Top Portland Walking Tours

Intimidated by Portland’s surfeit of food trucks, restaurants, and must-try eateries? Leave all the planning to your guide—and sample brunch bites that Portland has to offer—on this small-group foodie walking tour. Meet your guide in the morning, and come with an appetite: you’ll visit numerous businesses in the Mississippi District for bites ranging from pastries and sandwiches to drinks and beyond.

Portland’s historic Mississippi District is home to killer live music venues, eclectic shops, and some of the best restaurants, bars and food carts in any city – especially if you know what to look for. On our walking food tour of Mississippi Avenue, that’s exactly what I’ll show you! Some of the delicious food and drinks we'll sample: - Perfectly cooked egg sandwiches on fresh-baked sourdough. - Locally roasted coffee or craft cocktail (or coffee cocktail!). - Mouth-watering cake & brioche donuts with seasonal ingredients. - Deliciously authentic cubanos and sweet plantains with mojitos. - Melt-in-your-mouth brisket & more from the West Coast’s #1 BBQ spot. Come hungry, thirsty, and curious! The food is the star of this tour, but you’ll also learn about historic Mississippi Ave and the city of Portland. This neighborhood is weird and wonderful, and I’ll share some of the most interesting tidbits along the way.

Explore Portland's hipster-friendly Buckman neighborhood on foot and try out some fantastic local fare along the way with this small-group walking tour. While dining options vary depending on availability, you're likely to visit some of Portland's top international restaurants, try out treats from a food pod, and spend time at a local distillery, all with a guide to provide context and narration.

Visit the Columbia Gorge, easily one of Oregon's most scenic spots, with this intimate half-day tour from Portland. You'll make plenty of stops along the way, with the chance to take in the views from the aptly named Vista House and the Portland Women's Forum State Scenic Viewpoint. You'll also visit Horsetail Falls, Latourell Falls, and the most famous waterfall of them all, Multnomah Falls, the tallest waterfall in the state.

A vivid walk through Portland's rough-and-rowdy beginnings. Follow the Willamette from docks to depots, uncovering how river trade, lumber wealth, railroads, immigration, and vice built the city between 1845 and the early 1900s. Expect steamships, saloons, Shanghaiing legends, and plenty of frontier swagger. Solve puzzles, explore the city, and find hidden gems at your own pace. Try a new type of experience with your smartphone, the perfect mix between a walking tour, sightseeing, and a scavenger hunt.

Discover lava tube caves, old-growth forests, waterfalls, and more on a guided tour of Mt. St. Helens. The park’s vastness and variety of attractions can be overwhelming on your own, but by visiting with a guide you don’t miss any of the highlights. Plus, you can learn about the area’s geology, ecology, and history—much of which you might miss if visiting the park on your own.

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.

Step off the beaten track and discover the real engine behind Portland's eccentric reputation. This self-guided walking tour explores haunted Victorian coffeehouses, radial garden labyrinths, inclusive zine shops, reclaimed cemetery grounds, thrift collectives, painted street intersections, and community-saved film archives. Led by sociologist Lukas and local detail expert Olivia, you will uncover how grassroots activists, independent business owners, and creative visionaries fought to keep the Rose City stubbornly unique against corporate homogenization. - A 7.8 km self-guided tour with 8 stops and 1 audio interlude over 197 min - Ideal for travelers interested in Social Fabric & Everyday Life and Art, Design & Aesthetics - Immersively told in a podcast style by experts and locals - Matching audio content, AI guide and navigation through the app

Go bar hopping with a local resident with this casual, friendly walking tour of Portland's local bars. Your enthusiastic local guide will take you and your group to some of his favorite local haunts, with a heavy focus on interacting with locals and checking out the city's neighborhood vibes.

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.

