06/13/2026
We are enjoying the 2026 Tour season and looking forward to riding with you!
2026 Tour Dates - more forming - contact us for other not listed tours - BOOKING 2026 Now! - 2027 dates are the same or close to 2026 dates
The Loneliest Highway 50 coming for 2026
2 week trip San Francisco, Nevada, Colorado, on the loneliest highway, to Washington, D.C. Coast to Coast.
A little like Route 66 but not commercial or touristy, with less traffic and more mountains and other natural sights but not the commercial places you have heard of. Very authentic USA.
May early or mid June Music Tour
New Orleans, Nashville, Tail of Dragon, Atlanta, even a Texas option
dates tba
https://ridefree.com/american_motorcycle_music_tour
Discover blues and country music, and the real traditional America
May 19 - June 4 2026 - 17 Day Route 66 Chicago to LA - Guided Motorcycle Tour
https://ridefree.com/route-66-motorcycle-tour
Milwaukee Harley Museum pre trip optional extra.
A 17 day Rt 66 tour is so much more relaxed than any company's 15 day trip.
Note that all tour company's riding days are 2 less days than total days with the start and end day, so a 15 day is only 13 riding days which is not enough.
June 10-26, 2026 if it is the 17 Day Guided Tour - Route 66 Chicago to LA
https://ridefree.com/route-66-motorcycle-tour
Milwaukee Harley Museum pre trip optional extra
A 17 day Rt 66 tour is so much more relaxed than any company's 15 day trip.
Note that all tour company's riding days are 2 less days than total days with the start and end day, so a 15 day is only 13 riding days which is not enough.
May, June, July 2026 MUSIC TOUR - dates TBD
New Orleans to Milwaukee, New Orleans to Atlanta with Tail of The Dragon, and more
https://ridefree.com/american_motorcycle_music_tour
Discover blues and country music, and the real traditional America
June 12-20 2026 - California, Rt 66, Death Valley, Grand Canyon Motorcycle Tour- LA to LA
https://ridefree.com/route66_tour
June 20-29 2026 - California Dreaming Coast Guided - LA to LA -
https://ridefree.com/california_motorcycle_tour
Or
Wild West I - LA to Vegas June 13 -21, 2026 - 9 day
Wild West II - Vegas to LA June 20 to 28, 2026 - 9 day
or Combo - LA to Vegas, Vegas to LA - 16 Day June 13 - 28, 2026 https://ridefree.com/california_grand_canyon_route66
See the iconic Western Parks and Landscapes and the spectacular California coast.
July 2026 Canadian Rockies Guided Tour
https://ridefree.com/canadian-rockies-guided-motorcycle-tour
Stunning ride with breathtaking nature.
2026 MUSIC TOUR to Harley Milwaukee Homecoming Festival
I have my music tour on my website as a 14 day Itinerary Chicago to New Orleans, but can flip and tweak to be a 13 day music tour New Orleans to Milwaukee for the Start of the July 9 - 12, 2026 Harley Homecoming Festival - we can book the Homecoming Festival for you also
https://ridefree.com/american_motorcycle_music_tour
July 2026 MUSIC TOUR - 13 day New Orleans to Milwaukee to the Harley Homecoming Festival in Milwaukee
- or add Jack Daniels and more layovers for a 16 Day Ultra -
July 29 - Aug 12, 2026 - 15 Day - STURGIS Guided Motorcycle Tour - Denver to Denver
Has 4 nights in Sturgis Area and a West Yellowstone stop, so plenty of time in the Yellowstone area.
Option to also arrive in Sturgis early on arrival day, and leave Sturgis later on departure day, if you want even more Sturgis area time.
https://ridefree.com/sturgis_tour
86th Sturgis Rally, August 7 – August 16, 2026
This is one of the most scenic tours we do. The ride to Sturgis is amazing, and rides around Sturgis in The Black hills are also. Even if you don't partake in Sturgis activities, it is an amazing ride.
July 29 - Aug 10, 2026 - 13 Day - STURGIS Guided Motorcycle Tour - Denver to Sturgis, fly out Rapid City
Same as our 15 day above, but you fly out of Sturgis / Rapid City the morning we head towards Denver for our last few days. https://ridefree.com/sturgis_tour
July 29 - Aug 7, 2026 - 10 Day - STURGIS Guided Motorcycle Tour - Denver to Sturgis, fly out Rapid City
Same as our 13 day above, where you fly out of Sturgis / Rapid City.
