Sleepy Hollow High School - Class of 1959 Alumni

Join thousands of alumni from Sleepy Hollow High School and the Class of 1959. Reconnect with classmates, photos, yearbooks, upcoming reunions.

Varsity Football Schedule 2026-27

09/02 vs Byram Hills
09/09 vs Hendrick Hudson
09/17 vs Westlake
09/25 vs Hastings
10/01 vs Tappan Zee
10/09 vs Pearl River
10/15 vs Pelham Memorial
10/22 vs Briarcliff

Upcoming Class of 1959 Reunions

Browse past reunion events and photos for your class here.

Past Class of 1959 Reunions

Browse past reunion events and photos for your class here.

Sleepy Hollow '59 Apparel

Browse our apparel store for a wide range of Horsemen gear, from t-shirts and hoodies, to caps and accessories.

Class Yearbook

View past yearbooks

Recently joined '59 Classmates

Sally Sweet
Class of 1959

Connect with Class of 1959 Classmates

Ann Gazzola

Lauretta Johnson

Matthew Gaffney

Gordon Kuster

Mary Ann Bernald

Willard Grant

Nearby Sleepy Hollow Classmates

Class of 1957

2 classmates have joined

View Class of 1957 Alumni

Class of 1958

5 classmates have joined

View Class of 1958 Alumni

Class of 1960

8 classmates have joined

View Class of 1960 Alumni

Class of 1961

10 classmates have joined

View Class of 1961 Alumni