4-Day Tour: Crater Lake National Park, Willamette Valley Wine, & Mt. Hood

4-Day Tour: Crater Lake, Mt. Hood, & Willamette Valley
‘Beyond Crater Lake’ Tour

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This adventure, exploring both sides of the Cascade Mountain Range, offers up a beautiful diversity of landscapes. Experience Pacific Northwest rainforest, rocky sub-alpine terrain, and expansive views from a high point of nearly 8,000’ in Crater Lake National Park. Though Crater Lake is the primary destination of your tour, two of Oregon’s state parks – the towering cliffs of Smith Rock and the tumbling waterfalls of Silver Falls – are bound to leave a lasting impression. Experience local cuisine along the way – not to mention Oregon’s abundant fine wines and famed craft brews.

Tour Overview



Tour Dates 2020


Tour Price

$3000 per person.
Additional $300 single-occupancy rate required for solo travelers.

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Tour Details


Day 1: Mt. Hood to Bend, Oregon

Timberline Lodge, Deschutes River, Warm Springs Canyon, & Bend, OR

Our first day on the road takes us into the Cascade Mountain Range, as we travel to Timberline Lodge at 6,000’ above sea level. Crisp, cold snow-melt tumbles over Umbrella Falls, and when the wind is flat beneath clear skies, the view from Trillium Lake is iconic.

Descending from the mountain, we follow the Deschutes River through Warm Springs Canyon, to the dizzying Crooked River Canyon Overlook, and discover an entirely new eco-region: Oregon’s High Desert. The air is hot and dry, and we adjust to the elevation at Smith Rock State Park along the blue and green ribbon that is the Crooked River, where millennia of volcanic ash compacted into the unique rock formations. The vertical faces inspired the founders of sport-climbing, the dominant form or rock-climbing today, and with any luck, we’ll see climbers scrambling up the rock this afternoon. Finally, we arrive in the oasis of Bend, OR possessing a population near 100,000 and among the most breweries per capita of any city in the United States. It’s a city for the young and the young-at-heart, expressed in the near-universal participation in outdoor pursuits from mountain biking to paragliding and everything in between. Dine tonight with your fellow travelers as they do in Bend – casual fare at one of the city’s many microbreweries.

Logistics: From Portland, we travel east to Mount Hood and into the High Desert. From our comfortable, big-windowed, high-roof van we’ll watch this new landscape spread out in front of us with its big skies and long vistas. Today, we’ll make stops at Timberline Lodge, the Museum at Warm Springs, Crooked River Canyon, and Smith Rock State Park before arriving in Bend, OR. We’ll call the McMenamin’s St. Francis School home for three nights; once a Catholic schoolhouse – it’s been converted into a gorgeous hotel complete with theater, restaurant, well-stocked pub, and soaking pool.

Walking Distances:

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Day 2: Crater Lake National Park

Rim Drive, Cleetwood Cove, Picnicking, & Sunriver Resort

Today, the highest point in the National Park is the summit of Mt. Scott, at 8,929 feet above sea level, but the peak of Mt. Mazama was the highest in Oregon before its phenomenal eruption and implosion 7,700 years ago. It’s a singular destination, which is often summed up by your first words on reaching the crater rim: Wow.

Your guide will bring the National Park alive today, as you circumnavigate the Rim Drive, stopping at as many viewpoints as your camera lens can accommodate, and selecting appropriate walks and hikes. This could be the well-worn trail to Cleetwood Cove, the only place you can dip a hand in the water, to Mt. Scott, the Watchman Overlook, or the easy walks at Sun Notch and the Castle Creek Wildflower Trail. We’ll bring a picnic lunch with us today, and hope to enjoy it overlooking the pristine waters of the Lake. Travel time to the Park is significant, so we embrace it on this long day, using all the sunlight available, and allowing for some independent time at Crater Lake Lodge or the visitors center. On the return drive to Bend, we stop in to dine together at Sunriver Resort.

