Pioneer Square Tours & Attractions

Explore the essential food and drinks at the heart of downtown Portland, Oregon on this all-inclusive walking tour led by an experienced, professional, Portland-native guide and standup comedian. Meet local vendors and hear their stories while getting inside knowledge about the city, its history, its food, and its identity. This is your insider access to some of the best-known and best-hidden bites that define downtown.

This tour is operated by a small local business, and due to our lean business model and relationship to other local small businesses, we are capable of offering unrivaled value and flexibility.
Duration: 3 to 4 hours.

10 a.m., 1:30 p.m., 4 p.m.

Start at DIRECTOR PARK

Our downtown Portland, Oregon tours are engaging, well-paced and colorful: the Best of the City! It’s a weird city, but there are stories in every building, park and brick. We’ve organized our city’s best things -- and of course, its most complicated and conflicted, as well. In an ever-changing world we continuously change the story of the city.

Much of Portland’s history can be told through the buildings and street layouts including the prioritization of parks in the city center. It’s not a dry history: full of back-room deals, early deaths and greed; and then there were hippies!

How did Portland become the 1st city on the West Coast with a fine art museum? How did the city's early cultural reputation influence its mid-20th century; and how did it become such a lightning rod for racial justice protests? We'll discuss what was, is, and will be the soul of the city.

We keep groups to no more than 15 for personalization and safety.
Duration: 120 to 150 minutes.

Come explore the unique history and diverse culture of the entertainingly eccentric city of Portland! Enjoy a fascinating and informative narration by your local guide, highlighting the colorful past and present of Portland’s many historic churches, diverse modern architectural wonders, abundant city parks, bountiful boutiques and world famous culinary hot spots.
Duration: 3 to 4 hours.

More than just a basic Portland city tour, our half-day Portland City Tour will reveal the laid-back small city feel of this fun and thriving downtown. You will experience the best Portland sites including the International Rose Garden (seasonally), the World Forestry Museum (seasonally), the Oregon Society of Artists (seasonally), Pioneer Courthouse Square, NW 23rd (the best shopping area in Portland), the Pearl District, the South Park Blocks, and Lan Su Chinese Garden.

Today Portland is known as one of the world’s most environmentally conscious cities: a hub for farm-to-table eateries, alternative lifestyles, a large community of cyclists, and high walkability. Let our informative and entertaining Tour Guides show you the best the City of Portland has to offer.
Duration: 3 hours 30 minutes.

On this full-day tour, you’ll see the best of the Portland area and the Columbia River Gorge. Along the way, learn about Portland’s interesting history and modern-day culture from your guide.
Our half-day Portland City Tour will reveal the laid-back small city feel of this fun and thriving downtown. You will experience the best Portland sites including the International Rose Garden (seasonally), the World Forestry Museum (seasonally), the Oregon Society of Artists (seasonally), Pioneer Courthouse Square, NW 23rd (the best shopping area in Portland), the Pearl District, the South Park Blocks, and Lan Su Chinese Garden.
On the half-day Gorge Waterfalls tour you will explore the beauty of the canyon walls and rock formations, breathtaking waterfalls and awe-inspiring vistas that make the Columbia River National Scenic Area one of the Seven Wonders of Oregon.
Duration: 8 hours 30 minutes.

We've always had a passion for donuts, but only recently did we realize just how many others do too. And when looking around, we didn't see anything that truly celebrated donuts in all their glory, hence the Underground Donut Tour was born. This tour is for anyone who truly enjoys donuts. At each location, you'll be able to try a curated sample of one of that location's best donuts. Many locations offer vegan, gluten, or nut-free options, however, please make sure to let us know ahead of the tour, so we can make sure to highlight those specifically for you. Our tours include such favorites as Coco Donuts, Blue Star Donuts, Nola Doughnuts, Voodoo Doughnuts, and more.

We also offer much more information about the route, the city, the stops, and more.

We hope you can join us!
Duration: 2 hours.

Join Secret Food Tours through Downtown Portland, Oregon. Delight in the fusion of international flavors with locally sourced and crafted ingredients, showcasing the vibrant diversity of the city.

Immerse yourself in our city’s rich history, while capturing the essence of Portland’s food scene. You will discover local culinary gems by savoring an array of extraordinary and authentic dishes.
Duration: 3 hours 30 minutes.

On this 3-hour tour, you'll get a broad overview of the Central City. We'll make stops at Pittock Mansion and the International Rose Test Gardens. At Pittock Mansion, you'll get pictures of the best views of the city, and Mt. Hood if it's a clear day. You'll have plenty of time to smell the roses at the Rose City's most famous garden. Your expert guide will provide background on the sites and city history, while navigating through city traffic, so you don't have to. You'll meander through all of the major neighborhoods of inner Portland on both sides of the river while gaining views of 14 of Bridgetown's 29 notable bridges. Your guide will return you to your departure location at the end of the tour.
Duration: 3 hours.

