Oregon
Urban Exploration

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Our most recommended Oregon Urban Exploration

Portland: 2.5 Hour Dinner Cruise Through Downtown

1. Portland: 2.5 Hour Dinner Cruise Through Downtown

Hop onboard the vessel and be escorted to your private table. Start off with some freshly baked bread and a house salad, followed by your choice of entrée (poultry, beef, seafood, or vegetarian), and a dessert. After dinner, head out onto the observation deck to admire the city’s skyline lit up at night. Cruise along the scenic Willamette River, then pass by the impressive Steel Bridge. Along the way, learn about the landmarks from the onboard narration. 

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Portland: Downtown Ghost Tour

2. 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.

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Portland: Eastside Craft Brewery Walking Tour

3. 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.

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Portland: Underground Donut Tour

4. 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.

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Portland: Food Carts of the Eastside Bike Tour

5. Portland: Food Carts of the Eastside Bike Tour

Meet your tour guide in the thriving industrial district, where you'll be fitted for a bike and helmet before heading out on a culinary experience through some of the more than 60 food cart pods in Portland. Sample favorites spanning a range from Oregon farm-to-table delights, to snacks appropriate for late-night cravings. As you set out, your guide will learn about your food preferences and you will visit the first permanent food cart pod, anywhere. Take a neighborhood ride of between 8-12 miles (13-19 km) to three more favorite food cart pods. Learn about the fascinating tale of how Portland came to be the epicenter of the food cart craze. Bike up a gentle hill to the Hawthorne neighborhood, part of Portland's hometown story and the heart of all that's delicious, funky, and hippie. Delve into the city's foodie history, dating back to the early 1900s, and stop at a special coffee food cart made in a unique vehicle to savor a caffeinated beverage. Your guide will select food for the group to sample at each pod, including samples from carts that were favorites as the scene was being established, and others that have come more recently to be major characters in the Portland food scene. Each dish will tell a little bit more of the food cart story. You'll have the option to purchase beer or dessert before the group starts the ride back to the meeting point; a downhill coast to allow full stomachs to settle. Once back, you will be offered a map of the carts visited during the ride, and others to try beyond.

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Portland: Heart of Portland Sightseeing Cruise

6. Portland: Heart of Portland Sightseeing Cruise

Board the Portland Spirit and embark on a tour of Portland from an entirely new perspective. Learn about the area from the captain's narration. Peruse all three levels, sit indoors in the climate-controlled area or outside in the open air. Take in the views of the Portland waterfront with an available full-service bar and bistro menu available for purchase. The cruise will head south on the Willamette river to Milwaukie and north to the Steel Bridge before bringing you back to the dock.

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Discover Portland: Half-Day Small Group City Tour

7. Discover Portland: Half-Day Small Group City Tour

Take a 3-hour guided tour of Portland in a small group of no more than 11. Throughout the tour, you'll enjoy beautiful vistas as you drive the hills and bridges in a comfortable, climate-controlled vehicle. Your interpretive guide will give you background on the landmarks you pass and teach you the city's history as you wander the neighborhoods of central Portland. Make a stop at the International Rose Test Garden, where you'll have 20 minutes to walk among the 550 rose varieties. Then, you'll ascend even higher into the hills to Pittock Mansion, which provides the best view of Portland and 5 stratovolcanoes, if the weather is clear. As you navigate the city, you'll be able to take in views of the parks, gardens, bridges, and trees of this lush city.

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Bike Portland: Bridges, Neighborhoods, Poetry, and Roses

8. Bike Portland: Bridges, Neighborhoods, Poetry, and Roses

Enjoy more time riding, with occasional stops for gardens, one-of-a-kind markets, art collectives, sculptures, bridge viewpoints, and river beaches. This tour begins in the inner Eastside neighborhoods, where you will be fitted for an easy-to-ride bike and helmet, ready for a low-key 7-10 mile ride (12-16 kilometers). Your guide will lead your group into the southeast Portland neighborhood of Ladd's Addition where you’ll visit several of the city's quadrants, ride over two bridges, and along the Willamette River. You will visit semi-secret beaches, examine unique modes of transportation, see public art of every shape, color, and texture. This ride is both like a poem and filled with poetry: you will read poetry written on murals, on sidewalks, and carved into rocks. Along the tour, you will have the opportunity to photograph and explore public art, poetry, parks and beaches; and learn about all of the modes of Portland's transportation up close.

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Portland: Cannabis Culture Guided Bike Tour

9. 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.”

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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. 

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Other Sightseeing Options in Oregon

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What people are saying about Oregon

Overall rating

4.8 / 5

based on 6 reviews

This was the MOST fun and fascinating tour! we only had a few days and this was the best view and experience. So glad we did it early so we could revisit cool restaurants and places to go. Not being regular riders we were a bit concerned, but totally unfounded - the ride was easy, Portland drivers were very safe and courteous, and the stops were excellent, all so amazing!

Tour started on time. Meeting point was centrally located. Tour took us all over Portland and pointed out all the various sites as well as historical info. about the city.

Jeri was amazing!! We had the best time and really got to try a huge selection of Portland’s finest brews. Highly recommend!

Jeri was the perfect guide! Very enjoyable ride and learned a lot about Portland and its history.

It's fun. Slow cruise and good food, pianist also plays some fun songs.