Vintage Photos

20 Vintage Photos Of Classic Motorcycles And Sidecars (1910s-1950s)

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Two vintage black-and-white photos: On the left, a man in a leather jacket sits on a classic motorcycle. On the right, a woman sits on a motorcycle while two men and a child stand nearby, all in vintage clothing.
Via Anonymous88

Take a step back and hit the open road with this collection of 20 vintage snapshots of classic motorcycles and sidecars from the 1910s-1950s. It’s truly remarkable to note just how much both motorcycles and sidecars have evolved throughout the years. That being said, there’s something unmistakably old school cool about classic motorcycles and sidecars.

1. Seems to be a cheery-looking enough bunch

Three people in vintage military uniforms sit on a motorcycle, smiling for the camera. Another person on a motorcycle is visible in the background. The image is black and white, suggesting it is from the early to mid-20th century.

2. Now that’s a tough-looking crew of motorcyclists if I’ve ever seen one

Five men in vintage clothing sit on motorcycles, smiling at the camera. They are parked on a street with houses and trees in the background. The photo is black and white, evoking a mid-20th-century setting.
oldclassiccar

3. There’s something that doesn’t seem extremely safe about this helmet’s make

A black-and-white photo of a person wearing a helmet and jacket, sitting on a vintage motorcycle with the number 8, parked on grass near a white brick wall with two windows.
oldclassiccar

4. One of the classier outfits I’ve seen accompany an otherwise gritty looking motorcycle

A man in a trench coat leans against a classic Royal Enfield motorcycle on a country road, with rolling hills, fields, and stone walls in the background.
oldclassiccar

5. You’ve just got to love the motorcycle glasses

A man wearing goggles, a cap, and a leather coat sits on a vintage motorcycle in front of a brick building and a bush. The motorcycle’s license plate reads "RE 7486." The image is in black and white.
oldclassiccar

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6. We love a proper sidecar to accompany the throwback motorcycle

A black-and-white photo shows people in vintage clothing gathered near classic cars and a motorcycle with a sidecar. One man bends by the motorcycle, while others stand and chat in a tree-lined outdoor setting.
oldclassiccar

7. Of course this lad’s rocking the slicked back hair to go with his nice motorcycle

A man in a suit rides a vintage motorcycle on a residential street, smiling at the camera. A person on a bicycle follows behind. Brick houses and a picket fence line the background. The image is black and white.
oldclassiccar

8. Just a few motorcyclists taking a pause amidst what looks to be a nice journey

Three men in coats sit and stand by motorcycles parked along a country road, with trees and a fence in the background. The scene appears to be in black and white, suggesting a vintage or historical setting.
oldclassiccar

9. They don’t seem particularly thrilled to be stuck on top of that bike

A woman and a man sit together on a vintage motorcycle outdoors, looking toward the camera. Trees and foliage are visible in the background. The photo is black and white.
oldclassiccar

10. Every now and again the preppy lads like to take a crack at the whole motorcycles thing

Two men in suits smile and pose on a vintage motorcycle outside a brick building, one sitting on the seat and the other perched behind, both appearing cheerful and relaxed.
oldclassiccar

11. Now that’s an impressive little sidecar

A vintage black-and-white photo shows two men, one riding a motorcycle and the other seated in a sidecar with a young child. Another child stands behind the man on the motorcycle. All are dressed in early 20th-century attire.
oldclassiccar

12. This guy’s daughter has that impressive fearless energy about her

A black and white photo of an adult riding a motorcycle with a sidecar, where a small child is seated. Both are outdoors, surrounded by greenery. The image has a vintage feel.
oldclassiccar

13. Why so serious, fellas?

Two men in suits sit on an old-fashioned motorcycle parked on a cobblestone street, with a vintage bicycle and brick building with posters in the background.
oldclassiccar

14. Wonder if he was stopping in to see what “Costumes & Shoes” had for sale

A young man in a leather jacket sits on a vintage motorcycle, smiling at the camera. Behind him are old brick shops with signs reading "CAPSTAN" and "Costumes & Shoes." The photo is black and white.
oldclassiccar

15. Love the motorcycle glasses at play here

Two men sit on a vintage Ariel motorcycle in front of a brick building. The driver wears goggles and a jacket, while the passenger is in a suit. Both look toward the camera and appear to be in the mid-20th century.
oldclassiccar

16. Now that’s a nice fit to have with your motorcycle

A man wearing a suit and coat sits on a vintage Ariel motorcycle parked outdoors near a rural fence, with cows and trees in the background. The motorcycle has the license plate TL 216.
oldclassiccar

17. Family on a motorcycle with the exceptional sidecar in Morocco in 1936

A vintage black-and-white photo of four people and a dog riding a motorcycle with a woven sidecar on a dirt road. The sidecar holds three people and the dog, while one person drives the motorcycle.
vintageeveryday

18. Someone’s dad and his motorcycles in the 1950s

A man in a leather jacket sits on a vintage motorcycle in front of a wooden building. Another motorcycle is parked nearby, and the scene appears to be from the mid-20th century.
alman54

19. A girls’ weekend away with the motorcycle/sidecar tent combo

A woman in a striped top and shorts stands on a motorcycle seat, reaching up to adjust the window of a small, vintage tent attached to the back of a trailer, parked in an open, grassy field.
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20. A girl on a motorbike in the 1920s

A vintage sepia photo shows a woman sitting on a classic motorcycle with a license plate "CE5252," flanked by a young boy on the left and a man standing on the right, all in early 20th-century attire.
systepup

Explore more vintage content:

Ready for more rubber-meets-the-road nostalgia? Slide over to 15 Legendary Motorcycles That Made People Dream of the Open Road (1990s), and then you can check out 21 Vintage Photos of People’s Cars and Bikes in the Sixties.

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Meet the Writer


Matt Staff

Matt has spent over the last 8 years as both a writer and editor, working in Seattle and Brooklyn, where he is now based. He loves escaping the tirelessly fast pace of the “Mad Apple” that is NYC by taking walks and runs through parks where he’s able to catch up on the latest tea about society from the city’s ever chatty, always hungry, occasionally maniacal, pigeons. They always have a lot to say. When he’s not taking his urban nature strolls, or dutifully combing the deepest rabbit holes of the internet to find the content that’s worth sinking your mind’s teeth into, he’s likely holed up at a dark-lit dive bar with a new book and/or some friends, or just as easily he could be on the hunt for the next addition to his steadily growing plant family.

These days Matt’s caught up in trying to provide folks as many vivid glimpses into the days long since passed as he can, through fun and engaging collections of hand-picked vintage photos.



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