Logistics: Crater Lake is south of Bend approximately 1 hr and 45 minutes, so once in the Park, we get out of the van as frequently as possible! Park entrance is included, and Park Collectors will absolutely have the chance to stamp their National Park Passport book. There are very few amenities along the way, so we bring along our picnic lunch and stop in at Sunriver Resort for dinner in the evening.

Walking Distances:

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Day 3: Choose Your Adventure in Bend, Oregon

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An independent day with plenty of options facilitated by your guide.
Bend has become a widely-known adventure sports mecca in recent years, and is a veritable outdoor & cultural playground. Your guide will help you plan the perfect day, including offering a number of optional local tour opportunities and activities.
Set your own pace today….. (brewery tour, Paulina Plunge, whitewater rafting, High Desert Museum, half-day hiking with your guide… TBD)

Walking Distances:

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Day Four: Willamette Valley

Silver Falls hiking & wine tasting!

This morning we’ll have breakfast in Sisters, Oregon as we approach Santiam Pass, a more southerly route across the Cascade Mountains. The subalpine is behind us, and the High Desert fades away as we enter the Willamette Valley, stopping in the rain forest of its eastern edge in Silver Falls State Park. Nature walks bring us to two stunning waterfalls where short walks lead us behind the curtain of falling water.

Our journey ends this afternoon with a relaxing treat. Revel in the rolling hills and scenery of Willamette wine country, and experience pinot noir, the wine varietal that made the region famous. Enjoy a winery lunch.

Logistics: Leaving Central Oregon over Santiam Pass carries us through Sisters, OR and threads the needle between volcanic Black Butte and the peaks of Mt. Washington and Three-Fingered Jack. Pass dramatic evidence of forest fires and the lakes of the popular summer destination of Detroit Lake before descending into Oregon’s agricultural heartland, the Willamette Valley. Spend time on the trails of Silver Lake State Park before enjoying the region’s fine wines. Finally, continue north to Portland, arriving in time for evening flights, or dinner in the city before enjoying other local adventures.

Walking Distances:

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The Pacific Northwest is waiting for you!

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Additional Tour Information

4-Day Tour from Portland: Crater Lake, Mt. Hood, & Willamette Valley Tour

Traverse the Mt. Hood National Forest, including a visit to historic Timberline Lodge.

Experience the extreme dichotomy of landscapes in Oregon: the verdant forests of Western Oregon, and the high desert of Central Oregon.

Relax near the jewel blue waters of Crater Lake and learn the volcanic history of Mount Mazama.

Feel the mist of waterfalls at Silver Falls State Park in the Cascade foothills.

Savor pinot noir in the world-renown Willamette Valley wine country.

You'll sleep soundly in the heart of Olympic National Park in private, comfortable mobile mini-cabins outfitted by our friends at ROAM Trailers! All lodging costs are included in our pricing.

You'll be guests of ROAM Beyond, staying in Homegrown Trailers featuring a queen bed (plus bunks), robust solar power systems, advanced battery storage, hot water and shower, induction cooktop with pots & dishes, cold refrigerator and freezer, plenty of power for lighting and charging devices, plus a self-contained toilet. Linens with a warm comforter and duvet cover will be included along with pillows, towels, and biodegradable soaps.

Join a small group (a maximum of 10 travelers total). This adventure is $1500 per person after all taxes.

This trip does require, at minimum, that three travelers book any given date. If our trip doesn't reach it's three guest floor - all booked travelers will be notified in advance and refunded fully.

To book a public trip, we ask for $250 to reserve your spot on the trip. 60 days out we'll ask for a 50% deposit as we prepare for your trip. 30 days out we'll request the final balance.

Want to make your adventure private? Prices below are before WA Sales Tax (10.1%). To inquire about private trip dates, give us a call!

1 person: $4100/person

2 people: $2400/person

3 people: $1900/person

4 people: $1600/person

5 people: $1400/person

6 people: $1250/person

7 people: $1150/person

8 people: $1000/person

9 people: $975/person

10 people: $950/person