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

4-Day Tour from Portland, Oregon:

‘Beyond Crater Lake’ Tour

tours seattle portland mountain icon

This tension-erasing escape visits Oregon’s only National Park – epic Crater Lake, mixes in divine wine from America’s largest grape growing & winemaking region – the Willamette Valley, explores Bend, and winds up Mt. Hood! 

This tour, 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-ft 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.

Book A TourAsk A QuestionEvergreen Escapes TripAdvisor Hall of Fame Certified Excellent

Tour Dates 2020

July 1-4
July 13-16
August 31 – September 3
September 14-17

Tour Price

$1800 per person.
Additional $300 single-occupancy rate required for solo travelers.

Tour Overview

Crater Lake National Park is a spectacle to behold – it may be our favorite spot to catch a sunrise or sunset in the Western USA. This tour offers experiences in some of Oregon’s finest landscapes on a thorough exploration of both flanks of the impressive Cascades Mountains and the historic regional volcanism that created Crater Lake. Western waterfalls, wine, and wandering…what could be more perfect?

Top it all off with Willamette Valley wine country and you have a recipe for a relaxing 5 days in the wilds of Oregon.

Crater Lake is waiting for you! Find your tour.

Book A TourAsk A Question

Day 1: Mt. Hood to Bend, Oregon

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

Our first day on the road takes us into the Cascade Mountain Range as we travel up to Timberline Lodge, 6,000-ft above sea level. We’ll explore several spots around Mt. Hood this morning, including the meditative Umbrella Falls and magnificent Trillium Lake for an unbeatable view of Mt. Hood.

Descending from the mountain in the afternoon, we’ll follow the Deschutes River through Warm Springs Canyon to the dizzying Crooked River Canyon Overlook. It’s here where we’ll discover an entirely new eco-region: Oregon’s High Desert, where the air is hot and dry. We’ll adjust to the change in elevation at Smith Rock State Park, along the blue and green ribbon that is the Crooked River, where millennia have transformed volcanic ash into these unique rock formations. The vertical faces here inspired the founders of sport-climbing, the dominant form of rock-climbing today, and with any luck, we’ll see climbers scrambling up the rock this afternoon.

We’ll complete our first day in the oasis of Bend, OR, our home base for the next three nights. Bend is 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. It also ranks among the highest for U.S. cities for number of breweries per capita. Dine like a local tonight in the company of your fellow travelers with casual fare at one of the city’s many fantastic microbreweries.

Walking Distances: 2 miles
Accommodations: McMenamin’s St. Francis School

– 1 –

Day 2: Crater Lake National Park

Rim Drive, Cleetwood Cove, Watchman Overlook, & Sunriver Resort

Today is all about Crater Lake – Oregon’s only National Park! It’s a singular destination, which is often summed up by the first word uttered upon reaching the crater rim: Wow. The highest point in Crater Lake National Park is the summit of Mt. Scott, 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.

We’ll bring the National Park alive today, circumnavigating Crater Lake on the historic Rim Drive, a 33-mile loop boasting epic views of the lake and surrounding forests and meadows. We’ll have a variety of options to explore all that this destination to offer, whether walking the well-worn trail down to Cleetwood Cove, the only place you can dip a hand in the water, strolling on some relaxing trails through wildflowers, or heading up to Mt. Scott and the famous Watchman Overlook.

One of our stops along Rim Drive will second as a perfect spot for our picnic lunch, and everyone will enjoy some free time at Crater Lake Lodge or the Park Visitor’s Center (an opportunity to get your National Park Passport stamped)! On our return to Bend, we’ll stretch our legs and enjoy dinner together at Sunriver Resort, a destination of its very own.

Walking Distances: Flexible options
Accommodations: McMenamin’s St. Francis School

– 2 –

Day 3: Bend, Oregon

Choose Your Own Adventure!

Set your own pace today with a day all your own. There are plenty of options to choose from (remember that Bend is THE destination for outdoor adventure) – and your guide will be there to help you plan the perfect day.

A veritable outdoor and cultural playground, these are some of the activities on offer in and around Bend today:
 A half-day of hiking
 Whitewater rafting
 Brewery tour
 Downtown Bend and the High Desert Museum
 Mountain biking and swimming the Paulina Plunge

Walking Distances: Depends on your choices!
Accommodations: McMenamin’s St. Francis School

– 3 –

Day 4: The Willamette Valley

Silver Falls hiking & wine tasting!

This morning we’ll have breakfast in Sisters, OR as we approach Santiam Pass, a more southerly route across the Cascade Mountains. This pass will carry us between volcanic Blake Butte and the peaks of Mt. Washington and Three-Fingered Jack. 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 at Silver Falls State Park. We’ll sojourn here for a refreshing nature walk, leading us out to two stunning waterfalls and behind a curtain of falling water.

As we journey on, revel in the rolling hills and scenery of Willamette wine country, and experience pinot noir, the wine varietal that made the region famous! We’ll enjoy a winery lunch today, a relaxing treat celebrating a fantastic trip together.

After wine tasting and lunch, we’ll continue north to Portland, arriving in time for evening flights or dinner in the city before more Oregonian adventures!

Walking Distances: 2 to 3 miles (350′ elevation gain)

– END –

Crater Lake Multi-Day Tour Additional Info

⭐ Admiring the extraordinary blue of Crater Lake from Watchman Overlook. Circumnavigating the historic Rim Drive chasing wildflowers and investigating unique volcanic remnants.

⭐⭐ Exploring the sights and history of Smith Rock while keeping an eye out for accomplished rock climbers. Following the shift in landscape from the mossy western slopes to the dry eastern valleys of the Cascades.

⭐⭐⭐ Refreshing mind and body in the restorative mists of Oregon's most treasured state park: Silver Falls. Meandering through lush, evergreen giants along the Trail of Ten Falls.

⭐⭐⭐⭐ Savoring the array of flavors found in a glass of Pinot Noir in the famous Willamette Valley. Indulging in winery lunches and brewpub dinners after satisfying days on the trails.

⭐⭐⭐⭐⭐ Dipping toes in the Deschutes River, sampling beers from the many craft breweries in town, and strolling through picturesque downtown Bend.

⭐ A TripAdvisor 'Hall of Fame' guide.

⭐ All entry fees.

⭐ Overnight accommodations both nights.

⭐ Local, organic picnic lunches - served outside when the weather is right.

⭐ All meals are included: 3 breakfasts, 3 lunches, 2 dinners

⭐ Pick up and drop off in downtown Portland.

⭐ Transportation throughout the tour.

⭐ Snacks, water, sparkling water, local wine, local adult beverages available throughout the tour.

McMenamin’s St. Francis School is 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.

Under Construction

Meals - Under Construction for 2020

Join us in exploring Crater Lake! Find your tour.

Book A TourAsk A Question

Other multi-day tours you might like:

3-Day Columbia Gorge National Scenic Area Tour

5-Day Columbia Gorge, Mt. Hood, Willamette Valley, Oregon Coast, and Portland Tour

Explore Multi-Day Tours From Seattle, Washington