For a decade and a half, our naturalist guides have been leading travelers through immersive experiences in the fantastic western landscapes highlighted on this tour. In our travel experiences, we’ve seen too many other travelers come to the Pacific Northwest and return home with boxes unchecked – trails, towns, meals, and destinations for which there just wasn’t time. We believe that time is the most precious travel commodity there is, so we’ve brought together as much of the Oregon ‘to-do list’ as possible into one single trip with dedicated time to explore the very best of the region.
We’ll leave plenty of time to reflect and relax, but with this tour, we want you to be able to take in as much as possible of the Portland region’s best in a single trip with no regrets, and no “I wish I could have’s…” when you return home – just the satisfaction of having used your travel days to the fullest!
Day 1: Columbia River Gorge National Scenic Area & Hood River
Waterfall Alley, Hood River Wineries, & Rowena Crest
Your journey begins just east of Portland as you enter the Columbia River Gorge National Scenic Area with less than a 30-minute drive. We’ll hit the trail at Latourell Falls in the morning, and make stops at two other waterfalls in “Waterfall Alley.” This will include a stop at the tallest in the region, Multnomah Falls. Your guide will share stories from the formation of the gorge to the many ways locals play here today, with plenty of scenery in between. Moss hangs from the trees, and cold mountain water tumbles down the rocks, with all of this natural beauty highlighted by the scenic highway.
Lunch will be served at a winery in the Hood River Valley, where warmer temperatures allow for a wide array of grape varietals to grace your glass. East of Hood River, there’s more scenic highway to explore, and the trip out to Rowena Crest Viewpoint highlights the climatic change this day brings – here, east of the Cascade Mountains, the landscape has changed dramatically, offering up a more austere and rocky scene of grasses, scrub oak trees, and ponderosa pines. Enjoy some free time this afternoon in Hood River before gathering together for a welcome dinner in downtown Hood River.
Walking Distances: 4 to 5 miles (1750′ elevation gain)
Accommodations: Hood River Hotel
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Day 2: Mt. Hood, Willamette Valley, & McMinnville
Mount Hood hiking, Timberline Lodge, Willamette Wineries, & more!
Today we climb! Making our way around the east side of Mt. Hood, there will be opportunities to stop for mountain views and a hike in the woods. After some good trail-time alongside mountain hemlocks and huckleberries, we’ll lunch in style at the historic, Depression-era Timberline Lodge at 6,000-ft of elevation and take a chance to explore the alpine landscape.
Descending from the famous lodge, we’ll skirt the edges of Portland to visit wine country in the Willamette Valley. Pinot Noir is king in this valley, as it’s the grape that put the region on the wine map, but there are plenty of other wines for all to enjoy before we settle into our overnight digs in downtown McMinnville.
Walking Distances: 2-3 miles
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Day 3: The Oregon Coast
The Coast Range, Tillamook Cheese, & the Pacific Ocean
This morning we’ll travel over the Coast Range – a noticeable shift from those mighty Cascades! – for our first encounter with the Pacific Ocean in the aptly named Pacific City. Along what’s known as the Three Capes Loop, we’ll have sweeping views of the ocean and a chance to hit the trails,or battle our way to the top of sand dunes!
We’ll stop in at the Oregon icon Tillamook Cheese Factory for tasty sample before heading north on famous Highway 101 around Nehalem Bay and up and over Neahkahnie Mountain, looking out over the endless ocean. Numerous state parks along this rugged section of coastline invite exploration as we near Cannon Beach, our home for the next two nights. We’ll have plenty of opportunities over the next two days to walk the beach, soak up a sunset, and stock up on saltwater taffy!
Walking Distances: 5 to 6 miles (900′ elevation gain)
Accommodations: Surfsand or Tolovana
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Day 4: The Oregon Coast
Cannon Beach, Ecola State Park, & Local Brews
We’re staying put in Cannon Beach today! Your guide will provide hiking options and plenty of local recommendations for a day of relaxation and discovery on the coast.
Get sand between your toes with a stroll to picturesque Haystack Rock or take a chance to walk in the footsteps of Lewis & Clark at Ecola State Park, where they traversed over Tillamook Head in 1805. A pub lunch may be your introduction to the region’s craft breweries, and galleries and shops offer plenty of coastal diversions for a leisurely day off the road.
Walking Distances: 3 to 5 miles
Accommodations: Surfsand or Tolvana
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Day 5: Urban Portland Exploration
City Touring, Hidden Gems, & Food Trucks
The final day of our adventure finds us traveling through the coastal forests back towards Portland! As we approach the city, we’ll delve into the history and local culture of Oregon’s metropolitan heart. We’ll stop for artisan donuts at a local institution and take advantage of Portland’s flourishing food scene with lunch at a “pod” of neighborhood food carts. After an enriching and delicious last day, we’ll go our separate ways. If you are continuing your travels with a stay in the city, we can drop you at your downtown hotel, or at the airport for those making their way home this evening.
Walking Distances: 1 to 3 miles
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5-Day Oregon Bucket List Tour Details
⭐ Traveling down the spectacular Waterfall Alley, exploring the towering falls that carry relentless rainfall into the vital Columbia River. Compiling a powerful, visual story of Oregon's incredible terrain riding the scenic highways from rivers to mountains and sea.
⭐⭐ Walking the Pacific Crest Trail around Mt. Hood among ephemeral wildflowers and waterfalls. Joining breathtaking Cascade Mountain views with delicious, farm-to-table cuisine at the Cascade Dining Room of Timberline Lodge.
⭐⭐⭐ Strolling among the ferns, hanging mosses, and towering trees of the coastal rainforest. Sampling tasty cheddars at Tillamook Cheese Factory as you make your way to the Pacific coast.
⭐⭐⭐⭐ Soaking up sunset over the Pacific Ocean with sand between your toes at Haystack Rock in Cannon Beach. Following in the footsteps of Lewis and Clark where they traversed Tillamook Head in 1805.
⭐⭐⭐⭐⭐ Chowing down on delicious bites that have made the Rose City famous for its food scene. Stopping to smell the roses - literally - at the International Rose Test Garden.
⭐ 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.
Meals - Under Construction for 2020