Nestled just to the south of White Plains’ vibrant downtown, the Highlands neighborhood stands as a welcoming tapestry of rich history, charming streets, and enduring community spirit. Whether you’re strolling along Gedney Way or pausing under a century-old oak in Gillie Park, the sense of heritage here is palpable. As a longtime resident, I’m proud to share the remarkable story of how Highlands became one of White Plains’ most treasured enclaves.
The Origins: A Name Rooted in the Land
The Highlands gets its evocative name from the elevated, rolling topography that distinguishes its landscape. In the late 1800s, as city growth began to spread from the bustling heart of White Plains, developers and early settlers were drawn to this area for its slightly higher ground—an appealing retreat from the low-lying, flood-prone zones closer to the Bronx River. It’s said that when the sun sets over the gentle rises of Ridgeway and Hartsdale Avenue, you understand immediately why the area is called the Highlands.
Early Days: Farms to First Homes
Much of Highlands was once part of sprawling Westchester farmland, dotted with orchards and stone walls. In the early 1900s, as White Plains became a commuter hub for New York City, a few visionary families saw potential in Highlands’ tranquil scenery and convenient location near the then-newly established White Plains Railroad Station.
Streets like Rosedale Avenue and Havilands Lane sprang up, lined with classic American Foursquares and Colonial Revivals. Early advertisements in local papers boasted of "fresh country air" and "quick streetcar access to Main Street." Residents enjoyed the best of both worlds—pastoral peace with city amenities just a trolley ride away.
Key Historical Milestones
- 1924: Establishment of Highlands School
The founding of Highlands Elementary School (now Highlands Middle School) on Gedney Way was a defining moment, shaping the neighborhood as a family-friendly community. Generations of local children have passed through its doors, fostering a deep-rooted sense of pride.
- 1930s: Gillie Park Named
One of Highlands’ gems, Gillie Park, was created on what had been open land at the foot of Mamaroneck Avenue. It quickly became a gathering spot for ball games, family picnics, and community events—traditions that thrive to this day.
- Post-World War II: Housing Boom
After the war, returning veterans and young families flocked to the Highlands. Cape Cods and split-levels replaced some older farmsteads, but the neighborhood retained its leafy, residential character. The sense of community stability grew even stronger.
Notable Landmarks and Beloved Buildings
- Highlands Middle School:
More than just an educational institution, this school is a landmark of the neighborhood—watchful on Gedney Way as generations come and go. Its well-kept brick facade hints at nearly a century of academic tradition.
- Gillie Park:
With its sprawling playing fields, playgrounds, and tennis courts, Gillie Park is the heart of Highlands outdoor life. It’s a hive of activity year-round, from Little League games in spring to snowmen in winter.
- Gedney Farms Library (now closed):
For decades, this small branch on Ridgeway served as a gathering place for readers and learners of all ages. Though it closed its doors, some neighbors still remember the story times and quiet afternoons spent among its stacks.
- St. Bernard’s Church:
Standing on Prospect Avenue since the early 1950s, this Catholic church remains an anchor for many Highlands families, hosting everything from holiday masses to charity drives.
How Highlands Has Evolved
The Highlands has always balanced old-world charm with progress. In the past few decades, younger families and new arrivals have restored historic homes and planted fresh roots. Streets like Hartsdale Avenue and Winston Drive showcase a blend of styles—prewar Tudors sit comfortably beside modern renovations.
The small shopping center at Mamaroneck and Ridgeway has seen generations of businesses—from corner grocers to local bakeries and coffee shops—helping neighbors stay connected in the daily rhythm of life. Community block parties and garden walks reflect the ongoing pride residents take in their homes and shared spaces.
Timeless Community Spirit
One thing that never changes in the Highlands is its spirit of unity. Whether through school fundraisers, volunteer clean-up days at Gillie Park, or neighbors helping shovel sidewalks after a snowstorm, there’s a deep sense of belonging here. Walking under the spring blooms on Miller Road, you’re likely to be greeted by name—a true sign of community in an ever-changing world.
In Closing: Heritage Lives On
Today’s Highlands is shaped by the footsteps of early farmers, builders, teachers, and families who saw the promise of this unique corner of White Plains. From the historic brickwork of Highlands School to the laughter echoing across Gillie Park, the neighborhood’s character endures through thoughtful preservation and, above all, the dedication of those who call it home.
Whether you’re a longtime resident or a newcomer admiring the sunset from Ridgeway, the Highlands is proof that heritage is not just about buildings and dates—but about the bonds that turn a place into a true community. If you find yourself wandering its tree-lined streets, take a moment to appreciate the stories all around you—they’re the heart of what makes the Highlands so special.