From the 1890s into the early 20th century, trolley cars carried passengers throughout Rye, along Stuyvesant, Dearborn, Forest, and Rye Beach avenues.
Now the Rye Historical Society is planning to give people the chance to relive that history with a trolley tour scheduled for July 20.
The event, to showcase Rye’s history from the Gilded Age to the Roaring ’20s, will highlight not only historic sites in Rye, but also the iconic trolley ride itself, which shaped this seaside town.
The tour will cover some of the areas where the original trolley tracks ran. The trolley lines helped create the recreational beach areas from Oakland Beach to Playland Beach. And while the trolley cars were retired long ago, their existence had a lasting impact on Rye landmarks.
The trolley tour is the brainchild of Rye Historical Society board member Joie Cooney, who has led walking tours focused on Rye history in recent years. Cooney helped create walking tours of Milton Point and Rye’s Dublin neighborhood, and also expanded the programming for local Native American history. The trolley tour is the latest, and perhaps most ambitious, of Cooney’s projects for the Rye Historical Society.
“Since Rye Historical Society does not do a gala every year, I was looking for something special we could do that would be more significant than a walking tour and might be able to include more people,” Cooney said. She added that she has been interested in the historic trolleys since seeing postcard images of them.
The society hopes to sell 65 tickets for two trolleys, each covering the same paths but in opposite directions. The ride is to begin at Nursery Field at 10:30 a.m. and end with a picnic on the grounds of the historic Knapp House next door.
The trolleys, which will be rented from a Yonkers company that refurbishes trolleys from New Orleans, will not be exact replicas of the ones that traversed Rye. But the historical society expects that with the help of knowledgeable tour guides and stops at historic locations, riders will be transported to a different era.
To honor the Gilded Age, the trolley will tour the summer estates along Stuyvesant Avenue, including the Wainwright House and American Yacht Club. The tour then will travel along Dearborn, Forest, and Rye Beach avenues to explore the early 20th Century history of Rye Town Park and Playland, including the beach bungalows, hotels, and other amusements that predate the current landmarks. It will then continue toward downtown Rye before circling back. The original trolleys ran in front of the Square House, a scene captured in one of the historic postcards that will be shared on the tour.
Jackie Jenkins, president of the Rye Historical Society Board of Trustees, said the trolley tour aligns with the group’s mission of offering hands-on learning and new ways to experience history.
“A big part of our mission is to bring people interested in our local history together to learn about that history,” she said. “Whether it’s why a particular neighborhood sprung up where it did or how we went from being an agrarian community to a commuter town, finding out the answers to questions like these helps one form a connection to our past and beyond. Just knowing a fun fact about a landmark we see every day helps us understand why the people who came before us and their stories matter.”
She added that the trolley tour will enable participants to see locations and buildings that are too spread out to cover in walking tour.
Cooney said the trolley tour, if successful, could become a regular offering. The Historical Society suspects there were previous trolley tours in town, but they have been unable to pinpoint a specific date.
Cooney is adding her own spin to the tour, creating a playlist of trolley-themed and other popular music from the era.
Judy Garland would be smiling.
Tickets are $60 per person and are available at ryehistory.org. A boxed lunch from Milton Point Provisions is an additional $20 per person. There are ticket bundles and sponsorships available. Any additional $50 donation includes commemorative postcards.
