Portland Overnight & Multi-Day Tours

Small-Group Multi-Day Tours from Portland:

Our guided multi-day trips are an excellent way to get more from your time exploring the Northwest. On our small-group trips, you’ll join a few other world travelers, play outside plenty, immerse yourself in world-class landscapes, eat & sleep well, and experience more!

How to join a small group of travelers in the Pacific Northwest on a multi-day tour from Portland:


Choose Your Tour & Date

The multi-day tours below explore ‘can’t miss’ destinations in the Pacific Northwest from Portland, Oregon. Small groups, a great tour guide, and all-inclusive tours. This isn’t a big bus tour – let’s explore!


Traveler Info & Deposit

Click on any of the blue buttons below to see trip specifics and Portland tour booking details. After you’ve decided on your trip – we’ll ask for limited personal info and a deposit to hold your place.


We’ll Take it From There!

You bring appropriate layers and sturdy shoes. We’ll bring everything else: a comfy touring van, an easy-to-love guide, food, plenty of snacks and refreshments, and any gear needed.

3-Day Hiking Tour

Columbia Gorge and Mt Hood Hiking

Wind your way down Waterfall Alley, tackling rushing rapids on a whitewater rafting trip, learning about the natural history of the region, and topping it all off with a fine dining experience at Mt. Hood’s historic Timberline Lodge. There is no better way to see Columbia River Gorge and Mount Hood than with an expert guide and a small group.

Tour Dates 2021

Jul 7-9
Jul 21-23

5-Day Hiking Tour

Columbia Gorge and Mt Hood Hiking

Hailed as one of Oregon’s Seven Wonders, the region’s fleece-capped mountain peaks, primeval forests, abundant wildflowers and waterfall-streaked highlands whisper of the Swiss Alps. Learn about the rich natural history of the region as we visit each of these diverse environments up close, including a whitewater rafting trip down a spectacular gorge. From Multnomah Falls to Hood River to Mount Hood, easy to reach trails abound, making this the ideal location for a hiking tour. 

Tour Dates 2021

Jun 28-Jul 2

2-Day (Overnight) Tour

Mt. St. Helens Hiking Tour

If you are looking the best way to spend 3 days in inspiring wilderness getting to know Washington’s most-storied mountain, this tour is for you. We take in incredible vistas and keep our feet moving, exploring the various Simply put, Mount Saint Helens is unlike any landscape you have witnessed before… If you want to really explore this once-devastated landscape on foot and learn the story behind the most famous event in Washington State’s geologic history, this is the tour for you! of this geographic landmark and the remarkable terrain which surrounds it. Wildlife abounds. There is no better place for viewing than in the Park!

Tour Dates 2020

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3-Day Hiking  Tour

Crater Lake & Mt. Hood

Enjoy three days of non-stop scenery on this tour of the Oregon Cascades region. Hike to a tranquil mountain lake with views of Mt. Hood on your way to the stunning rock formations along the Crooked River near the outdoor mecca of Bend, Oregon. Spend a day hiking at Crater Lake National Park. Hike through a wildflower “forest,” and a rainforest – both on the same day! Relax for two nights at the historic McMenamins Old St. Francis School in Bend, Oregon. There is no better way to see Crater Lake, Mount Hood, and the Oregon Cascades than with an expert guide and a small group!

Tour Dates 2020

Call to Book

5-Day Hiking

Oregon Crater Lake Hiking

A surprise awaits you around nearly every corner of this 5-day tour! Beginning and ending in Portland, Oregon, take an amazing trip through the ecological and geological diversity of central Oregon. Truly a nature lovers’ playground, the Oregon Cascades are a showcase for snow-capped volcanoes, lava fields, lava cones, high deserts, rainforests, pine forests, waterfalls, hoodoos, mountain lakes, wildflower meadows, and more. Come see for yourself why the outdoor mecca of Bend, Oregon is ranked as one of the most enviable cities to live – in the world! Culminating on the shores of the deepest lake in the United States, Crater Lake, words and photos inevitably fail to convey the depth of either the water or the emotions of the observer who first looks into the “crystal ball” of this collapsed volcano. It simply must be experienced. Our naturalist guides will connect you to the area. There is no better way to see Crater Lake, Mount Hood and the Oregon Cascades than with an expert guide and a small group!

Tour Dates 2020

Call to Book

3-Day Hiking

Oregon Coast Hiking

Check one of the “Seven Wonders of Oregon” off your bucket-list and enjoy three days of non-stop ocean views, emerald forests, crashing waves, beaches, and sea stacks on this tour of the northern Oregon Coast. Relax for two nights in the charming seaside town of Cannon Beach in view of Haystack Rock – one of the area’s most iconic images. Hike in three of Oregon’s widely acclaimed State Parks. Timing your visit for good low-tides reveals another world beneath the sea. There is no better way to see and experience the Oregon Coast than with an expert guide and a small group!

Tour Dates 2020

Call to Book

Contact our team to learn more about Portland tours.

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Private Multi-Day Tours from Portland
New Webpages Coming this Summer!

While the scheduled small-group multi-day tours found above are also available as private escapes – the tours below are only available as private explorations. Contact our team to learn more or to schedule your private multi-day adventure today!

2-Day Oregon Coast Private Tour

2-Day Columbia River Private Gorge Tour

2-Day Willamette Valley Wine & Waterfalls Private Tour

3-Day Bend, Oregon PrivateTour

Prefer to browse single-day tours instead?

1-Day Tours from Portland1-Day Tours from Seattle

Multi-Day Tours from our Sister Company, Bicycle Adventures.

Evergreen Escapes shares the Pacific Northwest with our lovely sister company – Bicycle Adventures! Looking for an escape on a date we don’t offer a trip or want a long cycle ride in a beautiful place? Look no further – Bicycle Adventures! The links below will take you to their website.

Custom dates available – call to book!

4-Day Tour: Bend Breakaway

The ultimate cosmopolitan mountain town…snowcapped peaks punctuate the high-desert skyline. Roads are dreamy-smooth. And the weather? Some of the best in Oregon!

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6-Day Tour: Hells Canyon Bike

Open prairie vistas and serene farmland into the breathtaking Eagle Cap Wilderness. Alpine lakes surrounded by the Wallowa Range. Take a tramway to the top of Mount Howard & ride deep into Oregon’s Hells Canyon.

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4-Day Tour: Oregon Wine Country

On this most romantic tour, explore the tranquil back roads, covered bridges, and vineyards of this enchanting area. It’s also ideal for those with differing ability levels or who have limited vacation time. Mouthwatering dining and impeccable lodging, plus a few delightful surprises, make this tour truly special.

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