Westchester Square, even to the present day, appears to be a small town hub, clustering around the triangle formed by Westchester, East Tremont and Lane Avenues. The “town” has recently celebrated its 350th anniversary, having been settled here, as Oostdorp (‘east village’) by the Dutch in 1654 and taken over by the British with the rest of New Amsterdam in 1664. It became a busy port along Westchester Creek, which hastened its development; by 1693 St. Peter’s Episcopal Church was founded. The parish is still in existence. During the Revolution, patriots dismantled a bridge over the creek, delaying British advancement (the present-day bridge carries East Tremont Avenue).
A separate monument in the square to area residents who served in World War I was dedicated with a speech by area educator Owen Dolan in 1925. After Dolan’s speech, by accounts a spirited, energetic one, he sat down and immediately dropped dead of a heart attack. Westchester Square Park was renamed for Dolan the following year, but today, his name is restricted to the square’s recreation center, a Spanish Colonial edifice containing a pool table and a kitchen among other amenities.