Pennacook avenue in Oak Bluffs is a street full of stories, the latest of which is a lovely coincidence. For most of its existence and for no known reason, at the Sea View avenue end of the street Penacook was spelled with one ‘n’, while at the other end on Circuit avenue, it was spelled Pennacook. On older maps, the diminutive Pennacook Park, separated by Niantic avenue, was named Park Park. Perhaps that’s unsurprising for those who live in the County of Dukes County, as written over the entrance to the Edgartown courthouse in the county seat.

Pennacook also served as the entrance to the Camp Ground’s gate in a fence separating the neighborhood’s pious from the potential sinners of the new (at the time) Oak Bluffs Land and Wharf Company real estate development. Today the area is known as the Cottage City historic district.

Once upon another time, in 1885 Edward Henry Fennessy (far left in the photograph) bought the house at 33 Pennacook (it is number 27 today) from his mother in law for his family that included his brother Frank (the taller man at far right in the picture). Frank was Edward (Ned) Fennessy 3rd’s great-grandfather.

Well known to many Islanders, Ned Fennessy was for 23 years the Martha’s Vineyard Regional High School tennis coach who led the boys team to its first state championship, followed by a second state title after a perfect 23-0 season. The high school tennis courts were named for Ned after his retirement in 2013.

What a delightful coincidence then, when after recently acquiring a property in Meadow View Farms, Amy Robertson Goldson found that her new next-door neighbor, Ned’s daughter, had built the house in 1961. Even more of a coincidence, conversation between the new neighbors turned up the fact that Amy’s dad, Irving (Buddy) Robertson, and mom Emily had bought the house at 33 Pennacook from the Fennessys, where Amy grew up during her summers in Oak Bluffs.

Skip Finley is the former Oak Bluffs town columnist and author of Historic Tales of Oak Bluffs, and Whaling Captains of Color — America’s First Meritocracy