8-Day Oregon Winter Wonderloop

8-Day Oregon Winter Wonderloop

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All-Inclusive | Private Multi-Day Tour

9 Day/ 8 Night | Winter

This is the ultimate escape to experience Oregon’s most acclaimed destinations for skiing and snowboarding. Before and after hitting the slopes of Mt. Hood and Mt. Bachelor you’ll experience unique and exclusive activities, from snowshoeing at Crater Lake National Park to wine tasting in Willamette Valley, to chasing waterfalls in the Columbia River Gorge. Mix that with indulgent accommodations, exquisite dining and luxury transportation and you have all the ingredients for an ultimate Evergreen Escape!

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Day 1: Arrive in Portland

Arrive in Portland and meet your Evergreen Escapes guide at the airport as you are transferred to your luxurious hotel in downtown. This evening get to know the sights, sounds, and flavors of the Rose City. From its eclectic neighborhoods to its hip downtown and Pearl district, Portland features endless opportunities for foodies and urban explorers. Make sure to stop at a few of its iconic landmarks including the Pittock Mansion, Japanese Garden, and Powell’s Book Store. For dinner, enjoy a meal at one of Portland’s famous farm-to-fork restaurants.

Overnight: The Nines Hotel | Meals: D

Day 2: Columbia River Gorge | Wine & Waterfalls

Explore one of the greatest attractions of the Pacific Northwest – the Columbia River Gorge! Learn the ins and outs of the gorge while spotting for wildlife, before visiting, Multnomah Falls, the tallest waterfall in Oregon. Hike to two or three other secluded falls in this lush region with your naturalist guide and then savor a delicious seasonal meal in downtown Hood River. This afternoon, enjoy a flight of wine from two boutique wineries with views of Mt. Hood. Dinner is on your own this evening.

Overnight: Columbia Cliff Villas | Meals: B, L

Day 3: Mt. Hood | Ski Mt. Hood Meadows

Pull on the ski boots and mittens this morning as we make our way up to Mt. Hood for our first day of skiing. Join as hosted tour of the Mountain before striking out on your own to enjoy the mountains easy-going green runs, adventurous blue slopes, and challenging black diamond slopes. Tonight we’ll stop in Hood River for dinner together.

Overnight: Columbia Cliff Villas | Meals: B, D

Day 4: Mt. Hood | Snowshoe & Night Skiing

Enjoy a relaxing morning at your river-view room before we pack up and head back to the mountain. Mid-morning, we’ll go for a guided snowshoe hike at Cooper Spur and then lunch at the lodge. This afternoon, we will check into our overnight accommodations at 6,000 feet on Mt. Hood and grab an afternoon hot-toddy. Tonight, hit the slopes under the lights at the nation’s largest night skiing resort: Ski Bowl.

Overnight: Timberline Lodge | Meals: B, L

Day 5: Central Oregon | Smith Rock State Park & Bend

Say goodbye to Mt. Hood as we travel south and over the Cascades to central Oregon. Stretch your legs with a short nature hike at Smith Rock State Park and then enjoy an afternoon exploring downtown Bend with a brewery tour.

Overnight: Sunriver Resort | Meals: B, L, D

Day 6: Central Oregon | Mt. Bachelor

Grab those skis and boards again this morning for another fun-filled day of Skiing. Today we will head up to Mt. Bachelor. Ski through the glades on the lower runs all morning before heading to the mountain’s summit for big bowl slopes and amazing views of the central Cascade Mountains. Fill-up after a calorie-busting day with dinner at a local brewery or opt to try one of the resorts many on-site restaurants.

Overnight: Sunriver Resort | Meals: B, D

Day 7: Crater Lake National Park | Snowshoeing

As the sun rises over the rolling desert valley, we load up and make our way to the rim of Crater Lake, Oregon’s amazing National Park. Strapping on snowshoes, we will go for a wintry-walk, learn about this unique winter landscape and snap ample photos of the azure blue lake. Over hot-cocoa, learn about the unique geological history that formed this natural wonder.

Overnight: Sunriver Resort | Meals: B, L

Day 8: Return to Portland | Willamette Valley Wine Countywine-glass-barrell-room

Today, we will begin the journey back to Portland. Traveling back over the Cascade Mountains, we will drop down into the Willamette Valley and warm up with a little wine! Boasting more than 300 wineries and tasting rooms, the Willamette Valley wine country delivers on elegance but leaves pretense at the door. Tour the wineries and taste at two award-winning wineries today. Learn about the art of viticulture from your guide and sometimes the winemakers themselves.

Overnight: The Nines Hotel | Meals: B, L

Day 9: Departure

Say goodbye to Oregon and your guide on the way to the Portland International Airport for your return flight home.

