Oregon
Seasonal & Holiday Activities

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Our most recommended Oregon Seasonal & Holiday Activities

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: 2 Hour Lunch Cruise Through Downtown

3. Portland: 2 Hour Lunch Cruise Through Downtown

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

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Portland: Columbia Gorge Waterfalls 40-Minute Scenic Flight

4. 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.

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Cascade Locks: 2-Hour Columbia River Gorge Dinner Cruise

5. Cascade Locks: 2-Hour Columbia River Gorge Dinner Cruise

Take your favorite person to a romantic dinner on the beautiful Columbia Gorge as you learn about the area in the historical Columbia Gorge Sternwheeler boat in Cascade Locks, Oregon. Start your experience with the meal service which includes freshly-baked bread, a house salad, your choice of a plated entrée, and a house dessert. For the plated entrée, you will have a choice onboard between poultry, beef, vegetarian, or seafood. During the meal, take in the sights on the Columbia River while the captain narrates the history and folklore that makes the gorge so unique.

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Portland: Private Columbia Gorge Air Tour

6. Portland: Private Columbia Gorge Air Tour

As one of the most popular flights offered, this incredible air tour is a great way to experience the grandeur and beautify of the Columbia River Gorge at a very incredibly low price. Enjoy this experience privately for up to 3 people and prepare yourself for a beautiful aerial tour of one of Portland's most famous tourist areas. On this tour, you will be afforded beautiful views of the Columbia River, Mt. Hood, the popular viewing area called Crown Point, Latourell Falls, and so much more. This tour is a wonderful experience at sunset, and will be sure to create long lasting memories.

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Bend: Half-Day Snowshoe Tour in the Cascade Mountain Range

7. Bend: Half-Day Snowshoe Tour in the Cascade Mountain Range

Venture into the wilderness areas around Mt. Bachelor and the surrounding Deschutes National Forest of the Cascade Mountain Range of Oregon. Experience the magic of the snow-laden trees, inspect animal tracks, and bask in the quiet of the winter forest. Enjoy a great opportunity for snow play suitable for a wide range of ages and ability levels. Snowshoe tours are customized for all adventure desires— stroll easily on flatter areas, or leap off powder-covered lava flows and get “air” like you never imagined. Let your guide do the driving and teach you fun snowshoeing techniques and tricks as all tours include instruction. Remember to wear winter boots and powder/ski pants to keep your feet and legs dry while snowshoeing.

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Cascade Locks: Columbia Gorge Sunday Brunch Cruise

8. Cascade Locks: Columbia Gorge Sunday Brunch Cruise

After boarding in Cascade Locks, you will be taken to your private table. The first half of the experience is the meal service where you will enjoy a plated brunch where we keep the coffee and the champagne flowing. The brunch will consist of breakfast, lunch, and dessert items. During the last half of the cruise, there will be narration provided of the sites being passed. 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.

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From Portland: Willamette Valley Character Wineries

9. 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.

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From Portland: Columbia Gorge Hike and Winery Lunch

10. From Portland: Columbia Gorge Hike and Winery Lunch

Hike the forests and steppes of the Columbia Gorge, discover the natural and cultural history of the area, and get intimate with the most climatically diverse wine region in the USA on this small-group tour. Together with the other members of your group, learn about the history, terroir, and character of Columbia Gorge wine from your wine industry-honed interpretive guide. This day trip is a customized tour of up to 15 km of hiking, depending on the physicality of the group, 2 tasting room visits, and a visit to the Columbia Gorge Discovery Center and Museum. In the morning, travel east of Portland as your guide takes you through the dramatic cliffs, terraces, and monoliths of the Columbia Gorge, a sea-level passage through the Cascades, containing the highest density of hanging waterfalls in the world. Stop at a fruit stand or fish stand for a bite to eat if you wish. After spending the morning hiking this sublime landscape, stop for lunch at a boutique winery, where you can taste wine in a historic building with a fascinating story. After lunch, visit the Columbia Gorge Discovery Center and Museum, where you can peruse the interpretive displays for more in-depth information on the natural and cultural history of the Columbia Gorge. Afterward, wander through the valleys, terraces, and synclines of the Columbia Gorge wine region, passing through charming little villages, while making another stop at a unique winery. Finally, head back to Portland and get dropped off at your hotel.

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Other Sightseeing Options in Oregon

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What people are saying about Oregon

In spite of the rain, we enjoyed a delightful cruise and the dinner was delicious and it was plentiful! The info the Captain was giving was hard to hear but when I did catch a little it was very interesting. I would recommend this cruise to anyone! Katie was our server and she was the best!

Our guide was very well connected to the tales of the underworld and historic spooky facts of old Portland.

It was our first time. Very nice and relaxing. The food was great too. We will be doing it again soon

Food was good. Service good. Piano music during dinner was a nice treat. View was beautiful.

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