Leonard’s Motor Service, known in its earliest days as “Lake Avenue Garage,” was located in downtown Oak Bluffs where Jim’s Package Store stands today. The dapper gentleman in hat, spectacles, and necktie on the right is owner Alpha Leonard, a 1904 Brown University graduate who served as school principal in Bath, N.H.; Camden, Maine; and Attleboro before moving to the Island to become Oak Bluffs High School principal from 1915 to 1919, and then Tisbury High principal about 1920.
An avid sportsman and athletic coach, Leonard was a talented skeet shooter, trapshooter, and archer, and as treasurer of the Rod and Gun Club, he enjoyed teaching the mastery of both gun and bow. He was also a licensed pilot. In 1921 he left education to buy this garage and service station (initially with a partner, whom he soon bought out), and ran it for 45 years. It was renamed “Leonard’s Motor Service and Sport Shoppe,” and is still fondly remembered for its penny candy counter. During the 1950s Leonard’s was a Hudson dealership as well, selling Hornets, Wasps, and Jets.
Alpha’s oldest son Freeman worked there for decades as a mechanic, and by the late ’40s his younger son Howard became his business partner. It was sold in 1966, and became Ben David’s Garage.
Chris Baer teaches photography and graphic design at Martha’s Vineyard Regional High School. He’s been collecting vintage photographs for many years.