Self-guided Cycling Tours

Self-Guided Cycling tours include hotel reservations, routes with maps and cues, and luggage transfer when needed.  Pre and Post-tour hotels are not included.  Choose your own dates, within the season available.  Tours must be booked a minimum of 2 weeks in advance.

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

9 Days – [Portland – Florence – Eugene – Mt. Hood] From the pounding surf of the Oregon Coast to the flanks of Mt. Hood, you will discover the beauty of western Oregon.


Colorado High Country Cycling Tour – 10 day Self-Guided

10 Days – [Boulder – Steamboat – Vail]
Ride the Rockies over Trail Ridge Rd, through world-renown ski towns, over mountain passes and across high alpine parks. This tour can be shortened to 6 days.


Santa Barbara Cycling Tour – 5 Day Self-Guided

6 Days – [Santa Barbara – Solvang]
Cycle through the legendary Santa Barbara area to find the best of California biking. Vineyards, coastal riding, valleys and mountains – this has it all.


Kentucky Blue Grass Cycling Tour – 6 Day Self-Guided

6 Days – [Lexington – Berea – Bardstown – Lexington] Stay in country B & B’s and enjoy moderate cycling past famous horse farms and historic sites, among the rolling hills of Blue Grass and Bourbon country.


Latest Bulletin Board Post

  • Barbara Hoyt on Tour Discussion Board: “Our 2025 calendar is getting filled. Check back often to see what new tours we are including.Jul 6, 17:23
  • Alex Goerner on Tour Discussion Board: “Registration for Timberline’s 15th Annual C2C Adventure is now OPEN! Take advantage of our biggest discount for the 2025 tour…May 1, 14:03
  • Barbara Hoyt on Tour Discussion Board: “Thinking of a tour not on our calendar? Post your interest here, as others may have the same idea. We…Jan 26, 11:22
  • Barbara Hoyt on Tour Discussion Board: “Give the Gift of Adventure! Gift Cards Available Now Timberline Gift CardDec 5, 10:15
  • Barbara Hoyt on Tour Discussion Board: “Our October Special is in full swing! $300 off a 2024 tour. Use code EARLYO24.Oct 9, 11:23