All Aboard! A Trolley Tour of Historic Scarsdale

Climb aboard for a journey through Scarsdale’s past as we celebrate the Village’s 325th anniversary (and America’s 250th)!

Scarsdale Trolley Tour 
📆 November 1, 2026
Departures at 10:00 AM, 12:30 PM & 3:00 PM
Members: $30 | Non-members: $45

EVENT IS NOW SOLD OUT.
Spots may open up. Join the waitlist and we’ll let you know if tickets become available.

This family-friendly 90-minute guided trolley tour will explore the people, places, and stories that shaped early Scarsdale—from colonial farms and the Revolutionary era through the age of country estates, when horses still traveled Scarsdale’s roads.

Along the way, we’ll uncover remnants of an earlier Scarsdale that are still all around us—historic homes, former estates, and places where Revolutionary War events unfolded, all hiding in plain sight if you know where to look.

Tickets are very limited. Scarsdale Historical Society members receive a special discounted price.

Not a member? Now is a great time to join!

***
FAQ

Where does the trolley tour begin?
The starting location and arrival instructions will be emailed to ticket holders before the tour.

How long is the tour?
The tour is approximately 90 minutes.

Is there a bathroom on the trolley?
No. There are no restroom facilities on the trolley, so please plan accordingly before departure.

Does the tour take place rain or shine?
Yes! The trolley tour will take place rain or shine.

Is the tour family-friendly?
Yes. The tour is family-friendly and open to history lovers of all ages.

How early should I arrive?
Please plan to arrive at least 15 minutes before your scheduled departure. The trolley must leave on time, and we cannot guarantee that late arrivals will be accommodated.

Is the trolley accessible?
Please contact us in advance with any accessibility questions or needs so we can determine what accommodations are available.

Can I bring food or drinks on the trolley?
While not prohibited, food and drink should be limited.

Do I need to bring a printed ticket?
No printed ticket is necessary. Please have your Eventbrite confirmation available on your phone at check-in.

Can I change my tour time after purchasing a ticket?
All sales are final, and tour times cannot be changed after purchase.

Are tickets refundable?
All sales are final.

Can I buy a ticket on the day of the tour?
No, ticket sales will close before the event. Each trolley has limited seating, and tours may sell out.

Will passengers be getting on/off the trolley during the tour? 
We will be getting off the trolley once, weather and time permitting, for 5 minutes.

Can passengers board at a later stop or depart the tour early?
Passengers must board at the beginning of the tour. They can always get off the trolley to leave for an emergency, but they will need their own transportation back to the starting point.

Whom can I contact with questions?
Email us any time at info@scarsdalehistoricalsociety.org.

Join Us at Mamaroneck 250

Commemorate the 250th anniversary of the American Revolution with live music, storytelling, historical reenactments, hands-on exhibits, and activities for the whole family at a Living History Family Day:

📆 Sunday, October 18, 2026
Harbor Island Park · Mamaroneck, NY

** Special Reenactment at 1:30 PM **
Full event runs 1:00–5:00 PM

We’re revisiting the British army’s advance through our area in October 1776 - as General Howe and British Loyalists Phebe and Edmund Ward recount their experiences during these pivotal days and beyond, including stories of confiscation and divided loyalties.

From the moment British forces landed at Pell’s Point, they sought strategic locations and homes to serve as headquarters for General William Howe as his army advanced toward White Plains. Howe established headquarters throughout the area, including in Pelham, New Rochelle, Larchmont, Eastchester and Scarsdale. Hear General Howe and British Loyalists Phebe and Edmund Ward recount their experiences during these pivotal days and beyond, including stories of confiscation and divided loyalties.

In October 1776, Howe commandeered the Eastchester home of Patriot Stephen Ward before establishing headquarters at Scarsdale’s Griffen-Fish House on Mamaroneck Road. Situated on high ground overlooking the surrounding countryside, the Griffen-Fish House offered a strategic vantage point over today’s Post Road as British forces pursued Washington’s army toward White Plains.

At this event, hear their stories and learn more about local history at The Friends of the Ward House, The Eastchester Historical Society, and The Scarsdale Historical Society

---

Toast 250! at Wayside Cottage - Sunday, June 14th

Wayside Cottage is the place to be on Sunday, June 14th, from 2 - 6 PM! 

Hosted by RW250 and the Junior League of Central Westchester, this lively Revolutionary-era tavern experience celebrates the Semiquincentennial (1776-2026) and the 325th anniversary of Scarsdale with music and merriment for all ages.

At Scarsdale Village’s oldest landmark, we’ll celebrate where the Varian family faced ever-present danger from Loyalist and British attacks during the Revolutionary War years.

