Oregon Sea to Sky Cycling Tour – 9 Day Self-Guided

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Double Booking


Single Booking


Roommate Rebate


Includes all lodging reservations with breakfast, recommendations for dinner and lunch, luggage transfer for each tour day, tour maps, cue sheets and .gpx files, T-shirt, narratives about the area, 24x7 phone support on tour

Assembly Point

Hillsboro, OR


Arrive at: Portland International Airport, Portland, OR

Optional Add-ons:  Pre and Post Tour Lodging Arrangements

The Pacific West state of Oregon is one of the most diverse states in the country.  From sea level to towering Mt. Hood and from remote national forests to bustling cities, Oregon has it all.  Our Sea to Sky tour highlights this diversity.  You will experience the rugged coastline with its pounding surf and expanses of beautiful, sandy beaches, up to the timberlands of the Siuslaw, Willamette, Deschutes and Mt. Hood National Forests. You will cycle through the pastoral setting of the Willamette Valley and the vibrancy of Eugene. Your anticipation will build as you trace the McKenzie River in preparation for your assault upon mighty McKenzie Pass and the towering snowclad Cascades, and on to your approach on Mt. Hood for an unforgettable final night at the Timberline Lodge. Revel in the essence of this Sea to Sky experience.

For this challenging 9-day tour, you’ll ride 566 miles, starting along the Pacific coast, then inland through the “Emerald City” and onto the flanks of Oregon’s highest mountain.  Lodging will reflect the environment, from the family run ocean side retreat to the bustling urban hotspot near restaurants and downtown sights, to the historic alpine lodge next to the only year round ski resort in north America.

This area enjoys a long cycling season, from May through October. This tour can be booked for any dates in theat range, however one must be aware of McKenzie Pass.  Day 6 of the tour follows the secondary scenic highway over McKenzie Pass, which is closed in winter.  The pass is typically open from late June through October, but the opening date is dependent on snow depth, and has opened as late as August.  The alternative, but less scenic route will add 10 miles to that day’s ride.  Tours must be booked at least 2 weeks in advance, with a minimum of 2 participants.

(Note: actual hotels are subject to availability and not guaranteed before booking)


Day 1Hillsboro - Tillamook78
Day 2Tillamook - 3 Capes Scenic Route - Lincoln City64
Day 3Lincoln City - Newport - Florence77
Day 4Florence - Sand Dunes - Eugene66
Day 5Eugene - McKenzie River - Blue River56
Day 6Blue River - McKenzie Pass - Sisters46
Day 7Sisters - Detroit Lake56
Day 8Detroit - Timberline Lodge (Mount Hood)75
Day 9Timberline Lodge - Portland48

Total Distance: 566 miles

Oregon Sea to Sky Cycling Tour – 9 Day Self-Guided


(9 days, 8 nights)