Grand Avenue

How much do you know about the streets and roads of the Island?
How much do you know about the streets and roads of the Island?

Squire Frederick Chase — the namesake of Chase Avenue — created an ambitious development plan in 1836 for Shelter Island, mainly in the Heights.

But the dreams of Squire Chase, a prominent Island landowner of the time, were never realized, according to sources at the Shelter Island Historical Society (SIHS).

An early street plan from the SIHS shows that Grand Avenue was initially called Eagle Street, and that the streets perpendicular to Eagle Street honored the first five presidents.

In the early days of the Heights, builders imagined their settlement would become a great metropolis, with Grand Avenue as the central boulevard of shops and ornate homes. The homes on the stretch between West Neck Road and North Menantic Road made up an area “well known as ‘the City’ in the 1830s,” according to the SIHS.

Grand Avenue may not have become the imposing plaza of a shimmering city, but it has been and still is home to many beloved Island institutions. A short walk down the street will lead a visitor past the Shelter Island Heights Pharmacy, the Chequit Inn and Shelter Island Hardware. These three buildings in particular date back to as early as 1916, according to building records at the SIHS.

The thoroughfare inspires nostalgia in older residents. Many recall the “Pink House,” now painted red and home to Marie Eiffel’s clothing shop. The Shelter Island Reporter also once had a home on Grand Avenue. The “Gingerbread House,” one of the most distinguished landmarks of the Island and what every first-time visitor from the North Ferry remembers, originally faced the Prospect Hotel.

The distinctive structure has inspired many artists, photographers and appeared in modern fashion magazines.

SIHS records describe the Heights as “an area, which remains relatively unchanged since its beginnings as a summer resort 100 years ago.” This sense of permanence, as well as the Victorian-style architecture, creates a step back into the past, reaching across generations, for all who walk along streets such as Grand Avenue.