Taste your way through Oregon’s renowned wine scene right in the heart of Portland! Try a variety of wine varietals and savor delicious bites, all while exploring the vibrant Pearl and Slabtown neighborhoods. What makes this wine tour special? We’ve met with the wine experts themselves and did all the research for you, so the tastings and snacks are curated and included. You’ll try 10+ wines at two winery tasting rooms plus one wine bar, including a variety of white, rosé, and red, and snack small bite pairings. Highlights: - Taste 4 Oregon wines paired with artisan popcorn at an approachable winery while learning why Oregon wine is special. - Explore 2 trendy Portland neighborhoods, blending old and modern architecture with rich history. - Dine on bruschetta paired with wine at a family-run winery. - End your evening sipping Bordeaux in a secret wine bar where you might just uncover a hidden surprise. - Learn from your tour guide and wine experts. *This tour is 21+ ONLY.

Escape the city for half a day—and explore the scenic highlights of the popular Columbia River Gorge—on this private tour. Pick between morning and afternoon start times, set off in a luxury Mercedes, and head into nature. You’ll discover stretches of the 74-mile (119-kilometer) highway, and immerse yourself in the Pacific Northwest scenery. Discover waterfalls like Latourell Falls and Multnomah Falls, admire Beacon Rock, stop at scenic viewpoints, and more.

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 3 participants to operate.

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.

There’s nothing better than exploring Astoria at your own pace, with a flexible itinerary tailored to your preferences. Step back in time and immerse yourself in the rich history of Astoria, Oregon's oldest American settlement. From its roots as a vital port city to its iconic landmarks, Astoria offers a perfect blend of history, natural beauty, and coastal charm. Discover its significant role in American exploration and maritime history, and enjoy breathtaking views of the Columbia River and the Pacific Ocean. This full-day tour takes you through the highlights of Astoria, offering a memorable journey through Oregon’s coastal heritage.

Immerse yourself in the beauty of Columbia River Gorge on this full-day trip from Portland to Mount Hood! With your small group, take a guided tour of such iconic Oregon destinations as Multnomah Falls and the famous Timberline Lodge, and enjoy lunch in the charming city of Hood River. Your tour also includes pickup from over 60 hotels in Portland and a private or small-group option.

Explore the stunning natural beauty of the Columbia Gorge with a unique blend of adventure and fine wine. This tour takes you to two breathtaking waterfalls in the morning, followed by wine tasting at two renowned wineries in the Hood River Wine Region and finishing with some free time to stroll through downtown Hood River. Gain insight into the region's geological history from your knowledgeable guide as you traverse scenic byways and enjoy views of majestic Mt. Hood and Mt. Jefferson. Whether you're a seasoned wine connoisseur or a casual enthusiast, this tour promises a day of exploration and discovery. - Visit beautiful waterfalls and two wineries in one day - Enjoy personalized attention on this semi-private tour - Pickup and drop-off service from the Portland Metro area - Tour duration typically runs from 9:00 AM to 5:30 PM

Explore the northern stretches of the Oregon Coast with a local guide on this private, customizable tour from Portland. You'll get to ride along the Pacific Coast Scenic Byway, take a hike through old-growth forest, and stop at one or two local towns or attractions of your choosing along the way.

Explore Portland with Operation City Quest! Our scavenger hunt takes you around the city to find items in any order you want and perform exciting tasks for points. The scavenger hunt is done using an app and you'll be able to check the rankings feature anytime to see how you rank. Our scavenger hunt has a remote guide that will help along the way via chat. Let's get exploring in Portland.

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.

Visit Mt. Hood and the Columbia Gorge, with a couple of stops for wine tasting along the way, with this full-day tour. You'll visit Multnomah Falls, the Columbia Gorge's most famous attraction, hang out at Mt. Hood's historic Timberline Lodge, and pay a visit to two different wineries to taste Gorge-produced wine. There will be a hosted lunch on tour and a glass of wine at one of the wineries included. You will also be able to purchase beverages at your leisure during winery visits.

Avoid falling victim to tourist traps and eat your way through the trendy Alberta Arts District with this walking food tour. Not only do you get to try treats from local eateries and food carts that line this hip neighborhood, but you also get to learn all about Oregon Pinot Noir from a local winemaker. A small group size keeps this guided tour feeling intimate.

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.

Learn about the haunted past of Portland, Oregon's Old Town with this guided ghost tour. Your guide will regale you with tales of the past as you walk to different allegedly haunted locations, wrapping up at Kells Irish Restaurant & Pub, believed to be haunted by a long-dead fire captain.