This vintage wooden skateboard is a rare find for any collector or enthusiast. Featuring the iconic Stars and Stripes design, this board is a tribute to the classic 1960s Indy 500 races. Made by Sport Fun and bearing the model name Stars, this skateboard is perfect for anyone looking to add a unique piece to their collection. Whether you’re a skater or just a fan of vintage sports memorabilia, this board is sure to impress.
One of the earliest boards. A piece of history. Made by Fleetwing I think they missed an opportunity… It would have been way cooler to be “Feetwing” or… Metal wheels with dope matching yellowing hubcaps. 18.5″ L x 4.5″ W. Note the small chips along the edge of the board and the black sneaker scuff marks. ? Early Skateboarding History (1950s-early 1960s): The Wood & Metal Era. Origins : Skateboarding began in the 1950s in California, as a land-based version of surfing-often called sidewalk surfing. Surfers improvised by attaching roller skate wheels to wooden planks. Decks : Made from simple wood planks, often straight and flat with no concave or kicktail. Sometimes cut from surplus wood or repurposed from other uses. Wheels : The earliest skateboards used steel or metal wheels -typically from roller skates. These wheels offered poor grip and a rough ride, especially on uneven pavement. Ride Quality : Steel wheels made skateboards dangerous and unpredictable -they’d skid easily, and small rocks or cracks could stop them instantly. Despite this, kids rode them in streets, driveways, and empty pools. DIY Culture : Most early boards were homemade, especially before commercial production began. Creative modifications and experimentation were common. Companies like Roller Derby, Val Surf, and Makaha started producing skateboards for sale in stores. These boards were still wood with metal wheels, although clay composite wheels soon replaced metal around 1963, improving safety and performance. With the clay wheel improvement and surf-style marketing, skateboarding boomed in popularity. Major brands and magazines emerged, and competitions began.
One of the very first longboards! A piece of history! Of the era whereby skateboarding was marketed as a means to learn how to surf “sidewalk surfboard”. 35″ L x 5.75″W. Has a cool logo of a guy on surfboard. It’s in fair-good condition: it has just enough wear to give it street cred, but is still legible. History of early wooden longboards with metal wheels, often known as “sidewalk surfboards” in the late 1950s and early 1960s. The Origins of Skateboarding: The “Sidewalk Surfboard” Era (1950s-early 1960s). ???? Roots in Surf Culture. Skateboarding began in California in the 1950s, invented by surfers looking for a way to “surf” when the ocean was flat. The earliest boards were homemade, using wooden planks and attaching metal roller skate wheels to the bottom. These makeshift boards were nicknamed “sidewalk surfboards” to emphasize the connection to surfing. Decks : Flat, solid wood-usually rectangular or slightly rounded, sometimes shaped like small surfboards. Wheels : Steel or cast metal wheels taken from roller skates. These offered little to no grip, a very rough ride, and could easily lock up on small debris. Trucks : Often scavenged or rudimentary, lacking the responsiveness of modern skate hardware. Early skateboarding gained national attention when Life Magazine published photos of sidewalk surfing in the early 1960s. Local competitions and skate demonstrations boosted visibility. Safety issues due to steel wheels and lack of control led to numerous accidents. By 1965, the first skateboarding craze had started to fade, partly because of injuries and negative press. In 1963-64, clay composite wheels started replacing steel. In 1973, urethane wheels were introduced by Frank Nasworthy (Cadillac Wheels), completely transforming the sport.
The product is a vintage Sears & Roebuck skateboard from 1965, featuring a hot dog design with red clay wheels. This sidewalk surfboard is 28.75 inches long and embodies the theme of The 60s, making it a unique and nostalgic item for those interested in vintage skateboarding and longboarding. Perfect for collectors or enthusiasts looking to add a piece of skateboarding history to their collection.
By the Chicago Skate Co. I love that you can feel the movement and speed in the logo all in a mid-century font! Unique, oblong shape (24″ L x 6.75″ W x 3 W). Unlike the skateboards of the time that used skateboarding as a means to learn how to surf “Street Surfing”, this one went the other way and suggests that if you use it, you can learn now to ski… It’s a “Ski-Board”. Very rare – the only example I’ve ever seen. Some faint black scuffs on the tail end of the deck.
A piece of Americana! This hails from the 60s when skateboarding was being marketed as an easy way to learn how to surf “Sidewalk Surfing”! This has been professionally re-finished in the last couple of years; new lacquer and new vinyl decals.