More than just a basic Portland city tour, our half-day Portland City Tour will reveal the laid-back small city feel of this fun and thriving downtown. You will experience the best Portland sites including the International Rose Garden (seasonally), the World Forestry Museum (seasonally), the Oregon Society of Artists (seasonally), Pioneer Courthouse Square, NW 23rd (the best shopping area in Portland), the Pearl District, the South Park Blocks, and Lan Su Chinese Garden.

Today Portland is known as one of the world’s most environmentally conscious cities: a hub for farm-to-table eateries, alternative lifestyles, a large community of cyclists, and high walkability. Let our informative and entertaining Tour Guides show you the best the City of Portland has to offer.
Duration: 3 hours 30 minutes.

On this ALL-INCLUSIVE 3-hour tour, you'll get a broad overview of the Central City. We'll make stops at Pittock Mansion and the International Rose Test Gardens. At Pittock Mansion, you'll get pictures of the best views of the city, and the five stratovolcanoes that are visible on a clear day. You'll have plenty of time to smell the roses at the Rose City's most famous garden. Your expert guide will provide background on the sites and city history, while navigating through city traffic, so you don't have to. You'll meander through all of the major neighborhoods of inner Portland on both sides of the river while gaining views of 14 of Bridgetown's 29 notable bridges. Your guide will return you to your departure location at the end of the tour.
Duration: 3 hours.

Jumpstart your morning with a huge variety of coffee and donuts across 4-5 mouthwatering stops where each bite and sip was crafted right here in Portland. Along the way, immerse yourself in quirky history while exploring Downtown Portland. We like to think this the perfect way to discover Downtown Portland, see where locals get their coffee and donut fix, and have fun!

Tour highlights:
- Get an expert-led demonstration on the art of pour-over coffee at a cafe which uses cutting-edge technology to guarantee perfection.
- Portland has over 75 locally owned donut shops, and we’ll sample a selection of the best from our favorite.
- Stand in Pioneer Courthouse Square and learn all about “Portland’s Living Room”.
- At the coziest Portland hole-in-the-wall café, indulge in a traditional macchiato paired with a homemade French pastry.
- Plus much more!

Note: We do not visit Voodoo or Blue Star during this tour as they are on the common tourist track – instead we keep it local.
Duration: 2 hours 30 minutes.

Embarking on a 1.5 mile (2.4 km) walk through the heart of downtown Portland offers an immersive exploration into the city's rich tapestry of history, culture, and innovation.

Portland unfolds its stories through a series of iconic landmarks, bustling public squares, and artistic expressions that color its streets. You'll encounter not just the narrative of its past, but the living, breathing essence of what makes Portland beloved.

Admire vibrant murals and sculptures that punctuate the cityscape. Witness the symbiosis between architecture and environment. Even the smallest park in America claims its fame among the city's green spaces.

We'll share how Portland changed from a forest, to the wild-west "stumptown," to the vibrant "little" city it has become. This walk isn't just a physical journey but a passage through time, revealing how Portland's innovative spirit has shaped its identity from historic times to the present day.

Each tour may vary, depending on your guide.
Duration: 2 hours.

See all of Portland’s top attractions on this hop-on hop-off trolley tour, a fun, easy way to sightsee. With your 1-day or 2-day pass, explore Portland aboard a sightseeing trolley and hop off at any of the 9 stops to visit Washington Park, the Pearl District and more. Enjoy the fresh air with the open seating or opt for the indoor seating section. Your expert guide will offer commentary about the history and culture of Portland throughout your ride.
Duration: 55 minutes.

Come breakfast with us! Delve into three of Portland’s most acclaimed drinks and morsels. On this two hour tour you will experience Portland's coffee culture, our iconic artisanal donuts, and deliciously crafted chocolates. The perfect way to start any vacation in the Rose City.
Our guides will share with you Portland's history in the third wave coffee movement, while leading you on a 1.5 mile walk through Portland's downtown. Embrace fantastic donut creations in entirely new flavor combinations as you learn about the origins of the donut and how it became a Stumptown staple. Finally we will visit chocolate makers, were we will learn more about chocolate varietals and their unique flavor profiles.

Dietary restrictions: we CAN provide substitutions for vegetarians, non-alcohol guests, vegan, gluten free, or dairy allergies. All allergies and dietary restrictions must be indicated in advance at time of ticket purchase.
Duration: 3 hours.

