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2025 Motorcycle Cannonball Candidate: 1926 Indian Chief

As I write this, 77 intrepid riders are riding vintage motorcycles across the United States competing in the 2023 Motorcycle Cannonball.  This biannual event is limited to motorcycles manufactured up to 1933 with limited modifications for the two-week plus trip.  Sound like your kind of party?  Well, it is too late to get in on this year’s festivities.  However, this 1926 Indian Chief, complete with a sidecar, is for sale on eBay in Spokane, Washington.  Mostly complete but obviously not in running condition, this vintage Chief is the perfect starting point if you want to brave the elements the next time the event crosses the country in 2025.  While this seems like an adventure of a lifetime, does the current bid of $20,100 or the Buy It Now price of $40,000 cool your ardor for adventure?

This year’s race is running from Virginia Beach, Virginia to Oceanside, California.  This roughly 3,800-mile jaunt would be a piece of cake for a modern touring motorcycle.  However, things were not all that luxurious or reliable in the years leading up to 1933.  The road system we know today was largely nonexistent.  Roads that were in place were mainly evolutions of the hunting paths and wagon trails of days gone by pressed into service and improved as needed.  Only a small percentage were paved, and most of that was in brick.  As for motor vehicles, the rapid march of technology from the turn of the century was impressive, but nearly every form of wheeled transportation at the time still had top speeds below eighty miles per hour and brakes to match.

Motorcycles were also suffering from growing pains.  The pre-Depression market was filled with several domestic makers.  Some, like Crocker and Excelsior-Henderson, offered some amazing vehicles for the time.  Others were little more than bicycles with one-cylinder motors similar to those used in the washing machines of the time.  The two giants of the motorcycle industry were Harley-Davidson and Indian.  Their rivalry was one of legend, both on the sales floor and on the racetrack.  That competition and the resulting improvement of both brands went a long way towards making sure they were the only two sizeable motorcycle manufacturers to survive the Depression.  Financial conditions and a limited market worked to thin the heard by the time World War II arrived.

Indian’s premier model was the Chief.  With a large (for the era) displacement V-twin engine and a comfortably large chassis, the Chief was a very desirable motorcycle among folks who wanted a motorcycle more for sport than transportation.  The Indian Chief you see here was made in 1926 and is a good study as to where motorcycle technology was at that time.  Notice the leaf spring front end, primitive electrical system, and fuel tank nestled inside the frame rails.  According to the listing, the engine displacement is 74 cubic inches.  If this is correct, then this bike came with the “Big Chief” option that would later be with the Chief as standard equipment until the brand’s demise after the war.  Having this option makes sense if the sidecar you also see in the pictures came with the motorcycle from the factory.  Regular Chiefs made do with 61 cubic inch engines.

So, what should you do if you want to go on this great adventure when it rolls around again in 2025?  My suggestion is to start early finding and preparing the best machine you can that fits within the rules.  Those rules call for a motorcycle manufactured in the year 1933 or earlier that has to be nearly all stock.  Allowances for safety and internal changes are permitted within reason.  What does this nearly complete Indian Chief offer to the prospective racer?  A large engine for the era, a long production run for that engine ensuring that parts are available, and the fact that it was one of the fastest motorcycles of its time period.  If restored with an eye for making a competent race bike, this Indian could be just the ticket for a reliable and relatively stress-free run across the good old US of A.

Yes, going on this adventure will take a lot of time, effort, and folding money.  However, this is a bucket list-level event if you are a motorcyclist and/or a history buff.  You can’t take your riches with you and your heirs will probably waste whatever you leave them on investments and other boring things like that.  Why not start preparations now for 2025?  They can sell the Indian when you are gone.

Would you be up for running the 2025 Motorcycle Cannonball?  Would this Indian Chief be your preferred ride, or do you have some other form of motorcycle madness in mind?  Share your thoughts in the comments.


