From the Nursery Field parking lot, the trolleys rolled onto Milton Road and into history.
More than 65 residents, from elementary school students to senior citizens, showed up recently for Rye Historical Society’s “From the Gilded Age to the Roaring Twenties” trolley tour and picnic.
“The tour was a reminder that there are hundreds of years’ worth of stories, controversies, and patterns that bring us to the current moment,” said Linsey Furnary, who joined the tour. “Visiting the sites made the experience come alive and feel even more relevant to contemporary Rye.”
The tours are the brainchild of Joie Cooney, a trustee of the Historical Society. They filled two trolleys, with Cooney narrating one and trustee Melinda Mehfar the other, and included stops at Wainwright House, American Yacht Club, and Rye Town Park.
As the rented trolleys rolled over modern roads, the tour guides explained that the city once had trolley lines connecting Rye to surrounding towns and carrying visitors from the train station to the beach. The tour explored the history of waterfront recreation on Milton Point, from the summer estates to the bustling beaches.
The first event of its kind for the Historical Society, the event raised more than $7,000.
Cooney, who had previously organized walking tours in Rye, won praise from Furnary.
“Joie overlaid fascinating tales from the earliest families to the Civil War and beyond. It was gripping,” she said. “There is so much more to Rye than meets the eye!”
Passengers boarded the refurbished New Orleans-style trolleys, maps and commemorative tickets in hand. Along the way, they learned that the Wainwrights had originally owned a few large properties on Milton Point, including what is now the Coveleigh Club. The Wainwrights were influential in Rye and on a national scale. General Jonathan Mayhew Wainwright IV served in both World War I and World War II, when he was captured and made a prisoner of war. The Wainwright family includes members of Congress, veterans, artists, musicians, and community leaders. Today the Wainwright House operates as a nonprofit offering a range of programs.
At American Yacht Club, Libby Alexander, the first woman to serve as Commodore of the club, greeted the crowd and gave an overview of the club’s history from its early days of steamships to the development of recreational sailing. She described the fire that destroyed the original building, and highlighted features of the new building from a mural behind the bar to the view of the rock formations known as Scotch Caps.
“I was happy to host the Rye Historical Society at our beautiful club and share some of our incredibly rich history dating back 142 years to our founding in 1883,” Alexander said after the tour.
Under the pavilions at Rye Town Park, visitors learned the history of the beachfront bungalows, hotels, and restaurants that preceded the park’s development. The tour then highlighted some of the bungalows as it traveled along Beck Avenue and other surrounding streets. Many of the original structures were relocated when the park was built in 1908. The now-winterized homes are about 120 years old, a reminder of a bygone era.
Traveling along Midland Avenue, it was easy to picture the trolleys from long ago taking the same route. Tour takers learned that the wide street was designed to accommodate the original trolley line with an extra lane in the middle. Originally known as Meadow Avenue, this thoroughfare, along with Milton Road and Forest Avenue, connected Milton Point with downtown Rye.
Rising sixth grader Owen Beardsley was surprised by the whole experience. “I learned so many facts about places we usually drive by, not knowing the interesting stories behind them,” he said.
The tour concluded with a picnic at the Knapp House, the oldest house in Westchester County. Dating back to the late 1600s when Milton was known as Mill Town, the house was owned by the Halsteads and then the Fords, both of whom were influential in shaping Rye history.
