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Portland, Oregon
Small group activities

Small group activities

Our most recommended Portland, Oregon Small group activities

Portland: Ghosts, Poltergeists, and Psychopaths Walking Tour

1. Portland: Ghosts, Poltergeists, and Psychopaths Walking Tour

Take a historic and memorable look at the haunted past of Portland, Oregon, with a 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 the Harlow Hotel 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 the 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 illegal trade that began to use these tunnels for gambling, opium dens, prostitution, and kidnapping. Follow your guide to some other haunted locations and hear, in gripping detail, the history of hauntings and paranormal activity.  Finally, make your way to the final stop at Kell's Irish Pub, where your guide can give you a 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: Willamette River 2.5-hour Dinner Cruise

2. Portland: Willamette River 2.5-hour Dinner Cruise

Whether you want to relax after a long day of sightseeing or need to unwind at the end of your workweek, a sunset dinner cruise along the Willamette River is sure to do the trick. The journey offers spectacular views of the Portland skyline and city’s main landmarks. Listen to live piano music while you enjoy a Pacific Northwest meal.

Portland: 2-hour Lunch Cruise on the Willamette River

3. Portland: 2-hour Lunch Cruise on the Willamette River

Enjoy lunch along the Willamette River on a 2-hour cruise in Portland. Great for newcomers and locals alike, the leisurely cruise presents an expansive vista of Portland from the water. In addition to exceptional views and food, the afternoon tour also includes commentary about the sights along the river and live piano music. Prepared with local ingredients, your meal comes with your choice of entrée from the menu and fresh baked bread. Side salad, appetizers and desserts are available for purchase on board.

Portland: Underground Shanghai Tunnel Tour with Beer Tasting

4. Portland: Underground Shanghai Tunnel Tour with Beer Tasting

Descend into an underworld beneath Portland on this guided walking tour of the city's Shanghai Tunnels. Learn all about the haunted history of the network of passages, then head upstairs for a well-earned craft beer tasting session. Meet your guide to hear stories of Portland's dark past, and hear all about the resident ghost, Nina. Explore these atmospheric tunnels as you uncover the stories of how they used to be used to transport unsuspecting sailors to ships docked on the river. Then, head back up to Old Town Pizza, located in the lobby of Portland's notorious former Merchant Hotel. A special beer tasting of award winning beer, before reflecting on your adventure while sipping on a delicious full pint.

From Portland: Columbia Gorge Waterfalls Tour

5. From Portland: Columbia Gorge Waterfalls Tour

Discover the scenic beauty of the Columbia River Gorge on a small group tour with an expert guide in a luxury passenger van. Explore Columbia River Gorge National Scenic Area, stopping at several picturesque waterfalls typical of the beauty of the Pacific Northwest. Depart from downtown Portland and drive towards Troutdale, known as the Gateway to the Gorge. Enjoy the journey along the Historic Columbia River Highway, the first planned scenic roadway in the United States. Arrive at Crown Point Vista House, an overlook that sits high above the Columbia River. From there, continue along the historic highway deep into the Columbia River National Scenic Area. Arrive at the first waterfall of the day, the dramatic Latourell Falls, which plunges 249 feet over a massive wall of columnar basalt.  You'll also have the chance to visit an often overlooked gem, Horsetail Falls, directly off of the historic highway. Once at the base of these falls, it won't be difficult to see how it received its name.  Proceed next to the grand Multnomah Falls, which plummets to the ground from 620 feet in two major steps. Explore the Multnomah Falls Historic Lodge and stand on the easily accessible viewing platform that offers a full view of the Benson Bridge and cascading falls beyond. Afterward, relax on the journey back to Portland via the Columbia River Gorge scenic route.

Portland: Mt. Hood Day Tour

6. Portland: Mt. Hood Day Tour

Your 8.5-hour trip begins early with a hotel pickup from downtown Portland. Embark on an exhilarating morning drive through the Columbia River Gorge. Catch spectacular views of the Cascade Mountains that flank the river and glimpse a waterfall or two. Along the forested highway, visit Oregon’s famous waterfall Multnomah Falls. Join your guide and fellow visitors on Benson Bridge and snap a picture of the 611-foot-tall cascade of water as it crashes below. Next, continue to Hood River, a picturesque valley town renowned as a prime destination for wind sports. Watch kiteboarders and windsurfers skate across the water as you learn about Hood River’s rich environmental and cultural history. Then take some free time for lunch, shopping or wine-tasting (if whimsy strikes you!). Then visit Rowena Crest which has spectacular views of the Columbia River Gorge. The final stop on your guided tour is the glorious Mount Hood, Oregon’s tallest peak at 11,249 feet (3,429 meters) and Timberline Lodge. Take a mountain walk or a self-guided visit through the renovated lodge that was once the setting for the classic film The Shining. Your day concludes back in Portland by early evening.

