The Loop 2026: A Vintage Motorcycle Ride to Remember
by Michael Stieber, Marketing Field Manager
As long as I can remember, I have been amazed and intrigued by the riders and machines of the Motorcycle Cannonball or Cross-Country Chase events, endurance-style motorcycle racing on vintage machines. Participating in one has been an ultimate bucket-list item of mine for years.
Enter The Loop
Around November 2025, I heard of an opportunity to enter a five-day motorcycle endurance race on 1930–1959 motorcycles. Being a weeklong event, versus three-plus weeks on the cross-country rides, I found this to be doable.
What to Ride?
A friend of mine has a 1947 Knuckle and a 1948 Pan, so I broached the subject of riding those on the ride. He agreed, and we signed up.
A few weeks later, my friend backed out, and here I was, entered in my dream race with nothing to ride.
It was then that I scoured sources online and found a 1959 BMW R50 with 7,800 miles. It was in Connecticut. A friend of mine from the Mobile Bay Vintage Motorcycle Club was going to visit some family up that way and said he would look at the bike and purchase it for me.
I received the 1959 BMW R50 in December 2025. As The Loop wasn't until September 2026, I was not in a rush to get it working and running. I had plenty of time. (LOL.)
The bike was complete but had been sitting. It didn't take much to get it going. Right away, the coil was upgraded and a new light switch was put on. After some more cleaning and going through the bike, it fired up!
By now, several months had passed. I took the BMW for about a 40-mile ride, and it started showing some issues. One was that it was leaking oil badly. We replaced the rear main seal, throwout bearing seal and kickshaft seal.
An important lesson was learned later that should have been learned here.
The bike was also showing charging issues. We replaced the voltage regulator, ignition advance, condenser, carb insulators and gaskets.
After this, the bike was running OK, but we did some more tuning and adjusting. When we finally got it right, one week before the ride, we found out the clutch was slipping due to failure of the transmission seal.
This was the lesson mentioned earlier: Since the bike was already apart, I should have replaced that seal with the others.
But instead, here I was with the bike and transmission apart two days before leaving on the trip.
We buttoned the bike up on a Friday, and Saturday morning I was off to Chattanooga to begin a ride of a lifetime!
The Ride Begins
From the first person I met, a former Cannonball participant, every single person in attendance was absolutely amazing. There were so many gorgeous bikes from 1930–1959.
We departed Monday morning, Labor Day, for parts unknown. All we knew was that we were going to be riding 150–200 miles a day. We were given a roll chart every morning with our directions.
What ensued was five days of riding utterly amazing roads with 60 of the best vintage motorcycle riders from across the country and even the world, including Canada and New Zealand.
A guy from North Carolina said after the ride that he has been riding the roads of the area for over 50 years and had never had a more technical, challenging or fun time than on this ride!
There were Sturgis Motorcycle Museum and Hall of Famers present on the ride, including Berry Wardlaw, Tony “Pan” Sanfelipo and Vicki Roberts Sanfelipo. Bill Page, the organizer and known as the “Harley Whisperer,” has built four Sons of Speed champion race bikes. Sean Jackson and Tom Banks of Competition Distributing were there, along with many, many more!
Friendships were forged and memories were made on this amazing trip.
800 Miles Through Six States
Over five days, we rode about 800 miles through six states: Tennessee, Georgia, South Carolina, Kentucky, Virginia and North Carolina.
Most of the ride was in second or third gear, and I was in first gear more than fourth!
It was tight, technical, challenging back roads with hairpins, switchbacks, lots of sweepers, dirt mountain roads and even two creek crossings.
The Loop will once again be run in 2028 and will be leaving from New Mexico. All who participated in the first one were given spots in 2028 if they wanted them.
I think everyone signed up.
I know I did!
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