FEATURING

Visits from: Martha Washington ★ British General Howe ★ Patriot Col. John Glover ★ …and More

Music by The Liberty Three

Games Hosted by Philipse Manor Hall

Quill Pen Writing

Weaving Demonstrations

Musket Drills with the 5th New York Regiment

Wayside Cottage Tours

Recognition of Witness Stones Project Honoring Those Once Enslaved

American Revolution Trivia—The Westchester Edition! (4:00 PM)

Tavern Fare and Libations for Purchase at the Captain Lawrence Food Truck

Colonial Sweets, Including Flag Day Treats for Kids

---

FREE ADMISSION

📆 Date: Sunday, June 14
2:00 - 6:00 PM
Wayside Cottage at 1039 Post Road, Scarsdale, NY

All Ages Welcome

Watch Now: Scarsdale's Revolutionary Transition

Scarsdale’s Revolutionary Transition: From Colonial Manor to American Town

Scarsdale Village Historian and Scarsdale Historical Society Vice President, Jordan Copeland examines Scarsdale’s transformation from a colonial manor to an American town in the aftermath of the Revolution. It explains what it meant to live under the manor system, how Scarsdale was governed before independence, and what changed when that structure gave way to town government. Drawing on surviving records from the 1700s, the talk explores what we know about daily life in Scarsdale, including what mattered most to its residents, how authority was exercised, and how early residents contributed to the creation of a community.

This program was presented live at the Scarsdale Library on March 16, 2026.

School History Documentary Screening Recap – The Film Is Now Online

The Scarsdale community really knows how to “show up.” Around 200 alumni, neighbors and friends came together for a rare opportunity to celebrate our public school district on Wednesday night at the high school auditorium. As conveyed in our new film From the First Schoolhouse: A Scarsdale Story, this community-minded spirit is what has helped the Scarsdale Schools thrive. 

Left to right: William Klayer ‘73, Tony Arenella, Ruth Friendly, Scarsdale Historical Society President Randy Guggenheimer, filmmaker Lesley Topping and trustees Lori Rothman, Deidre Michael, Leslie Chang.

From a beloved centenarian educator, to a founder of the Scarsdale Alternative School, to an original Alternative School alum, we had true Scarsdale Schools legends in the high school auditorium. They are featured participants in the documentary, and here’s more background on them:

Ruth Friendly

Ruth taught at Greenacres, Heathcote, and Edgewood from the 1960s through the early 1980s. After teaching, she joined her husband Fred, the former president of CBS News and the Edward R. Murrow Professor Emeritus at Columbia University, to produce programming for the Media and Society Seminars, later known as the Fred Friendly Seminars. The programs aired nationally on PBS and explored major issues of our time. In the 2000s Ruth served for eight years on the New York State Commission of Nomination for the Court of Appeals.

Tony Arenella and William Klayer

Tony Arenella was one of the founders of the Scarsdale Alternative School (A-School), which was planned in 1970. Tony taught English, and then became the director of the A-School in 1981 until he retired in 2003. Beginning with only sixty-two students, three full-time teachers, and several part-time teachers, the early team developed the groundbreaking philosophies and structures that still shape the A-School today.

William Klayer was one of the first students to graduate from the A-School in 1973, and went on to build a distinguished career in television and film as a director and photographer. His extensive credits include 30 Rock, Suits, Law & Order, and the award-winning short film Under a Stone.

We are so grateful to the filmmaker Lesley Topping for creating this film. Through her documentaries, she skillfully preserves Scarsdale’s most important stories—and they’re all available here.

Lesley Topping

Lesley, a Scarsdale Schools alum, is the editor and director of the film. Her credits also include many short videos, feature films and television documentaries for CBS, A&E and the Cousteau Society.

Thank you to Scarsdale Public Library for the partnership and for co-sponsoring the event. Don’t miss their new exhibit on the Scarsdale Public Schools, created by the library’s Local History Librarian Dan Glauber. It’s on display in the Local History Center of the library, or online here.

We also thank Scarsdale Public Schools Superintendent Drew Patrick for his support throughout the production of this film. His opening remarks added a moment of extra distinction to the event.

Scarsdale Public Schools Superintendent Drew Patrick introduced the film.

The audience was very engaged during the Q&A Session, especially all of the alumni that shared stories from their school days.

At the panel discussion, left to right: Dan, Leslie, Lesley, and William. Tony and Ruth answered questions from their seats in the audience. 

Scarsdale Historical Society trustees greeting attendees, from left to right: Lori, May Cowan, Lesley Shearer, and Leslie

The event drew a crowd of all ages, and alumni enjoyed seeing the newly renovated auditorium.

“From the First Schoolhouse: A Scarsdale Story”