Pioneer Square Tours and Activities
632 Reviews
Locally known as “Portland's Living Room,” Pioneer Courthouse Square sits at the heart of downtown and takes up an entire city block.
Pioneer Square was officially opened in 1984. Prior to that, it had been the site of a hotel (built in 1890) and later a two-story parking garage. When a new and much larger parking garage was proposed in 1969, the idea of creating a public square instead gained momentum, and was the beginning of Pioneer Square. The square takes its name from the nearby Pioneer Courthouse, built in 1875.
One side of the square is a sloped staircase, akin to theater seating and perfect for the many concerts held in the square each year. There is a local TV news station at the square, an information center for the city's public transportation system, outdoor chess tables, and a 33-foot-tall weathervane sculpture that changes at noon each day to show the following day's forecast.
Today, Pioneer Square is home to a multitude of special events throughout the year, including the annual Christmas tree lighting, plays, and concerts, as well as festivals for food, beer, and art. Particularly during the summer, the square is typically quite busy.
Daily
701 SW 6th Ave., Portland, Oregon, 97204
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Portland Sightseeing Tour Including Columbia Gorge Waterfalls
391
Experience highlights of the Portland area on this full-day sightseeing tour, including the blossoming food cart culture, diverse neighborhoods, Pioneer Courthouse Square, and the unspoiled beauty of the Columbia River Gorge. Immerse yourself in a guided tour of Portland’s fascinating history and quirky contemporary culture.
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From
$135.00
Price varies by group size
From
$135.00
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
Portland Hop-On Hop-Off Tour with Gray Line
115
Explore Portland’s diverse cityscape on this hop-on hop-off sightseeing tour. With your 1- or 2-day trolley pass, create your own adventure with 13 possible stops, including the International Rose Test Garden, Powell’s Books and the Pearl District. En route, learn about the city’s history and culture from your expert guide.
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From
$37.95
From
$37.95
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More
Portland Morning City Tour
88
Explore Portland on a 3.5-hour city sightseeing tour that travels from downtown Portland to the Pearl District to Nob Hill. Take a tour of the Pittock Mansion and see Lan Su Chinese Garden, a collaboration between Portland and sister-city Suzhou, China. Stroll through the International Rose Test Garden, located in Washington Park and boasting more than 7,000 rose plants with 550 varieties represented. Learn about the history and culture of Portland, which has been growing rapidly in recent years. Your tour includes pickup and drop-off from downtown Portland hotels.
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From
$85.00
Price varies by group size
From
$85.00
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
Portland City Portland Afternoon City Tour
70
See the best Stumptown has to offer on a small-group tour of the city's top sights and attractions. Learn about local history, culture and everyday life while exploring downtown and its surrounds. Peruse the revamped Pearl District and visit Pioneer Square. Experience what makes Portland unique with stops at the International Portland Rose Garden, Pittock Mansion and Lan Su Chinese Garden. Walk away with a better appreciation for and knowledge of Oregon's largest city.
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From
$85.00
Price varies by group size
From
$85.00
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
Hop-On Hop-Off Trolley and Columbia River Gorge Tour with Gray Line
30
Explore beautiful urban Portland and the Columbia River Gorge on this hop-on hop-off combo tour. With your 2-day sightseeing trolley pass, create your own adventure with possible stops the International Rose Test Garden, Powell’s Books and the Pearl District. Then travel aside the Lewis and Clark Trail to visit Multnomah Falls and the Bonneville Dam.
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From
$101.54
From
$101.54
Discover Portland Half-Day Small-Group City Tour
19
On this 3.5-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 22 notable bridges. Your guide will return you to your departure location at the end of the tour. Book our Explore Columbia River Gorge Half-Day Small-Group Tour as well, and receive $10 cash back.
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From
$70.00
From
$70.00
Face masks required for travelers in public areas
Face masks required for guides in public areas
Face masks provided for travelers
Learn More
Intro to Portland Small Group Walking Tour
15
Want to see a bit of Portland and get some exercise while you're at it? Try a walking tour in the center of the city. You can choose from three tours based on your interests: the first covers the city's architecture and parks, the second focuses on the arts scene, and the third is dedicated to what makes Portland weird.
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From
$25.00
From
$25.00
Regular temperature checks for staff
Paid stay-at-home policy for staff with symptoms
Contactless payments for gratuities and add-ons
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Portland, Oregon City Tour!
15
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.
