7 nights/ 8 days
Portland to Portland

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Oregon’s landscape is diverse with a windswept Pacific coastline, a volcano-studded Cascade Range, and abundant bodies of water in and west of the Cascades, combined with dense evergreen forests at lower elevations and a high desert sprawling across much of its east all the way to the Great Basin. North America’s deepest lake and the purest large body of water in the world, Crater Lake, can also be found here. On this 8-day multisport adventure, we’ll hike, bike, and kayak as we explore its unparalleled diversity in landscapes and beauty. Get set for big-time fun in the Pacific Northwest and discover why Oregon is a destination worthy of exploration!

2017 Dates:July 22-29 $1995 (Single Supplement $610)
Trip Leader(s):Stacey
Places Visited:Portland, Willamette Valley, Eugene, McKenzie River National Recreation Area, Crater lake National Park, Bend, Cascades Lakes, Columbia River Gorge
Activities:Hiking, Biking, Kayaking, Cave Exploring
Group Size:Min. 6 Max.12 people
Travel Style:Comfort
Physical Rating:Easy to Moderate

Ready to book? Please click the button below to BOOK THIS TRIP and submit your information along with a $250 deposit.  Your deposit is fully refundable for 72 hours and always transferable to any of our other trips, or we can hold it for a future trip.

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  • Discover why Portland is known Bike City USA
  • Explore the largest urban forest in the United States
  • Relax in the soothing warm waters of the Terwilliger (Cougar) Hot Springs
  • Explore Oregon’s magnificent waterfalls
  • Discover the blue waters of Crater Lake National Park, the deepest lake in America and one of the 7 Wonders of Oregon
  • Kayak on the glassy water of Cascade Lakes surrounded by the Three Sister, Broken Top and Paulina Peaks
  • Explore the inside of a lava tube cave
  • Stay in a converted 1930’s school house complete with a pub, brewery, a move theater, live music venue, and a fantastic soaking pool
  • See why US Congress recognizes the Columbia River Gorge as a National Scenic Area and why it’s one of the 7 Wonders of Oregon


Day 1: Portland

Today is arrival day and there are no planned activities, so you are free to arrive in Portland at any time. Upon arrival, you will be picked up by your trip leader and taken to your hotel for the night. You’ll have the rest of the day free to explore the city on your own and possibly check out some of the city’s incredible breweries, restaurants, and the local music scene. Portland has 145 square miles of exciting things to do, eat, drink, see, hike and explore.

–Airport Pickup

Overnight at Mark Spencer Hotel

Day 2: Portland (B)

Portland is known as Bike City USA, probably for its 315 miles of bikeways, or possibly for the nation’s highest percentage of bike commuters. Today, we’ll spend the day exploring these bikeways. The Waterfront Loop leads you along Portland’s meandering Willamette River, through Oaks Bottom Wildlife Refuge, and then back along the westside of the waterfront. This loop offers one view after another of the Willamette River and the surrounding greenspaces. Mostly on paths, with just a few short sections on streets, this is a delightful and relaxing ride. Take the side trip over to Tideman-Johnson Park if you’d like a little more distance.

The Forest Park Conservancy covers 5,157 acres and is one of the largest urban forests in the United States. There are 30 miles of bikeable paths in Forest Park, with the most popular route being the 11.2-mile Leif Erikson Drive, with views of the Columbia River, Mount Hood and Mount St. Helens. With more than 80-miles of soft-surface trails, fire lanes and forest roads, Forest Park offers ample opportunities for hiking, running, biking, walking, and simply escaping the urban atmosphere. An abundance of wildlife can be found in Forest Park and the 30-mile Wildwood Trail is part of the region’s 40-mile Loop trail system that links Forest Park to pedestrian and trail routes along the Columbia River to Gresham, through southeast Portland, along the Willamette Greenway, and back to the Marquam Trail in southwest Portland.

Portland is an incredible city and worthy of a full day of exploration.


