I just learned that the Motorcycle Cannonball Run took place in Sept, was for 90 year old and older motorcycles, and went from Virginia to Oceanside (north San Diego)

https://www.facebook.com/motorcyclecannonball

On Thursday September 9th 100 riders will depart Sault Ste. Marie, Michigan and travel 4300 miles across America to end up in South Padre Island, Texas on Sunday, September 26th. Most of the route will be on two-lane back roads with less than 100 miles on interstate highways.

 

Held every two years on vintage motorcycles. Next event will be in 2021 as we travel from Sault Sainte Marie, MI to South Padre Island, TX on Pre 1930 Motorcycles

https://www.facebook.com/motorcyclecannonball/

A Maine to Oregon motorcycle Cannonball is underway, Portland to Portland

http://motorcyclecannonball.com/route/

since they are already on the road, and I only just learned of it, here's where you might see them passing through

September 13th 2018 Stage #6 Bourbonnais, IL to Anamosa, IA (National Motorcycle Museum)

September 14th 2018 Stage #7 Anamosa, IA to Spirit Lake, IA

September 15th 2018 Stage #8 Spirit Lake, IA to Pierre, SD

September 16th 2018 Stage #9 Pierre, SD to Sturgis, SD

September 17th 2018 Day Off Sturgis, SD

September 18th 2018 Stage #10 Sturgis, SD to Billings, MT

September 19th 2018 Stage #11 Billings, MT to Great Falls, MT

September 20th 2018 Stage #12 Great Falls, MT to Kalispell, MT

September 21st 2018 Stage #13 Kalispell, MT to Spokane Valley, WA

September 22nd 2018 Stage #14 Spokane Valley, WA to The Dalles, OR

September 23rd 2018 Stage #15 Grand Finale The Dalles, OR to Portland, OR

 Since the first Motorcycle Cannonball run in 2010, antique motorcycle riders from around the world have anxiously signed up to follow Lonnie Isam Jr. across the United States on a unique journey that many have described as life changing.

 Before his passing due to cancer in August of 2017, Lonnie had already passed the Cannonball torch to Jason Sims and had guided him through the rough patches of the 2016 iteration. Jason carries on the even numbered year cross country ride

http://motorcyclecannonball.com/about/

Jay and a 1912 Indian that did the Cannonball

there it is right in the center, after just crossing the finish line at the 2016 Cannonball

The Motorcycle Cannonball made it to the finish line in Carlsbad right on time, and there was a big crowd of family and supporters to meet, greet, and welcome them

proof that 100 year old motorcycles burn up quite a bit of oil internally and externally

1914 Warrick Motor Carrier

You've got 2 years to make ready a motorcycle over a 100 years old for the next Cannonball.... and it's seriously one of the coolest things you'll ever do. Bucket list or not.

During the trip, they passed through the Mojave Desert where it was 96 degrees, and entered the Joshua Tree National Park where it was 100 degrees.

update, Nov 2018
 https://www.guitarplayer.com/guitaraficionado/pat-simmons-goes-rockin-down-the-highway-on-a-vintage-harley

Doobie Brothers guitarist Pat Simmons and his wife, Cris set out to cross the U.S. on antique Harley-Davidsons,

His wife competed in the Cannonball alongside him, is a celebrated rider, journalist, and historian. Her many accomplishments include founding and editing the magazine Harley Women, authoring the 2009 tome The American Motorcycle Girls 1900–1950, and being inducted into the AMA Motorcycle Hall of Fame. At this year’s Cannonball, Cris, who rode a 1915 Harley-Davidson Model 11-J she nicknamed Effie, was the only female to complete the entire course. Pat did not fare as well riding a 1914 Harley two-speed nicknamed “Vinnie” (“after a buddy of mine who’s a unique individual,” he says with a laugh), started giving him a problem on the road and then it just came apart in Missouri

“We were on our way to Cape Girardeau in Missouri,” he recalls. “Basically the engine stopped. Parts had come off and lodged in the gear chain, broke a number of my gears, and basically froze the engine. It wouldn’t even turn over at that point. It was nothing I could have predicted. When you’re on a 102-year-old bike, you just never know what can happen.”