The North Eastham property upon which the Hole in One Donut Shop and the Fairway Restaurant & Pizzeria now sit was once a stretch of unbroken turnip fields. 

This all changed in 1938, when the construction of a new highway sliced right through these turnip fields, prompting its owners, Emerson Wentworth and his wife, to build a slew of cabins alongside the newly-paved roadway. “Wentworth Acres” was later owned by the Benz family, followed by Joseph and Marie McWilliams, and eventually by Frank and Dot Riordan, who transformed it into its current commercial success: the Hole in One Donut Shop and the Fairway Restaurant & Pizzeria.

Since 1989, the Bazzano family has owned and operated the Hole in One Donut Shop and the Fairway Restaurant & Pizzeria, adding a third location, the Hole Donut Shop & Deli in Orleans, three years later.