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Top Day Trips from Oregon (Updated November 2026)

Oregon, USA
The Hood-Columbia Loop: Timberline, Orchards, and Waterfalls

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by …More

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by...

8 hours Hotel pickup offered Free Cancellation
4.9 (14)
from
$139
Bed and Breakfast Wine Tour - Small Group, Joinable/Sharable

Home to some incredible bed and breakfasts, Newberg Oregon is centered in the heart of Oregon Wine Country. While you don't have to stay with …More

Home to some incredible bed and breakfasts, Newberg Oregon is centered in the heart of Oregon Wine Country. While you don't have to stay with...

6 hours 30 minutes Hotel pickup offered Free Cancellation
5.0 (6)
from
$230
Private Tour of Multnomah Falls and Columbia Gorge

There is no better way to discover the Columbia River Gorge, a must-visit destination when you're in Portland, than on a private tour just for …More

There is no better way to discover the Columbia River Gorge, a must-visit destination when you're in Portland, than on a private tour just for...

4 to 5 hours Hotel pickup offered Free Cancellation
5.0 (39)
from
$129
Full-day Columbia Gorge Hiking

The 85-mile (137-km) long Columbia Gorge NSA would be a national park if it weren't a critical transportation corridor. It features waterfalls, mountains, monoliths, terraces, …More

The 85-mile (137-km) long Columbia Gorge NSA would be a national park if it weren't a critical transportation corridor. It features waterfalls, mountains, monoliths, terraces,...

8 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$149
Private Mt Hood Waterfall Tour with Lunch and Wine included

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by …More

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by...

8 to 9 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$175
Full Day Jet Boat Tour in Hells Canyon

Spend an entire day traveling through Hells Canyon and experience wildlife, swim in the fresh water, visit our historical sites and museums and more! This …More

Spend an entire day traveling through Hells Canyon and experience wildlife, swim in the fresh water, visit our historical sites and museums and more! This...

5 to 6 hours
4.9 (14)
from
$219
Private - Mt Hood & Columbia River Gorge Waterfalls Tour From Portland

Join an intimate, Oregonian-led Private tour of the Columbia River Gorge and Mt Hood with Portland, Oregon's original tour and adventure company. Your seasoned, local …More

Join an intimate, Oregonian-led Private tour of the Columbia River Gorge and Mt Hood with Portland, Oregon's original tour and adventure company. Your seasoned, local...

9 hours
5.0 (2)
from
$200
Private Northern Oregon Coast Day Trip

This day trip is a customized tour along a section of rugged coastline along Oregon's northern coast. There will be one or two town stops, …More

This day trip is a customized tour along a section of rugged coastline along Oregon's northern coast. There will be one or two town stops,...

8 to 9 hours Hotel pickup offered Free Cancellation
5.0 (4)
from
$1,526
Private Tour at The Hood-Columbia Loop: Timberline, Orchards, and Waterfalls

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by …More

Mt. Hood is the highest summit in Oregon, and the fourth highest in the Cascades. It features waterfalls, glaciers, and historic Timberline Lodge, built by...

8 to 10 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$1,652
Private Back-Country Distillery, Brewery, or Pub Tour

The perfect sanctuary for men to escape the toils of daily life, fill their gullets with fine crafted spirits and brews, and beat their chests …More

The perfect sanctuary for men to escape the toils of daily life, fill their gullets with fine crafted spirits and brews, and beat their chests...

8 hours Free Cancellation
5.0 (4)
from
$230
Silver Falls Private Hike Tour

There’s no better way to experience the magic of Silver Falls State Park, a true gem of Oregon, than on a private tour. From its …More

There’s no better way to experience the magic of Silver Falls State Park, a true gem of Oregon, than on a private tour. From its...

4 to 5 hours Hotel pickup offered Free Cancellation
5.0 (5)
from
$109
Portland Private Tour Adventure for Small Groups (Customizable)

Create Your Perfect Oregon Adventure! Your tour, your way! Choose from the destinations and experiences listed in the itinerary, or let us create something entirely …More

Create Your Perfect Oregon Adventure! Your tour, your way! Choose from the destinations and experiences listed in the itinerary, or let us create something entirely...

2 to 9 hours Hotel pickup offered
4.9 (9)
from
$699
Oregon Coast Tour and Wine Tasting From Portland- Full Day Tour

The Oregon coast is one of the most majestic geologic formations that was formed by lava flows millions of years ago. We depart to the …More

The Oregon coast is one of the most majestic geologic formations that was formed by lava flows millions of years ago. We depart to the...

8 to 9 hours Hotel pickup offered
5.0 (8)
from
$150
Private wine tour with local Sommelier.

Unlike a typical wine tour, we will stroll through gorgeous vineyards with the winemakers themselves, explore barrel rooms (possibly taste from the barrel!) and experience …More

Unlike a typical wine tour, we will stroll through gorgeous vineyards with the winemakers themselves, explore barrel rooms (possibly taste from the barrel!) and experience...

6 to 9 hours Hotel pickup offered Free Cancellation
5.0 (3)
from
$2,250
Willamette Valley Wine Tasting Tour

The best wineries in Oregon lie just under an hour’s drive from Portland in the Willamette Valley, a thriving wine region known for its outstanding …More

The best wineries in Oregon lie just under an hour’s drive from Portland in the Willamette Valley, a thriving wine region known for its outstanding...

5 hours 30 minutes Hotel pickup offered Free Cancellation
5.0 (2)
from
$138
Mt Hood Loop Tour including Multnomah Falls

Join us on our full day guided tour from Portland to Mt. Hood. By visiting Mount Hood with our enthusiastic and knowledgeable guides, you will …More

Join us on our full day guided tour from Portland to Mt. Hood. By visiting Mount Hood with our enthusiastic and knowledgeable guides, you will...

8 hours 30 minutes Hotel pickup offered Free Cancellation
5.0 (4)
from
$133
Winter Focused Willamette Valley Wine Tour (Tastings Included)

Are you looking for the romantic, quaint or cozy tastings rooms in Willamette Valley, but also want to experience some of the best boutique wineries …More

Are you looking for the romantic, quaint or cozy tastings rooms in Willamette Valley, but also want to experience some of the best boutique wineries...

6 to 9 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$239
From Portland to Mt. Rainier Tour in a Small Group

Discover the rugged beauty of the Mt Rainier National Park on this full-day trip. Travel aboard a comfortable van through historic Gold Rush towns to …More

Discover the rugged beauty of the Mt Rainier National Park on this full-day trip. Travel aboard a comfortable van through historic Gold Rush towns to...

8 to 10 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$350
Private Willamette Valley Wine Tour

Jeff Davies has 30+ years of guiding Willamette Valley Wine Tours. I have top reviews on Cool Shore Excursions, Google and Yelp for Private Tours …More

Jeff Davies has 30+ years of guiding Willamette Valley Wine Tours. I have top reviews on Cool Shore Excursions, Google and Yelp for Private Tours...

6 to 9 hours Hotel pickup offered Free Cancellation
5.0 (2)
from
$1,292
Private Multnomah Falls and Mt. Hood Tour with Gorge Waterfalls

Jeff Davies has 30+ years of guiding the Multnomah Falls / Mt. Hood "Loop" Tour with Columbia River Gorge Waterfalls. I have top reviews on …More

Jeff Davies has 30+ years of guiding the Multnomah Falls / Mt. Hood "Loop" Tour with Columbia River Gorge Waterfalls. I have top reviews on...

8 to 9 hours Free Cancellation
5.0 (3)
from
$1,334
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