So Block Island

Block Island's Master Mechanic

There's no engine that adventurer Bobby Littlefield can't fix


Bobby Littlefield can fix anything. His nature is to start whatever stops, to build motors and businesses that move. He’s a master mechanic, entrepreneur, show car builder, captain and traveler – a true character epitomizing the island trait of self-sufficiency. Now that he’s got businesses on land and sea, it’s a big job to keep them all running.

It’s a particular person who approaches machines with curiosity and confidence. As a young man, it was common for Bobby to tear an engine apart, determine how it worked, then reassemble it, usually stronger and faster. He raced Crescent Beach sunsets in souped-up beach buggies, entertained the ladies in a cherry red Bronco and spun the tires off kit cars and classics, all while repairing island vehicles for 25 years at Littlefield Auto on Ocean Avenue. There’s a lot more to Bobby than car repair.

From his mainland shop, he builds the coolest cars, like ‘68 and ‘69 Camaros and a ‘36 five-window Dodge Coupe. He creates from the tires up, welding frames, grinding steel, melding smooth lines of beloved muscle cars with next-generation technologies and comforts. His masterful work has been featured in magazines, showcased on television and auctioned by Barrett-Jackson. His art reflects the builder: solid fundamentals, perpetual motion, high performance.

His summer home swings on an Old Harbor mooring, a skiff ride away from his parasail boat where for 29 years he’s flown countless visitors. Under bright skies, people glide above with spectacular views of the sea, steep cliffs and rolling hills as a crowded island sits silently. From his ten-meter Navy gun boat, Bobby offers wind farm tours; while on land, he rents summer necessities like umbrellas, paddleboards, boogie boards, bumper boats and chairs. He also donates banana boat rides and kayaks for Camp Mohegan, because that’s what islanders do.

“I’m headed to Cuba, then Turks and Caicos for the winter. I’ll go all the way back to Eleuthera, Cat Island and the Abacos,” Bob says casually. Nothing intimidates him – not a blown motor, not a gremlin in the wiring, not a pyramid of parts piled for reassembly with no directions. Long highways don’t intimidate him when he drives cross country for a perfect truck or boat or part to complete a custom creation. The ocean doesn’t either, as he sets sail for winter destinations where there’s fish to catch and machines to repair. It’s who he is.

Block Island is still home, so by summer, his parasail is ready. “It’s like a new year every year, like Groundhog Day. Everyone is having fun; it’s not like their cars are breaking down,” he says, which he could fix. It’s just more fun flying around with everything running smoothly.