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From
$59.00
From
$59.00
Hand sanitizer available to travelers and staff
Regularly sanitized high-traffic areas
Gear/equipment sanitized between use
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Portland Scavenger Hunt Adventure
1
Pay tribute to Portland’s myth-laden landmarks with a fun scavenger hunt adventure! This competition adds pizzazz to a walking tour with a friendly race through Portland to solve clues, complete challenges, and track down some of the city’s hidden gems. Don’t forget your smart phone and sleuthing sensibility! Note: Price is per individual, but each team must book together to join in the same adventure.
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From
$20.52
Price varies by group size
From
$20.52
Price varies by group size
Private- Portland City Morning Tour
Portland City Tour Overview
More than just a basic Portland city tour, our half-day Bridging Cities Tour will reveal the laid-back small city feel of these fun and thriving downtowns. Not only will you experience the best Portland sites including, International Rose Garden, Pioneer Courthouse Square, best shopping area in Portland, Tilikum Crossing, Lake Oswego, Willamette Falls, the Oregon City Municipal Elevator, and downtown Oregon City. You will learn what makes the citizens of these areas so diversified, and learn the cultural history of these unique Pacific Northwest towns & cities.
Today Portland is known as one of the world’s most environmentally conscious cities.
See why Lake Oswego community is know as one of the most affluent & trendy cities nearest Portland with a 405 acre private lake.
Oregon City is the State’s first capital and the end of the Oregon Trail where you can still see the remnants of the 1800s.
…More
From
$210.00
Price varies by group size
From
$210.00
Price varies by group size
Half-Day Private Portland City Tour
Portland City Tour Overview
More than just a basic Portland city tour, our half-day Bridging Cities Tour will reveal the laid-back small city feel of these fun and thriving downtowns. Not only will you experience the best Portland sites including, International Rose Garden, Pioneer Courthouse Square, best shopping area in Portland, Tilikum Crossing, Lake Oswego, Willamette Falls, the Oregon City Municipal Elevator, and downtown Oregon City. You will learn what makes the citizens of these areas so diversified, and learn the cultural history of these unique Pacific Northwest towns & cities.
Today Portland is known as one of the world’s most environmentally conscious cities.
See why Lake Oswego community is know as one of the most affluent & trendy cities nearest Portland with a 405 acre private lake.
Oregon City is the State’s first capital and the end of the Oregon Trail where you can still see the remnants of the 1800s.
…More
From
$210.00
Price varies by group size
From
$210.00
Price varies by group size
Face masks required for travelers in public areas
Face masks required for guides in public areas
Hand sanitizer available to travelers and staff
Learn More
Private Afternoon Bridge City Portland City Tour
More than just a basic Portland city tour, our half-day Bridge City Tour will reveal the laid-back small city feel of these fun and thriving downtowns. Not only will you experience the best Portland sites including, International Rose Garden, Pioneer Courthouse Square, the best shopping area in Portland, Tilikum Crossing, Willamette Falls, the Oregon City Municipal Elevator, and downtown Oregon City, but you will also find out what makes the citizens of this area so colorful, and learn the cultural history of these unique Pacific Northwest cities.
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. Oregon City is the state’s first capital and the end of the Oregon Trail where you can still see the remnants of the 1800s, when it was the heart of the region’s lumber, flour, wool and paper mill industries.
…More
From
$170.00
Price varies by group size
From
$170.00
Price varies by group size
Private Morning Bridge City Portland City Tour
Portland City Tour Overview
More than just a basic Portland city tour, our half-day Bridging Cities Tour will reveal the laid-back small city feel of these fun and thriving downtowns. Not only will you experience the best Portland sites including, International Rose Garden, Pioneer Courthouse Square, Tilikum Crossing, Lake Oswego, Willamette Falls, the Oregon City Municipal Elevator, and downtown Oregon City. You will learn what makes the citizens of these areas so diversified, and learn the cultural history of these unique Pacific Northwest towns & cities.
See why Lake Oswego community is know as one of the most affluent & trendy cities nearest Portland with a 405 acre private lake.
Oregon City is the State’s first capital and the end of the Oregon Trail where you can still see the remnants of the 1800s, when it was the heart of the region’s lumber and paper mill industries.
Let our informative and entertaining guides show you the best these cities have to offer.
…More
From
$170.00
Price varies by group size
From
$170.00
Price varies by group size
Private Portland Discovery Tour
On this 3.5-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 27 notable bridges. Your guide will return you to your departure location at the end of the tour.
…More
From
$390.00
per group
From
$390.00
per group
Face masks required for guides in public areas
Face masks provided for travelers
Hand sanitizer available to travelers and staff
Learn More
Portland Scavenger Hunt: Pearls of the North
Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.
…More
From
$12.31
From
$12.31
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