Top Portland Historical Tours - page 2

Travel through four of Portland’s quadrants, and explore 8 to 10 of the city’s unique districts by foot and our European-style streetcar. Stroll, taste, see and learn about what makes Portland so special, with accompaniment of a passionate local, and 2.5–4 miles of slow-paced walking (4–7 km). Starting at Director Park at the edge of the Cultural District in Portland, we will begin our exploration with short streetcar segments interspersed by leisurely walks through several districts. Learn about the Art Museum, visit the Pearl District, explore the historically industrial Slabtown. See the mural district and the space-age buildings in the South Waterfront and into the University District. Walk park blocks and fountains that made the name for Portland’s urban planning, and also brought us into conflict over racial and cultural ideals. Explore how Portland’s activist spirit has challenged its government and structures, before returning you to the center of the city, Pioneer Square.

Upon arriving in Portland International Airport, avoid lugging around your baggage and waiting in line for a taxi. Book this private airport transfer and get to your destination quickly and in comfort. Transfer is available to your hotel in Portland, Beaverton, Lake Oswago, or Tigard.

Get out of the big city and explore the stunning beaches and beautiful towns along Oregon’s northern coast on this full-day, small-group tour from Portland. Visit the charming towns of Manzanita and Cannon Beach—home of the famous Haystack Rock—browse antique shops and art galleries, and stop at several beaches to maximize your time at the Oregon Coast.

Beneath Portland's vibrant streets lies a darker story. Join The Dark Below and explore the city's most chilling legends, notorious crimes, and haunted landmarks. Journey through historic Old Town and Chinatown as your guide uncovers tales of Shanghaiing, underground tunnels, tragic deaths, unsolved mysteries, and the restless spirits said to linger where Portland's darkest history unfolded. Visit iconic locations including the Shanghai Tunnel district, Old Town Pizza & Brewing, the Roseland Theater, Kells Irish Pub, and the waterfront where kidnapped sailors were once forced aboard ships bound for distant ports. Along the way, discover stories of vice, disappearances, and paranormal encounters that helped shape Portland's haunted reputation. Combining authentic local history, true crime, and ghost lore, The Dark Below offers an unforgettable journey into the shadows of one of the Pacific Northwest's most haunted cities. Guests must be at least 16 years old to participate.

Explore Oregon’s rocky northern coastline, dotted with beaches and sea cliffs, on a scenic full-day trip from Portland. Travel the picturesque US Highway 101 through quaint beach towns, stopping in Cannon Beach, Ecola State Park, and Oswald West State Park. Enjoy panoramic coastal views, geological wonders, and wind-swept beaches without the hassle of self-driving, and learn more from your guide than you would going alone.

Oregon’s Willamette Valley is known for its fantastic wine, and while it’s easy to get to from Portland by car, driving yourself means limiting your consumption. This small-group tours includes the services of a driver so you can taste wine without worrying about designating a driver, showcasing off-the-beaten-path wineries that you might otherwise miss.

Immerse yourself in the beauty and bounty of Willamette Valley's renowned wine country on this full-day, small-group tour from Portland. Perfect for all levels of wine enthusiasts—from newcomers to connoisseurs—this tour whisks you to three or four top-rated vineyards. Sample a range of varietals (tasting fees own expense), enjoy a picnic lunch, and benefit from door-to-door service.

Solve a self-guided walking quest through Ladd's Addition, Portland's hidden architectural gem in the Southeast. Decode classic ciphers, hunt for landmarks, and explore a maze-like neighborhood with diagonal streets, five rose gardens, and over 100 historic homes. Use Questo app on your phone to follow 15 stops through Ladd's Addition: Seven Corners, Ladd Circle, the historic Hat Museum house, the East and West Rose Gardens, and hidden alleys. Solve riddles, decode A-to-Z ciphers, and find architectural details most visitors miss. Each chapter has its own puzzle and a real piece of Portland history, from the 1891 diagonal street plan to the bungalow and Craftsman homes that define Southeast Portland. Start anytime, pause whenever, and pick up where you left off. Bike-friendly: works on two wheels too. Perfect for architecture fans, repeat Portland visitors looking off the beaten path, families with curious kids, or anyone who wants to keep Portland weird.

This day trip is a tour along a section of rugged coastline along Oregon's northern coast. There will be one or two town stops, and multiple stops at headlands and beaches. The trip will include a short hike through oldgrowth Sitka spruce forest, beach time, tide pools (if tides allow), sea stacks, viewpoint stops, and a lunch stop in a charming coastal town. If group interest allows, stops with a more technological history focus may be made, such as the Tillamook Air Museum and/or Tillamook Cheese Factory.

Get an insider's view of the Columbia River Gorge on this private tour from Portland. You'll take in fantastic views, visit the historic Vista House, and see Latourell Falls and the most famous waterfall of them all: Multnomah Falls. Your driver will pick you up at your hotel so that you can avoid the hassle of renting a car or obtaining vehicle permits.

Taking this 1.5 mile (2.4 km) walk through the heart of downtown Portland with a local, experienced guide offers an exploration into the city's rich tapestry of history, culture, and innovation. Portland, noted for its quirk and progressive ideals, unfolds its stories through a series of iconic landmarks, bustling public squares, and artistic expressions that color its streets. Your guide will reveal Portland's past through the emerging landscape. Depending on your guide, your path may vary. Peak Tours is licensed and insured, local and family-owned, reliable and knowledgeable. We'd love to show you around!