Meals: B


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Day 1 Columbia Gorge

The Columbia Gorge is among the most rare and fascinating destinations on the planet.  On its way to the Pacific Ocean the mighty Columbia River has cut a deep canyon over 80 miles long through the heart of the Cascade Mountains, at points reaching depths of up to 4,000 feet (1,200 m) deep.  This magical place is home to majestic waterfalls, abundant wildlife, picturesque towns and breathtaking vistas. On the Historic Columbia River Hwy one leaves the present behind and travels back to a time when driving was about the journey, and not the destination.  See the landscape transform before your eyes as you travel from lush wet forests to high desert plains.

 Day 2 to 3 Mt Hood

is the highest point in Oregon, a dormant volcano, and the most climbed mountain in the US. The trip from Portland through the Columbia River Gorge and around Mt. Hood offers views of spectacular waterfalls, walks in pristine wine country, historic sites, and breathtaking mountain vistas.   No trip to the Mountain is complete without a visit to the historic Timberline Lodge, Oregon’s most treasured landmark.

Day 4 to 6 Bend

EverGreen Escapes van heading to Mt. Hood, OregonSituated on the scenic Deschutes River in the geographic center of the state, Bend is the most populated city in Central Oregon. To the east is high desert vegetation and to the west, Bend is surrounded by U.S. Forest Service land. The city is noted for its picturesque setting, mild climate, year-round recreation opportunities and growing economy. At an elevation of 3,625 feet, Bend enjoys the predominately dry climate of the Great Basin. Sunny days, cool nights and low humidity characterize the weather. Over the last century Bend has grown from a simple lumber settlement, to the thriving and vibrant urban center it is today with a rich cultural life.

Day 7 Willamette Valley LGBT group wine Sonoma County sml

The wondrous Willamette Valley was once known as the ‘promised land’ for the thousands of pioneers traveling west on the perilous Oregon Trail in the 1840s–1880s.  Today the Valley is a massively productive agricultural area that has become famous throughout the world for it’s pastoral farmland and delicious produce; most notably berries, hazelnuts and of course, world-class Pinot Noir!

Day 8 Portland

Also known as The City of Roses, Stumptown, Bridgetown, Beervana or Beertown, Portland is Oregon’s most populous city, and the third most populous city in the Pacific Northwest. Whether in the Cultural District downtown or a transfigured warehouse in the trendy Pearl District, it is easy to see why Money magazine has called Portland the “Best Big City” in North America. Portland is known for its large number of microbreweries and micro distilleries, as well as its coffee enthusiasm. Rich in Northwest arts and heritage, the city and region are also noted for strong land-use planning, excellent public transportation and a progressive regional-government.


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Please call or email for a tailor made version of this incredible adventure
Toll Free | 866-203-7603
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      • Hotel pick up & drop off each day
      • Highly qualified “Escape Artist” naturalist guide
      • Travel in adventure-outfitted Mercedes Vans and luxury SUVs
      • Scrumptious morning tea with pastries
      • Afternoon snacks, refreshments & fresh fruit
      • Locally &/or organic gourmet Cascadian Safari fare
      • On-board select Oregon wine
      • All overnight accommodations in select lodges & hotels
      • All tasting fees
      • All activities & equipment
      • All park entry fees
      • Comprehensive naturalist commentary throughout
Available as a private charter.  Please inquire for your personally crafted Escape Plan.



Starting from $6,525.00 per person based on double occupancy

Subject to change until confirmation.



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Please call or email for a tailor made version of this incredible adventure
Toll Free | 866-203-7603
Contact us

How to Pack and Prepare   |   FAQs   |   Terms & Conditions

[box] Please Note

  • It’s harvest season so exact farms, wineries and restaurants are subject to change based on accessibility
  • Subject to availability; single rates available upon request; price is subject to change until confirmed;


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EverGreen Escapes is Cascadia’s premier sustainable adventure travel company based in Seattle and Portland. Providing private and small group naturalist-led adventures in bio-fueled Mercedes vans. Specializing in crafting upscale and authentic nature, epicurean and education based experiences for the responsible, curious and discerning traveler.

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We know our destinations, but we don’t know you! Even if you’ve been inspired by one of our multi-day tours, we’ll need to know your hotel preferences, activity level, travel style, etc. to craft you the perfect Northwest travel experience and address logistical concerns such as the cost!

The more you share, the better we can source our knowledge, enthusiasm and personal connections to design an Escape Plan personalized to your interests and passions. An expert Escape Artist will contact you shortly to answer any questions you may have and start planning your trip!

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Thank you for Experiencing Cascadia with Evergreen Escapes!