— Multi-Speed Bicycle Rental (24 hours)

Overnight at Mark Spencer Hotel

Day 3: McKenzie River National Recreation area/ Eugene (B) 

Today, we’ll head south to Eugene for some hiking and waterfall exploring! Our first stop will be the McKenzie River Waterfall Loop Trail to see Sahalie Falls and Koosah Falls. This is a 3-mile trail at 2800ft elevation and is part of the McKenzie River National Recreation Area. It follows the McKenzie River as it flows over two spectacular waterfalls and cascades into whitewater.

From here, we’ll continue to Proxy Falls, one of the streams cascades into two separate shimmering veils dropping 226 feet. It’s two of the most unique waterfalls in Oregon and among the most frequently photographed. It’s an easy to moderate 1.5-mile loop to see both falls.

Afterwards, we’ll soak in the natural mineral waters at Terwilliger (Cougar) Hot Springs. As you walk the ¼ mile trail to this clothing optional hot springs, you are enveloped in the dark hues of primeval woodland, touched by mottled light filtering down from treetops high above and the invigorating scene of the lagoon and the gorgeous Rider Creek waterfall spilling into it. Six tranquil pools are spaced apart by rock walls laid out in steps down a ravine. Temperatures range from 85 degrees in the lower pool to 112 degrees in the upper pool. The pools are 3-12 feet across and an average of 2-3 feet deep. The pool floors are mostly bedrock but some gravel, sand and debris remain at the bottom of the pool.

This evening, we’ll spend the night in Eugene, a diverse and friendly city in the south end of the Willamette Valley between two small buttes, and beside the scenic Willamette River.


— McKenzie River Waterfall Loop Trail (2.6 mile loop, 400ft elevation gain)
— Hike to Proxy Falls (1.5 miles, easy)
— Visit Terwilliger (Cougar) Hot Springs

Estimated travel time: 4.5 hours
Overnight at Valley River Inn or similar

Day 4: Crater Lake National Park (B)

There’s a legend in Oregon that when the first Crater Lake visitors with color cameras took their photos to be developed, they were reimbursed for what Kodak assumed was an error in the printing process. Little did Kodak know, the impossibly bright blue hue of Oregon’s Crater Lake was, in fact, real. From high atop the rim of Crater Lake, you can see what a wonder the world really is. A hike down to the water reveals new wonders. The water is so blue, so deep, it’s no surprise it’s the deepest lake in America, and one of the deepest on earth. That’s why it’s one of the 7 Wonders of Oregon.

Surrounded by cliffs almost 2,000 feet high and boasting a picturesque island, Crater Lake was established as a national park in 1902 and it’s the fifth oldest in the United States. It encompasses 183,225 acres and there is lots to do here from boat tours, hiking, or just relaxing.

The rest of the day will be a free day, at your leisure. There is more than 90 miles of hiking trails, ranging from easy to strenuous. Additionally, thirty-three miles of the Pacific Crest Trail pass through the park, offering hikers magnificent views of the lake.  Due to the elevation of the park (6,500ft to 7,100ft), weather conditions may change quickly and a warm jacket and wool sweater are always recommended items to carry, even in the summer.

Estimated travel time: 2.5 hours
Overnight in a Vacation Rental

Day 5: Cascade Lakes/ Newberry National Volcanic Monument/ Bend

This morning, we’ll journey into the mighty Cascade Range to paddle the glassy waters of a spectacular mountain lake. Be sure to watch for otter, mink, osprey and eagles, and bring a camera for the best mountain views in Central Oregon! We’ll spend over 2 hours on the water to soak in the surrounding natural beauty. Wear your swimsuit for a refreshing dip! You’ll see parts of these large lakes that are only accessible by paddling into the fingers, coves, bays, and wetlands created by ancient eruptions and erosion. Surrounded by the Three Sisters, Broken Top, or Paulina Peak, kayaking provides the ultimate experience in this area.