Discover the ultimate family-friendly adventure in Oregon, blending aviation history, breathtaking landscapes, and hands-on farm experiences. Begin at the Evergreen Aviation & Space Museum, home to the impressive Spruce Goose and a remarkable collection of aircraft. Enjoy a scenic drive through the picturesque Willamette Valley before reaching Abbey Road Farm, where adults can indulge in wine tastings while children interact with friendly farm animals like alpacas and goats. This is the perfect balance of culture, nature, and family time near Portland. - Visit the Evergreen Aviation & Space Museum and see the Spruce Goose - Enjoy a scenic drive through the stunning Willamette Valley - Experience interactive farm fun at Abbey Road Farm with friendly animals - Perfect for families looking for a mix of culture, nature, and leisure *This private tour requires a minimum of 2 participants to operate.

Visit the northwestern Oregon Coast without renting a car by booking this small-group tour from Portland. Your local guide will be on hand to provide commentary as you make your way along the Pacific Coast, and can help you and the other members of the group decide on what stops you want to make along the way.

Take in the sights of the Oregon Coast without worrying about driving with this private tour from Portland, Your driver will pick you up at your accommodations and take you west to the coast, known for its unusual mix of forest and sandy beaches. You'll get plenty of chances to stop along the way at some of the region's prettiest viewpoints and cutest towns.

Come join our tour to learn about the history of the Japanese American community in Portland and how it has helped shape the unique culture of our city! This 1.2-mile walking tour through Waterfront Park and parts of NW Portland’s historic Japantown explores the history of the Japanese immigration to the region, the unjust incarceration of Japanese Americans during World War II, and present-day cultural ties between Portland and Japan.

The Columbia River Gorge is incredibly popular, and travelers who come during the summer season must apply for entry permits well in advance. Even in the off-season, finding parking can be a challenge, but you won’t need to worry about any of that if you opt for a tour instead. This tour includes stops at Multnomah and Latourell Falls and at the Vista House viewpoint.

See the highlights of Portland in just half a day on this private tour of Portland. You'll explore downtown Portland and the nearby NW 23rd shopping district, take in city views from the International Rose Test Garden and stroll through Lan Su Chinese Garden. If you come on a Saturday, you’ll visit the PSU Farmer’s Market.

This tour goes above and beyond your average city tour. Accompanied by an expert local guide who has deep insight into the history and culture of each district, this tour of Portland allows guests to stop at iconic Portland destinations and venture off the beaten path to discover exciting hidden gems of the city.

Step into the shadows of Portland's past on a journey through the city's most haunted and historic locations. Explore the streets of Old Town and Chinatown as your guide uncovers tales of restless spirits, unsolved mysteries, true crime, and the dark history hidden beneath the modern city. Stand along the waterfront where victims of the infamous Shanghaiing trade were once forced aboard ships bound for distant shores. Visit haunted landmarks including Kells Irish Restaurant & Pub, the Roseland Theater, and Old Town Pizza & Brewing, where reports of apparitions, phantom voices, and unexplained encounters continue to this day. Discover how Portland's underground tunnel network helped shape the city's haunted reputation. This family-friendly walking tour blends authentic history with chilling ghost stories, offering an unforgettable evening of mystery, hauntings, and local legends.

Learn about Portland's history as you explore the city with a guide on this small-group tour. You'll meet your guide downtown and head up to the historic Pittock Mansion to take in the views. You'll then continue to the International Rose Test Gardens in Washington Park before heading back downtown to check out the cityscape and sample donuts.

Explore the eerie side of Old Town with this haunted pub tour in Portland. Learn about some of the city's scary history as you walk through 19th-century buildings. Sample local beers as you hear about Portland's era of kidnapping, gangs, prostitution and opium dens.

Portland is home to a buzzing array of neighborhoods, historical highlights, and natural attractions—and this private, half-day tour makes for a seamless introduction. Pick between morning and afternoon tour times and hop aboard your luxury, air-conditioned vehicle. You’ll visit the International Rose Test Garden and Pittock Mansion, and will drive past landmarks like the Oregon Zoo, Portland Art Museum, and more as you explore the city’s neighborhoods.

Discover the highlights of Portland by solving challenges and unlocking stories on your phone. Play the engaging exploration game, taking the role of an Irish treasure hunter notorious for tracking down leprechaun gold on the Emerald Isle. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Up for a fun challenge? Highlights include: • Explore Benson Bubbler, Portlandia, Gates of Old Portland Hotel, and more lesser-known places. • Enjoy a uniquely crafted story brought to you by our top-notch writers. • Learn about the fascinating Portlandia, the Statue of Liberty's trident-wielding sister. • Try a new type of experience, the perfect mix between a tour, outdoor escape game, and treasure hunt. After your booking, you will receive an email with instructions on how to download and play the game on your phone. We recommend that each user purchases a ticket for an optimal experience, although several people can share a phone.

Visit Mount Hood and Oregon's most celebrated waterfall on this private experience from Portland. Let an expert plan all the logistics and start with a drive out to Multnomah Falls in the Columbia River Gorge, before heading to Hood River for lunch, shopping, and a drive through the “Fruit Loop” agricultural region. Before heading back to Portland, get the chance to stop at Timberline Lodge at Mount Hood.