Oregon Sea to Sky

Oregon Sea to Sky

July 4 - 13, 2018

(10 days, 9 nights; Wed - Fri)

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Double Booking


Single Booking


Roommate Rebate


Includes all lodging, breakfasts and dinners, support van, transfers, leaders, tour maps and narratives.

Assembly Point

Hillsboro, OR

Timberline van shuttle is included between Portland and Hillsboro prior to and following tour.

Not Included: Airline Service to Portland International Airport; Guide Gratuity.

Meeting Time

Airport 3 pm, Hotel 3:30 pm

Drop-off Time

5 pm

The rugged Oregon Coast, the pounding surf and expanses of beautiful, sandy beaches, the timberlands of the Siuslaw, Willamette, Deschutes and Mt. Hood National Forests, the pastoral setting of the Willamette Valley; the vibrancy of Eugene; the anticipation that builds as we trace the McKenzie River in preparation for our assault upon mighty McKenzie Pass and the towering snowclad Cascades, our “day in the wilderness” as we approach Mt. Hood and an unforgettable final night at the Timberline Lodge. The litany of experiences goes on and on—this is the essence of the Oregon Sea to Sky. Our cycling tour assembles in Hillsboro, just west of Portland, and we ride to Tillamook on Day 1, where we’ll visit the famous Tillamook Cheese factory. The next two days belong to the Oregon Coast. We’ll follow the Three Capes Scenic Route southward through Cape Mears, Lookout and Kiwanda and on to our overnight in the oceanside community of Lincoln City.

Our ride along the coast continues to Florence on Day 3, as we pass through the progression of state parks, created to protect the entire length of the Oregon Coast, and the many quaint coastal villages along the way. We’ll overnight on the ocean at the Driftwood Shores Resort, visit the Sand Dunes outside of Florence the following morning and then turn east for our gentle climb over the Coastal Range. Our fourth night is planned for Eugene, site of the University of Oregon, as we prepare for our transition from the sea to the sky.

It’s on to the Cascades on Day 5 as we trace the course of the McKenzie River to its source among the high peaks to the east. A relaxing evening in the cozy setting of the historic Holiday Farm precedes our engagement with McKenzie Pass on Day 6. McKenzie Pass is one of the West’s great alpine challenges. The grade on this climb, though long, is gradual and not intimidating. The emphasis here is the opportunity to absorb the spectacular variation in terrain that we encounter along the way. From the banks of the McKenzie, we climb through the heavily timbered Willamette Forest to the famous Belknap Crater and extensive, almost other-worldly lava fields and observatory atop McKenzie Pass. A spectacular descent precedes our overnight in Sisters. From Sisters, it’s on to Detroit and an overnight on the shores of Detroit Lake. Early-morning of Day 8, we’ll ride the paved network of forest roads through a semi-wilderness area to the base of Mt. Hood, where we’ll spend our final night at the historic Timberline Lodge. Our return to Portland is virtually a downhill cruiser for much of this final day.



Day 1Assembly, bike fitting, orientation
Day 2Hillsboro - Tillamook78
Day 3Tillamook - 3 Capes Scenic Route - Lincoln City64
Day 4Lincoln City - Newport - Florence77
Day 5Florence - Sand Dunes - Eugene66
Day 6Eugene - McKenzie River - Blue River56
Day 7Blue River - McKenzie Pass - Sisters46
Day 8Sisters - Detroit Lake56
Day 9Detroit - Timberline Lodge (Mount Hood)84
Day 10Timberline Lodge - Portland48

Total Distance: 569 miles

Inn Highlights

Oregon Sea to Sky

July 4 - 13, 2018

(10 days, 9 nights; Wed - Fri)