The center of Shelter Island, for all its charm and character, should have a name befitting all that it has to offer, and yet, it is called simply, “The Center”.
Route 114 runs through the Center, with municipal buildings including the Police Department, K through Grade 12 Public School, Public Library and the Courthouse.
There are also small stores that are in many ways the main-stays of Shelter Island commerce: the local grocery store, a greenhouse that also sells home-made pies, a down home diner, a bookstore, flower shop, video (or DVD) shop, a veterinarian, and a pottery shop, to name a few.
Historic Sylvester Manor, the first plantation on Shelter Island, which was a gift from King James to the Sylvester family, has been revitalized in recent years, becoming an organic farm. Its original windmill, the Nathanial Dominy Windmill still stands on Manwaring Road and was restored in 2021, overlooking the farm stand and farm fields. In recent years, the family sold its development rights of certain pasture lands to the Town of Shelter Island, which was an incredible gesture, which will keep these areas forever green. A book, “The Manor” was written by Mac Griswold recounting the history of the farm, founded as a New England slave plantation, providing valuable insight to the history of Shelter Island. The Quaker Cemetery, which is on Rte 114 and a part of the Manor, is a window to Shelter Island’s past when Quakers fled persecution and were given safe-haven within the plantation.
The Shelter Island Bucks, a regional baseball team, plays each summer in the field on School Street, next to the playground. The collegiate players offer a rousing time, with ice cream and hot dogs sold along the sidelines.
Each June, the Shelter Island 10K race is run, starting from the front of the Public School and ending on Fiske Field. This event attracts over 13,000 runners to the Island for a day, and features a pre race pasta dinner held at the Legion Hall adjacent to Fiske Field.
In August, the Shelter Island Crafts Fair is held on the school grounds, and many local artists have an opportunity to show their talents, from pottery, decoy duck painting, quilts, jewelry, photography, oil and water colors and much more.