Pioneer Courthouse Square, Portland: Our most recommended tours and activities

Portland: All-Inclusive Walking Food Tour

1. Portland: All-Inclusive Walking Food Tour

Explore downtown Portland on an all-inclusive walking food tour through the heart of the city. We'll meet at "Portland's Living Room," Pioneer Courthouse Square, and venture deeper into downtown while sampling food from unique vendors. Enjoy a philosophical introduction to Portland's iconic food cart ecosystem while learning about our city's history, culture, and people. On our tour we'll walk through the neighborhoods of downtown, old town, and chinatown, while passing through the largest independent bookstore in the world, our scenic waterfront park, and the famous Saturday Market (weekends only). Come hungry.

Portland, Oregon: Soul of the City Walking Tour

2. Portland, Oregon: Soul of the City Walking Tour

Discover some of Portland's most influential architecture, from cast iron-fronted structures to the grandly disastrous post-modern Portland Building, on this walking tour. Discuss the modern rise of radical activists, and how it is connected to the city’s history going back more than a century. Meet your guide in the center of the city, at Director Park, only a block from the city's Cultural District. Walk through the South Park Blocks, visiting the plazas connected to museums and concert halls, including the Portland Art Museum and the Oregon Historical Society. Explore how Portland got its nicknames and city layout, how its cultural identity was forged, and where its commitment to racial justice and social progressivism comes from. Be surprised as you find out how the state of Oregon was founded and why. Next, meet Portlandia, the image personifying the city. Learn how much of the city as you see it today has hippies to thank for its richness. End the tour at Pioneer Courthouse Square. On days when attractions are open, you can briefly enter 1 or 2 buildings. Along the way, discover what led to the prioritization of parks throughout the city center, how the city’s early urban planners decided on their layouts, how modern designers look at the past and plan for the future, and who the streets are named after.

Portland: Sightseeing Tour with Columbia Gorge Waterfalls

3. Portland: Sightseeing Tour with Columbia Gorge Waterfalls

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. This 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. 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, and the South Park Blocks. 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. Your Gorge adventure will take place along the Historic Columbia River National Scenic Byway, where some of the locations we may stop include, Portland Women’s Forum, Crown Point Vista House, Latourell Falls, Multnomah Falls, and Shepperd’s Dell. Millions of years ago, during the formation of the Cascade Mountain Range, lava and other pyroclastic matter flowed west from what would be the Cascades all the way to the Pacific Ocean, creating a thick shell of basalt rock that covered Western Oregon. Then, during the Pleistocene Ice Age, roughly 15,000 years ago, water from the Lake Missoula Flood carved out the Columbia River Gorge as hundreds of cubic miles of water, ice, rock and mud rushed from present-day Montana to the Pacific Ocean. Explore the beauty of the canyon walls and rock formations, breathtaking waterfalls and awe-inspiring visas that make the Columbia River National Scenic Area one of the Seven Wonders of Oregon. Our enthusiastic guides will introduce you to the most amazing places in the Gorge while providing a comprehensive narrative of this spectacular landscape and its transformative history.

Portland: Half Day City Sightseeing Tour

4. Portland: Half Day City Sightseeing Tour

Enjoy a fascinating and informative narration by your 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. Highlights also include a stunning stroll through the oldest International Rose Test Garden in the entire United States and a walk through the ornate grounds of the historic Pittock Mansion, built in an impressive French Renaissance nouveau style by one of Portland’s first titans of industry. Participants will enjoy sweeping views of the Portland city skyline, surrounding snow-capped volcanoes, lush evergreen forests, charming neighborhoods, dynamic downtown and myriad displays of artwork encompassing an array of vivid murals and iconic statues.

Portland: Smart Phone Scavenger Hunt

5. Portland: Smart Phone Scavenger Hunt

Turn Portland into a giant game board on a smart phone operated scavenger hunt of the city, and discover the sights from a new perspective! The interactive hunt combines all the fun of the “Amazing Race” with a sightseeing tour of some of the city’s most historic areas. Let your smart phone guide you past well-known attractions and overlooked gems, solving clues and completing challenges as you go. Start on Pioneer Courthouse Square and continue to the Arts District. See Art Deco theaters and riverside panoramas as you pass sights such as the Portland Art Museum, statue of Portlandia, Ira Keller Fountain Park, and Powells Books, flagship store of the largest independent bookstore chain in the world! The route covers approximately 2.4 miles, and lets you experience Portland’s famous street cars along the way. You can start when you want, and determine your own pace of play. Stop for lunch, take in the sights, or grab a bite at Voodoo Donuts - “the magic is in the hole!” Tours are set at a fixed price for a group versus per person pricing, so this is the perfect city adventure for groups who want to get the best bang for their buck.

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Pioneer Courthouse Square, Portland

Pioneer Courthouse Square, Portland

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Other Sightseeing Options in Pioneer Courthouse Square, Portland

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