Route 66 Self Guided Motorcycle Tour - Harley-Davidson Museum

This is the full pilgrimage. Seventeen days, sixteen nights and around 2,520 miles, opening with a VIP day at Harley-Davidson’s own headquarters and museum in Milwaukee before riding the entire length of Route 66 from Chicago to the Santa Monica Pier.

The Milwaukee day at the start is the part no other tour in the range offers. The museum holds Serial Number One, the oldest surviving Harley-Davidson, alongside the archive and the factory operations, and the VIP access goes beyond the public visit. From there a short 93-mile ride along Lake Michigan reaches downtown Chicago, where the Mother Road begins.

What follows is Route 66 in full. Springfield, St Louis, the Missouri Ozarks, Tulsa, Oklahoma City, the long run into Amarillo, then two nights and a free day in Santa Fe. Gallup, Flagstaff and Williams follow with the Grand Canyon, then the best-preserved stretch of the old road through Seligman, Kingman and the switchbacks down to Oatman, before the Mojave and Victorville lead to Los Angeles and the pier.

EAGLERIDER supplies the motorcycle and books all sixteen nights, with Harley-Davidson touring models alongside Triumph and BMW sport machines. Fuel, meals and insurance are arranged separately. Riding days run from 93 to 290 miles, with a free day built in halfway. For a rider who has wanted Route 66 for years and would rather start at the factory gates than the city limits, this is the version to look at, and at seventeen days it is the longest self-guided trip EAGLERIDER runs anywhere.