  1. Howard A Member

    While my interest in these,,,antiques,,, is limited, one cannot ignore, in the 20s, this was the ultimate in personal transportation. Automobiles were clumsy, poor handling vehicles, and a motorcycle was very similar to a horse. Fact is, many bikers are still considered modern day cowboys, or girls. With the shenangians to match. I couldn’t imagine riding one any significant distance,,,which brings me to my connection with this post. The “Cannonball” came through my little town Monday in the Rockies. I got gas at my usual place, and noticed a bunch of vintage bikes also getting gas. Groups of special vehicles come through all the time, and I didn’t think much of it, until I asked the cashier, what gives? They all had a number affixed to the side, and he said, they are going cross country,,,for some reason. The “Rollin thru the Rockies” some pictures are from my hometown. One guy on a vintage BMW, having trouble “round back”, he had the carbs apart, with a puddle of gas, and working with a freakin’ adjustable wrench, didn’t look too happy. I offered my help, but he said he had plenty, and a “chase trailer” was close behind. IDK, this guy, well, all of them really,, looked horribly unprepared for something like that, on those machines. After my latest cross country trip in an air conditioned Kia, I couldn’t imagine it on one of these. Best of luck to them, I hope the guy got his BMW going, looked like a lot of fun. Oh,, the rich and famous,,,on a Monday,,,

    Like 13
    • J Sparks

      I caught the Motorcycle Cannonball at Speedway Harley-Davidson in Concord, North Carolina – it was the destination of the first leg from Virginia Beach. I wish I could have looked at every machine! The variety of interesting old motorcycles they’re riding is vast. I spoke with a rider from Hungary who brought his Hungarian-made motorcycle across the Atlantic to ride across the United States. With only paper maps. The vibe was very positive as riders rode into the parking lot on day one! I’ve been wondering how it’s going, and how the guy on the orphan Hungarian moto is doing.

      Like 6
      • J Sparks

        Correction – Greenville to Concord was the second stage. Speedway H-D was the second leg destination.

        Like 1
    • geomechs geomechs Member

      Well, the minute I saw this I wasn’t thinking about any cross-country adventures. I rather thought of Cycletoons and the Adventures of Hogg Ryder” and the “Ol’ Poop” on his ‘26 Indian. The ol’ Poop was always getting the upper hand (and the girls) over Hogg Ryder. Well, that’s okay; Cycletoons kept me entertained for many years.

      Now, back to this, I would love a bike like this, although without the sidecar. I would love to fix this up and ride it. I could be a for-real ol’ Poop on his ‘26 Indian…

      Like 2
  2. Chris Cornetto

    A very neat impractical sonar blip. All kidding aside this will make a helluva museum piece. For me I’ll stay on my Hyabusa, I cannot imagine riding this any kind of distance. The Conestoga wagon of motorcycles. This will likely hit its buy it now before it ends. There are lots of collectors with deep pockets and few of these and the side car is a BIG plus.

    Like 2
  3. Troy

    Wow, brings back memories. Grandpa had one like that in about that condition leaning up against a post in the barn as I was growing up. It disappeared when I was about 12 or so not sure whatever happened to it.

    Like 1
  4. Rick

    I had also h-e-a-r-d that the limited market worked to thin the h-e-r-d. ;)

    Like 1
  5. jwaltb

    $40K definitely cools my ardor!

    Like 2
  6. Solosolo UK Solosolo UK Member

    My 1933 Calthorpe Ivory 500cc Twin Port would have been able to enter. When I bought it in 1978 the bike was in terrible shape and it took me until 2002 to restore it and I eventually sold it after retrieving it from a museum where it had been on display for 18 years. Very comfortable bike.

    Like 7
    • LMK

      And a very handsome machine it is too…Great results with your project…

      Like 1
    • chad

      My bet? most of that was parts sourcin? Congrats of the fine finish !

      Like 0
      • Solosolo UK Solosolo UK Member

        Actually the only parts that I had to source was the clutch assembly as it had been lost over the years. The original buyer had stripped the clutch and then got sent off to WW 2 army service and never came back. The parents kept it until about 1960 before my “old” friend bought it, did nothing with it, so I bought it from him complete but no clutch. I went up to Birmingham, UK, where the bike was built and visited only two classic bike spare parts dealers and was able to buy the whole shebang for about $30 in those days.

        Like 0
  7. Solosolo UK Solosolo UK Member

    As found in 1978

    Like 3
  8. TomP

    A few years ago I met an 80 year old lady at a biker bar in Colorado. She said she just finished up her yearly trip from Colorado to Alaska and back. She said she did that trip every year for 60 years.

    Like 2
  9. Jimbosidecar

    The Cannonball is on my bucket list but I don’t know if I’ll ever make it. The riders rolled into Las Vegas this afternoon. 57 riders rode in under their own power. Our local chapter of the AMCA were out in force to greet them and admire men (and one woman) and machines. 4 years ago we greeted them in Sturgis, SD and 2 years before than we greeted them in Kingman, AZ. To the riders-Quite an accomplishment!

    Like 3

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