Portland, Oregon
Sightseeing Walking Tours

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Our most recommended Portland, Oregon Sightseeing Walking Tours

Portland: Downtown Ghost Tour

1. Portland: Downtown Ghost Tour

Take a historic and memorable look at the haunted past of Portland, Oregon, with a 1-hour walking tour. Set off on an adventure through downtown Portland with a knowledgeable and experienced guide, and discover the most haunted locations in the area. Make your way to the meeting point at Lan Su Chinese Garden and look out for your guide, who will be carrying a lantern. Begin immediately with the obscure history of the City of Roses before embarking on a haunted route to 8 locations in the surrounding downtown area. Head to the waterfront, then walk the dark streets to the Old Town Pizza to hear researched stories and eyewitness accounts of personal hauntings in Portland's morbid and mysterious past. From there, the tour only gets spookier as you visit The Shanghai Tunnels to see a firsthand reminder of Portland’s shady past where men were kidnapped or “Shanghaied” and sold to ship's captains in need of sailors, and women were captured and forced into illicit work. Learn about an entire network of vice and illicit trade that began to use these tunnels for gambling, opium dens, prostitution, and kidnapping. Your guide will then choose from some of the other most haunted locations and take you to them to deliver, in gripping detail, the history and eyewitness accounts of hauntings and paranormal activity. Finally, make your way back to the final stop at Lan Su Chinese Garden, where your guide can give you a final recap of Portland's strange activity, answer any ghost questions you might have, and check out and exchange any paranormal pictures and activity caught on camera.

Portland: Underground Donut Tour

2. Portland: Underground Donut Tour

Accompany your passionate foodie guide to 4 donut institutions, where you'll enjoy a curated sample of Portland's best donuts. Savor classics like glazed and chocolate, and discover some more adventurous flavors, like lavender.  Your stops may include Sesame Donuts, Blue Star Donuts, NOLA Doughnuts, and Voodoo Doughnuts, all true donut institutions. You'll even be able to skip the line at Voodoo Doughnuts, where some people wait up to 30 minutes. On the way to the donut shops, visit some local sights including Pioneer Square, Chinatown, and the PSU Campus. Your tour guide will entertain you with interesting facts about these sites as you travel between treats.

From Portland: Willamette Valley Character Wineries

3. From Portland: Willamette Valley Character Wineries

Meander the wine appellations of the Willamette Valley, and discover vineyards and tasting rooms that stand out, not only for the views and the character of their wine, but the intriguing personalities (both human and non-human) involved. You and your small group will learn background on the history, terroir, and character of Willamette Valley wine from your interpretive guide. This day trip is a customized tour of 3-4 wineries in the Willamette Valley. You’ll travel south and west of Portland, as your guide takes you through the farmland of the Willamette Valley, one of the richest valleys in the world, known for its hazelnuts, berries, Christmas trees, and Pinot Noir. You may stop at a farm stand to get farm-fresh eggs or fruits, nuts, & vegetables.  You'll be served a lunch platter at the second winery, accounting for your dietary needs. You'll wander through the rolling hills of multiple Willamette Valley sub-AVAs, passing through charming little villages, while making stops at some of the most unique boutique wineries. Afterwards, you’ll head back to Portland to be dropped off at your hotel.

Portland: City Highlights Exploration Game

4. Portland: City Highlights Exploration Game

Your adventure starts at City Hall in downtown Portland. Begin your first adventure in the app and successfully complete the challenges to unlock more whacky stories and discover more locations. Unlock stories about the Shanghai Tunnels, through which unsuspecting visitors were kidnapped and carried to sea, or the Portland Hotel, where dismembered bodies were dumped. Uncover Skidmore Fountain, which would’ve run with beer instead of water if civic leaders had a sense of fun. In another story, you embark on an adventure to the leprechaun colony in Mill Ends Park from which a pot of gold has been stolen by Portland’s famous peregrine falcons. As an Irish treasure hunter, it’s your job to track it down.

Portland: Food Carts, Pods, & Patios Tour

5. Portland: Food Carts, Pods, & Patios Tour

Discover what the food cart hype is all about in the city that put food cart pods on the map. With over 700 food carts throughout the city, your guide has done the research for you. Visit several locally run and operated food carts, relax on patios in the heart of Southeast Portland, and taste the delicious foods that make Portland a true foodie destination. On this small-group walking tour, discover global foods, quench your thirst with tasty drinks, and learn fun history in this off-the-beaten-path neighborhood. Experience the perfect way to discover quirky Portland, eat where the locals eat, and have fun.

Portland: Eastside Craft Brewery Walking Tour

6. Portland: Eastside Craft Brewery Walking Tour

Meet your guide and small group across the river from downtown Portland in the inner Eastside industrial district. The meeting point on SE 7th Avenue is located in the heart of so many scenes, from coffee to food, distilleries and street art. For the best of Portland's brewery innovation and history, start here, where beer (and cider) flourish and learn of Portland's craft brewing history from those who lead the way.  Walk into the hotbed of beer, through the neighborhood that borders the Willamette River and allow your guide to personally select breweries representing a trip through the Oregon's brew past, present and future⁠—and the whole US. Follow your guide through the Eastside, where you'll find an assortment of beers to satisfy your personal preferences, like sours, craft barrel-aging, Belgians, wits, imperial IPAs, and more.  Walking distance will be 2-3 miles (3-5 kilometers), with just enough beer tasting so you'll know which stop you'd like to return to. At each brewery, your guide will lead you through the choices and let you select your favorites, offering you recommendations for a classic experience, or customized the tasting to fit your likes and dislikes. Cider options are available at each brewery for gluten-free or wheat-free tour guests, and the route is mostly flat so the walk is appropriate for all abilities. This craft brewery walking tour is conversational in style; your guide is eager to share beer knowledge as well as a window into the culture of this neighborhood, one which has supported the city's street artists, skateboarders, brewmasters, food innovators, and a number of other unique parts of the city's evolution from an afterthought to a sought-after destination for tourists worldwide.

