deck. It’s a beautiful spot surrounded by large Redwood trees. If you are into bamboo groves, check out the nearby Bamboo Garden as well.

Visit the Japanese Garden and International Rose Test Garden

Right next to the Arboretum is the Portland Japanese Garden, one of the most authentic and beautiful Japenese-style gardens outside of Japan. Set over 12 acres, there are eight different types of gardens and a Japanese Tea House.

The International Rose Test Garden is also close by and it’s definitely worth stopping by for the fragrant and colorful roses here – there are over 10,000! It is over 100 years old and free to enter.

Explore the Pearl District

The Pearl District in downtown Portland is home to restored brick warehouses that house funky boutiques and gift shops, excellent cafes and restaurants, and lively bars. Don’t miss visiting Powell’s City of Books, the largest used and new bookstore in the world spread over a full city block!

Grab lunch at Pine Street Market food court in neighboring Old Town, you can find ramen, dumplings, Thai, and Costa Rican comfort food among other delicious options. Make sure to make room for dessert from either Lil’ Funky Donuts in the market or at iconic Voodoo Doughnut around the corner.

Walk some of the Waterfront Park trail along the river after lunch if you still have some energy.

Go Brewery Hopping

It’s time to sample one of the many things that Portland does so well – craft beer. There are a few excellent breweries in the downtown/Pearl District area, including Backwoods Brewing Company, 10 Barrel Brewing, Deschutes Brewery Public House, and the LOTR-themed Treebeerd’s Taphouse.

There are also a couple of great breweries in East Portland where you are going for dinner – Living Häus Beer Company and Rogue Eastside Pub and Pilot Brewery.

Visit a Giant Troll

If you want to see something really special that is only a 15-minute drive from downtown Portland, I highly recommend you visit Ole Bolle, one of six NW trolls created and built by the Danish artist, Thomas Dambo.

Ole Bolle is the only NW troll I haven’t visited, but I definitely plan to because I love these trolls! You can visit Ole Bolle for free and there is a short (0.25-mile) trail to reach him. Below is a picture of my favorite troll, Oscar the Bird King, on Vashon Island in Washington to give you an idea of what to expect.

Dinner at Kachka in East Portland

Walk over the bridge to East Portland for dinner at Kachka, a highly esteemed restaurant in the Portland dining scene that serves dishes from former Soviet Union countries as well as a selection of house-infused vodkas.

3 Days in Portland Itinerary – Day Two

Boise Neighborhood, Mount Tabor Park, Hawthorne District, Kerns Neighborhood

Explore Mississippi Avenue in Boise Neighborhood

You will start the day today in one of my favorite Portland neighborhoods – Boise. Start with brunch at Broder Nord – a Nordic brunch and lunch restaurant.

Check out the eclectic stores and boutiques along vibrant Mississippi Avenue after brunch. Don’t miss Flutter for home decor and jewelry, Mississippi Records for vinyl, PDXCHANGE for tasteful gifts and local art, and Pistils Nursery if you are a plant lover.

Hike at Mount Tabor Park

After exploring Boise Neighborhood, it’s time for a hike in Mount Tabor Park, a large forested park with an extinct volcanic cone, reservoirs, and excellent city views.

Lunch and Explore Hawthorne District

Make your way down the road to Hawthorne District where you can grab a late lunch at Hawthorne Asylum food cart pod on the site of a 19th-century asylum. There are over 20 food carts to choose from so there is something for everyone. Iconic Cartopia food cart pod is another great lunch destination in Hawthorne.

Once you have eaten, explore the shops along SE Hawthorne Boulevard. The Hawthorne District is known for its boho vibe and there are a large number of eclectic gift shops, vintage boutiques, bookstores, restaurants, and bars between 11th and 51st streets.

There are also some great breweries in Hawthorne including Away Days Brewing Co., Gigantic Brewing, and TPK Brewing Co.

Dinner at Ken’s Artisan Pizza in Kerns Neighborhood

To close out the day you will be trying some of the best pizza in Portland in one of the city’s prettiest neighborhoods, Kerns. After a delicious pizza dinner, walk north along NE 28th Avenue to check out the cute shops and boutiques.

3 Days in Portland Itinerary – Day Three

NW Portland, Forest Park, Pittock Mansion, Wonderwood Springs, Alberta Arts District

Explore NW Portland

Start your last day in Portland with a delicious biscuit sandwich or biscuits and gravy from Pine State Biscuits in NW Portland. After breakfast, explore NW Portland along NW 23rd Avenue which is one of the premier shopping streets in Portland.

For something a little different and keeping with the Keep Portland Weird mentality, check out the Freakybuttrue Peculiarium and Museum, which is part interactive wacky art gallery and part museum. It’s not recommended for children because some of the exhibits are quite creepy.

Hike at Forest Park

Get back into nature at Forest Park, a 5,200-acre forested park that is one of the largest urban forests in the country. I did the Forest Park Ridge Trail to a scenic viewpoint over the photogenic St. John’s Bridge and it was peaceful and beautiful.

Another popular short hike in Forest Park is to the Witch’s Castle, an old stone restroom in the forest that is covered in moss and graffiti.

Tour Pittock Mansion

If you enjoy visiting historic house museums, then you should add Pittock Mansion to your itinerary. The mansion is a 23-room French Renaissance-style home that is over 100 years old and has been beautifully preserved. You can take a self-guided tour and find out what life was like for the well-to-do in Portland a century ago.

Lunch at Quirky Wonderwood Springs

Drive over the majestic St. Johns suspension bridge to Wonderwood Springs in St Johns, a unique fantasy wonderland that has themed drinks, a restaurant, and mini golf. Grab a late lunch here or at one of the other restaurants in St Johns.

Explore Alberta Arts District

Head over to the Alberta Arts District next, another effortlessly cool and quirky neighborhood in Portland. The Alberta Arts District is home to colorful murals, independent stores and boutiques, and cool restaurants and bars.

It’s also another great neighborhood for breweries if you want to try more of Portland’s excellent craft beer. Baerlic Brewing, Great Notion Brewing, and Conscious Sedation Beer Garden are all highly-rated local breweries.

Dinner at Hat Yai

For your last meal in Portland, head a little north of the Alberta Arts District to the lauded Thai restaurant, Hat Yai. Hat Yai is known for its out-of-this-world fried chicken but I really loved the mushroom skewers and the roti here too. Make sure to save room for dessert – you can’t pass up the delicious mango sticky rice.

And that’s a wrap on 3 days in Portland!

Where To Stay in Portland

Portland has so many great choices for accommodation no matter your budget.

For budget travelers, stay at Northwest Portland Hostel which has dorms and private rooms and is centrally located to downtown and the Pearl District. The Society Hotel is another great downtown option with dorms and privates.

Solid midrange options include the classy and well-appointed The Paramount Hotel downtown, the colorful and cozy The Inn at Northrup Station in the Pearl District, and the artistic and refined Hotel Lucia downtown.

For something a bit more luxurious, stay at The Mark Spencer Hotel – a boutique hotel in the Pearl District, or stay in your own tiny house at Tiny Digs – Hotel of Tiny Houses in the Kerns neighborhood.

My top picks for highly rated and affordable vacation rentals in cool neighborhoods are:

This article is now featured on https://www.gpsmycity.com. To download this article for offline reading or create a self-guided walking tour to visit the attractions highlighted in this article, go to Walking Tours in Portland https://www.gpsmycity.com/gps-tour-guides/portland-602.html

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June 13, 2025 by theworldonmynecklace | 0 comments

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