More than just a basic Portland city tour, our half-day Portland City Tour will reveal the laid-back small city feel of this fun and thriving downtown. You will experience the best Portland sites including the International Rose Garden, Pioneer Courthouse Square, NW 23rd (the best shopping area in Portland), the Pearl District, the South Park Blocks, and Lan Su Chinese Garden

Today Portland is known as one of the world’s most environmentally conscious cities: a hub for farm-to-table eateries, alternative lifestyles, a large community of cyclists, and high walkability. Let our informative and entertaining Tour Guides show you the best the City of Portland has to offer.

Duration: 4 hours 30 minutes.

Embark on a captivating journey into the enchanting realm of Portland's Sushi scene, guided by our passionate experts. The Sushi Tour transcends boundaries, seamlessly blending cultures, cuisines, and camaraderie. It's an evening of friends coming together at the intersection of entertainment and education, where the magic of dinner unfolds.

Omakase, meaning "I'll leave it to you," becomes the guiding principle of this experience. Entrust your culinary adventure to our dedicated team of Sushi experts, in collaboration with Portland's renowned Sushi Chefs, as they curate a selection of dishes that epitomize the essence of Sushi. This sophisticated tour unfolds over 2-3 hours, covering a delightful 1-mile walk. Immerse yourself in the artistry and flavors that define the elegance of Portland's Sushi scene.
Duration: 2 to 3 hours.

Turn Portland into a giant game board with this fun scavenger hunt adventure! This challenge combines the excitement of the Amazing Race with a 3-hour city walking tour. Guided from any smart phone, teams make their way among well known and overlooked gems of the city, solving clues and completing challenges while learning local history. Note: Pricing is per individual, but teams must book together in order to be included in the same adventure. Streetcar fee is not included ($2 each)
Duration: 3 hours.

More than just a basic Portland city tour, our half-day Portland City Tour will reveal the laid-back small city feel of this fun and thriving downtown. You will experience the best Portland sites including the International Rose Garden, Pioneer Courthouse Square, NW 23rd (the best shopping area in Portland), the Pearl District, the South Park Blocks, the PSU Farmers Market (on Saturday AM tour only), and Lan Su Chinese Garden.

Today Portland is known as one of the world’s most environmentally conscious cities: a hub for farm-to-table eateries, alternative lifestyles, a large community of cyclists, and high walkability. Let our informative and entertaining Tour Guides show you the best the City of Portland has to offer.
Duration: 4 hours 30 minutes.

Our smartphone-guided tour brings the facts and stories behind Portland to life because we've taken the same stops and sights we share with our friends and families when they come to town and created an interactive web-based tour for you!

Read the stories behind the city, answer questions to reveal fun facts, and experience what makes Downtown Portland incredible! Purchase your tour and then navigate to our website to enter your access code and launch the tour. You can either start immediately or create an account and come back when you are ready to explore.

Please note that you and your group read the tour aloud - there is no audio functionality at this time.
Duration: 70 to 90 minutes.

We’re definitely Keeping It Weird on the Underground Donut Tour - Portland Holiday Edition. Come join us as we take a stroll through downtown Portland and try some of the best donuts you'll ever have in your life. Seriously, these donuts are amazing. The tour starts near the PSU campus where we try an assortment of donuts. Next, we take a leisurely walk through the park towards downtown Portland. Along the way you'll learn about Portland history, both for donuts as well as the larger restaurant industry. Depending on what's open that day, we may stop at one of several donut shops downtown, so make sure to bring your appetite. We'll stop along the way to admire the holiday lights and decorations, specifically in Pioneer Square. Lastly, we'll stop at the place that started it all, Voodoo Doughnuts. Don't worry though, because we can skip the line. Along the way, we'll sprinkle in some humor, history, and fun for the whole family. What's not to love?

We hope you can make it!
Duration: 2 hours.

Experience the most popular tour of Portland and the Columbia River Gorge available anywhere! Join us for a comprehensive introduction to the City of Portland and the Columbia Gorge National Scenic Area, which includes detailed visits, magnificent views and concise information of the area’s best attractions. The tour combines some of the most iconic and unique places in Portland with the natural beauty and splendor of the waterfalls, scenic vistas, and historical sites in the Columbia River Gorge.

Highlights:
-You will experience the best Portland sites including the International Rose Garden, Pioneer Courthouse Square, NW 23rd (the best shopping area in Portland), the Pearl District, the South Park Blocks, the PSU Farmers Market (on Saturday AM tour only), and Lan Su Chinese Garden.
-Explore the Columbia River Gorge! Site we may visit include: Portland Women’s Forum, Vista House, Latourell Falls, Bridal Veil Falls, Multnomah Falls and more.
Duration: 4 hours 30 minutes.