Portland: Champagne Brunch Cruise on Willamette River

7. Portland: Champagne Brunch Cruise on Willamette River

Portland is known for its love of brunch — elevate your Portland brunch experience with a cruise on the Willamette River! Enjoy a 2-hour cruise through Portland and Milwaukie, Oregon, and all-you-can-eat buffet prepared fresh on board, hosted champagne/mimosas, live piano entertainment and a narration of the sights on the outer decks. We will make sure to keep the coffee and the champagne flowing, all you need to do is relax and take in the views. You will have a dedicated server at any point during the cruise they will be able to help you make sure it is an amazing experience.

Multnomah Falls: Waterfall Corridor Hop-On Hop-Off Trolley

8. Multnomah Falls: Waterfall Corridor Hop-On Hop-Off Trolley

Create your own adventure along the historic Colombia River Highway, including iconic Multnomah Falls. Hop off at any of the stops to explore trails and waterfalls. Trolleys arrive at each stop every hour, so you have plenty of time for a short stop with pictures or a longer hiking excursion. Entry tickets now required by the National Forest Service are included in your reservation. Parking is free at our nearby Corbett parking lot so that you can avoid all the parking waiting and traffic. If you just want to ride the Trolley and listen to the guided narration, a round trip lasts about an hour and forty-five minutes. As you journey between the locations, enjoy the fantastic views from the open-air trolley that features unobstructed perspectives, perfect for snapping photos and taking in panoramic landscape views. A detailed hiking/stop guide is available when you board the Trolley, and suggested itineraries are available on our website. Stops are made at the following locations: Corbett • Crown Point • Latourell Falls • Bridal Veil Falls • Angels Rest • Wahkeena Falls • Multnomah Falls • Triple Falls • Horsetail Falls • Ainsworth

Portland: Happy Hour Sightseeing Cruise

9. Portland: Happy Hour Sightseeing Cruise

Board the Portland Spirit and embark on a tour of Portland and the Willamette River from an entirely new perspective. Learn about the area, people and bridges from the historical narration, played on all three levels. You may sit indoors in the climate-controlled areas or outside in the open air. Take in the views of the Portland and Milwaukie waterfronts with a full-service bar and bistro menu available for purchase. The cruise will head south on the Willamette River to Milwaukie and then back to the dock.

Portland: Guided Delicious Donut Tour with Tastings

10. Portland: Guided Delicious Donut Tour with Tastings

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, Voodoo Doughnuts and more. 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, Oregon

Portland, Oregon

Frequently asked questions about Portland, Oregon Small group activities

What are other things to do than Small group activities that are worth visiting in Portland, Oregon?

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Other Sightseeing Options in Portland, Oregon

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What people are saying about Portland, Oregon

This was a fantastic tour run by a funny, engaging plucky local. His passion for food and the food scene in Portland radiates throughout the tour. He takes you to the best food trucks and shows you what is special about them. He partners with one of the best chocolate shops I have visited in the world (and I travel a lot). This is the first place I've eaten dark chocolate and liked it. He knows the history of the city and shares it with you. And at the end he askes you to pick your favorite item and it's impossible to choose because everything on the tour was truly that good. You not only get good food, and a great history lesson on the city, but you also get to truly see the character of the city and it's people. He partners with small, local shops, and you see how friendly everyone is, and they want to share their city with you. 10/10. Must do.

We were in Portland for 3 nights and this was BY FAR the highlight. We can't stop talking about it at home. David clearly loves Portland and that made us love it, too. His choice of food carts and other treats was so wonderful. Personal history with the places and food relationships with the vendors was impressive. Everything was so fun and week worth whatever the cost. Do yourselves a favor and book this!

Very enjoyable day with Wayne, our guide. He really understood our wine tasting objectives and focused on making sure we met the most interesting growers and wine makers. Thanks Wayne; you’re a star!!

Marcus is an excellent guide! I can tell you for sure You won’t have any guide like him. He is a cult, competent guy… if you really want To get a real Experience of Portland… Book this tour!

Loved the variety of the activities and the tour was the perfect amount of time. Marcus was great!