On our way to Bend, we’ll stop at Newberry National Volcanic Monument and explore the inside of a lava tube on this subterranean trail. A full mile long, this self-guided tour runs through an incredible environment and geology. Average temperature in the cave is 42 degrees, so dress accordingly.

This evening, we’ll explore some of the local breweries in Bend. In this little mountain town of more than 87,000 people, Bend has more breweries per-capita than any other city in Oregon and has been dubbed Beer Town USA! If beer isn’t your thing, that’s okay. Bend’s growing selection of distilleries and wineries are a great way to quench your thirst for adult beverages.


— Kayaking Tour at Cascade Lakes
— Visit to Lava River Cave

Estimated travel time: 1.5 hours
Overnight at McMenamins Old St. Francis School

Day 6: Bend

Central Oregon has some of the most spectacular and beautiful hikes in the country, if not the planet. In continuing with our chasing of waterfalls, today we’ll see the most popular waterfall located within the Bend city limits, the nearly 100-foot Tumalo Falls. A short jaunt will bring you past views of the waterfall, located along Tumalo Creek, but continue to the top of the falls and follow a wonderful trail system to Double Falls and Upper Falls and then North Fork Falls, and Spring Creek Falls to complete the 7-mile loop.

This evening, we’ll enjoy more of this vibrant, hip, cosmopolitan mountain town and possibly head to the Old Mill District for dinner and a walk along the Deschutes River.


— Hike Tumalo Falls Loop (7.1 mile loop, 1312ft elevation gain)

Overnight at Overnight at McMenamins Old St. Francis School

Day 7: Columbia River Gorge/ Portland (B)

As we make our way back to Portland, we’ll discover Multnomah Falls and dozens of other falls like Horsetail, Ponytail and Bridal Veil along the Historic Columbia River Highway. Carved by the great Missoula Floods, the Columbia River Gorge is a stunning landscape full of breathtaking vistas and abundant waterfalls. Touring the Gorge is easily one of the most scenic routes you can take in all of Oregon. With its charming orchards and vineyards and Hood River’s laid-back, surf-town vibe, the area seems like another world, though it’s only an hour from downtown Portland. Thanks to its unique geography, US Congress recognized the unique splendor of the Gorge and designated it a National Scenic Area, the largest in America. And when you see if for yourself, you’ll understand why it’s one of the 7 Wonders of Oregon.


—Visit Multnomah Falls, Horsetail, Ponytail and Bridal Veil Waterfalls

Estimated travel time: 4 hours driving
Overnight at Mark Spencer Hotel

Day 8: Portland/ Departure

Today is departure day and there are no planned activities. If you have time, you can tick-off any last minute shopping you might like to do before your departure.


—Airport dropoff

What’s Included?

7-nights hotel
All meals indicated in the itinerary (B=Breakfast, L= Lunch, D=Dinner)
Van transportation for all included activities & airport transfers
Portland Bicycle Rental
Proxy Falls Permit
Kayak Tour at Cascades Lake
Hiking – McKenzie River Waterfall Loop Trail
Hiking – Proxy Falls
Hiking – Tumalo Falls Loop
Visit Terwilliger (Cougar) Hot Springs
Visit Multnomah Falls, Horsetail, Ponytail and Bridal Veil Waterfalls
Visit to Lava River Cave

What’s Not Included?

Airfare to/from Portland Airport (PDX)
Beverages & Meals not specified
Optional Activities
Gratuities for your local guides
Personal Expenses
Travel Insurance
Airport taxes and excess baggage fees


The information in this trip details document has been compiled with care and is provided in good faith. However, it is subject to change, and does not form a contract between parties. While it is our intention to adhere to the route described, there is a certain amount of flexibility built into the itinerary and on occasion it may be necessary, or desirable to make alterations. The itinerary is brief, as we never know exactly where our journey will take us. Due to our style of travel and the regions we visit, travel can be unpredictable. Occasionally our itineraries change due to weather or other circumstances that are beyond our control. Additionally, any travel times listed are approximations only and subject to vary.