The group arrives to the Sturgis area on Aug 6 in the afternoon and you say goodbye to the group after dinner. https://ridefree.com/sturgis_tour
The next day you fly out of Sturgis / Rapid city or you are on your own for your time in Sturgis. We can arrange for you to keep the same bike rental for your time in Sturgis until you are done, and arrange your hotels if you like. Or even give you our Self Guided Sturgis Tour info. But you will be on your own.
Denver to Yellowstone to Sturgis to Indian Bike Week to Milwaukee
12, 16, and 19 day option on same tour - Similar to the Sturgis Tour but we end up in Milwaukee, with an option to go to Indian Bike Week after Sturgis.
12 Day - July - Aug 2026- Denver, Yellowstone, Sturgis
16 Day - July - Aug 2026 - Denver, Yellowstone, Sturgis, skip Indian Bike Week, Milwaukee
19 Day - July - Aug 2026 - Denver, Yellowstone, Sturgis, Indian Bike Week, Milwaukee
July - Aug 2026 - 17 DAY - STURGIS - Chicago or Milwaukee /Sturgis / Monument Valley, Grand Canyon / Rt 66/ Vegas or skip Grand Canyon Rt 66
then 15 Day July -Aug 11, 2026, after Monument then Zion then Vegas
- 4 nights Sturgis area plus 1 morning
- 86th Sturgis Rally, August 7 – August 16, 2026
https://ridefree.com/sturgis-motorcycle-tour-chicago-to-las-vegas
Aug 10 Day Tour - POST STURGIS - DENVER TO VEGAS VIA Million Dollar Highway, Monument Valley, Grand Canyon, and Route 66
August 2026 Canadian Rockies Guided Tour
https://ridefree.com/canadian-rockies-guided-motorcycle-tour
Aug 19-28, 2026 San Francisco to LA Guided Wine Tour - 10 Day Guided Motorcycle/Car Tour - add a day if want a layover in Napa, not just 1 night
A mix between these 2 tours on the site
https://ridefree.com/san_francisco_to_la_tour The San Fran to LA tour,
combined with some of our longer Wine Tour stops
- https://ridefree.com/california-motorcycle-classic-car-wine-tour-city
Much shorter riding days, a very relaxed trip. Great trip if you want a mellow trip. Even if you do not drink, this is a relaxed and fun scenic ride with plenty of time to enjoy the areas since we arrive early each day.
August 30 - Sept 14 2026 CA/NORTHERN CA 16 DAY GUIDED
https://ridefree.com/california-northern-motorcycle-tour
Enjoy the remote parts of California though the mountains and the less traveled Northern Coast and giant redwood trees.
Sept 14 - Sept 30, 2026- 17 DAY GUIDED TOUR Chicago to LA
https://ridefree.com/route-66-motorcycle-tour
Milwaukee Harley Museum pre trip optional extra
A 17 day Rt 66 tour is so much more relaxed than any company's 15 day trip.
Note that all tour company's riding days are 2 less days than total days with the start and end day, so a 15 day is only 13 riding days which is not enough.
August, Sept or Oct 2026 - Fall Music Tour with Tail of the Dragon, even a Texas option
https://ridefree.com/american_motorcycle_music_tour
dates to be announced
Discover blues and country music, and the real traditional America
October 2026 Wild Wild West I - LA to Vegas October 2026 Wild West II - Vegas to LA or Combo
exact dates to be announced
Wild West 1 and 2
Oct 2- 17, 2026 Combo - 16 Day
https://ridefree.com/california_grand_canyon_route66
See the iconic Western Parks and Landscapes and the spectacular California coast.
or California, Rt 66, Grand Canyon, Death Valley Motorcycle Tour
Oct 2 - 10, 2026 - 9 Day
https://ridefree.com/route66_tour
and California Dreaming Coast Tour
October 10 - 19, 2026 California,Yosemite, and Coast Guided
https://ridefree.com/california_motorcycle_tour
California Motorcycle Tour ,California Pacific Coast Highway Big Sur Yosemite Sierra Nevada's Harley Motorcycle Tour