Portland: Columbia Gorge Waterfalls 40-Minute Scenic Flight

7. Portland: Columbia Gorge Waterfalls 40-Minute Scenic Flight

Embark on a scenic flight through Oregon's pride and joy, the Columbia River Gorge. On this 40-minute flight, get a bird's-eye view of Multnomah Falls as it cascades down 2 drops equalling 620 feet. Listen as your expert pilot and guide narrates the experience.  Learn about the steps taken by Oregon's forestry service to bring the Gorge and it's natural waterfalls back to life in the wake of Oregon's 2017 Gorge fire. Despite the intense burning, the beauty of the Gorge remained and the force of the waterfalls persisted. With some of the hillsides and ridges all but destroyed, the stubbornness of nature is clear as you fly above thousands of acres of trees, seemingly untouched by the heat and fury of the flames. Soar by the Bridge of the Gods, the link for Pacific Crest Trail (PCT) hikers to cross between Oregon and Washington, before making a turn back to your starting point. Land back at the meeting point and disembark with a collection of unforgettable impressions.

Portland: Cannabis Culture Guided Bike Tour

8. Portland: Cannabis Culture Guided Bike Tour

Meet your guide at the local operator’s bike store in one of Portland’s uniquely funky neighborhoods then head out onto the city streets where your cannabis adventure awaits. On the tour, learn about how Oregon has been a forerunner in cannabis legalization since the 1970s as you take part in a 14.5 km bike ride through the city, visiting dispensaries, head shops, and local hot spots along the way. The experience introduces you to the history of Portland as it influences, and has been impacted by, the story of hemp and cannabis, from the 1800s to the present. Visit two hand-picked dispensaries where you’ll learn what the differences are between strains like sativa, indica, and hybrids, as well as why the aroma of marijuana buds can be a clue to what might be best for you. Enjoy the opportunity to shop for cannabis and edibles, or just learn more about Oregon’s finest farms and strains. Next, wander through the world of art glass and see the spectrum of glass art from purely functional to true works of artistic genius (but still smokable). You can also shop for stunningly crafted wooden pipes, then if you’ve got the munchies, explore the best choices for late-night (or late-afternoon) cravings. In just three hours, experience Portland’s culture and history, and shop for cannabis more confidently, along with a beautiful ride through the city’s neighborhoods that locals call “hippie central.”

Portland: "Keep Portland Weird" App-Guided Tour

9. Portland: "Keep Portland Weird" App-Guided Tour

Discover the local breweries, cafes, parks, art, and quirky neighborhoods of Portland on this app-guided tour. With a focus on individuality, creativity, and innovation, Portland is a great place to explore. During this "Keep Portland Weird" tour, explore the interesting history of Portland, visit a few of the most unique shops and stops, and find out the best places for food and drinks. Walk at your own pace, choose your own starting point, and listen to the tour from your mobile device whenever you want. You can choose to follow one of the suggested routes, complete with easy-to-follow directions, or walk to the stops in any order. The audio will play automatically when you arrive at a stop. Enjoy access to the tour for seven days from the first day you launch the experience. You could start one night and finish the next, it's completely up to you. No tour guides, no crowds, and no schedules to keep.

Portland: 2 Hour Family Walking Tour with Guide

10. Portland: 2 Hour Family Walking Tour with Guide

Spend a family fun day out on this guided walking tour, designed to suit all ages and interests. Meet your guide, then set off into Portland’s bustling city streets where your sightseeing adventure begins. Along the way, visit some of the city’s most iconic sights and landmarks, and learn interesting facts and stories about Portland's history. Hear how the city got its name, discover hidden secrets as you head off-the-beaten-path, and go searching for miniature horses. The tour has an easy pace, and your guide ensures the whole family has fun. 

Frequently asked questions about Portland, Oregon Sightseeing Walking Tours

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Other Sightseeing Options in Portland, Oregon

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What people are saying about Portland, Oregon

Overall rating

4.7 / 5

based on 423 reviews

Bo was a fantastic tour guide! We got a history lesson on Portland, and each of the donut shops that were on the tour. Bo made it fun and exciting for my family and I. Not only did we get to taste some amazing donuts, we got some fantastic recommendations on places to eat dinner, and other tours like ice cream and pizza. The only I would say is they need to update there website on how many stops there are. I thought it was 2, and one website said 5, but there were 4. All the places plus the nice walk around Portland was absolutely worth the money we spent.

Beau was great. Friendly and knowledgeable about Portand and donuts. He took time to learn our names and where we were from. Gave great description about all the stores and what made them famous. When we left Voo Doo to hike back to start, we didn't feel safe as we were on own. We follow directions give but some of yhe area was dicey. Guy broke out a car window in front of us just a block from Voo Doo.

It was amazing.. but I think that the description before booking should state its ALOT of walking and probably not meant for disabled persons. And bring a bag of buying doughnuts

Great tour full of valuable information and tons of recommendations for the city. Beau was really helpful about more than just donuts! Would do the tour again!

Guide was great and knowledgeable. Lots of great history and spooky stories!