All aboard for a rollicking ride through Rye's past! Join the Rye Historical Society on September 20, 2026, for a breezy, air-conditioned trolley tour, "From the Gilded Age to the Roaring Twenties"

Picture this: You're cruising in a vintage trolley, past the swanky summer digs of New York’s elite and hearing tales of how the railroad turned sleepy Rye into their playground. We'll get a peek at one of their exclusive clubs and imagine the high times!

Then, hold on to your hats as we trace the old trolley tracks down to the shore, where Rye Beach exploded with fun! Think bustling hotels, summer cottages, massive clam bakes, thrilling amusement parks, and the birth of the iconic Rye Town Park and Playland Park. Get ready for juicy stories and a vibrant look at our historic waterfront!

Recommended for children 10+

Commencing at Nursery Field parking lot (parking available), 421 Milton Rd, Rye, NY, concluding back at the same location.

Please note that Trolley boarding will begin 15 minutes prior to departure. We cannot guarantee large parties will sit together unless they plan to arrive early to secure seats. The Trolley will depart promptly at the scheduled tour time.

Brought to you by the Rye Historical Society with the generous support of our
Tour Leader Sponsor:

Real Estate Salesperson

Rye Brokerage

14 Elm Place Rye, NY 10580

View my site

Mobile Phone: (914) 420-5461

About The Rye Historical Society

The Rye Historical Society was founded in 1964 by a group of concerned citizens who banded together to preserve, restore and protect the Square House, an 18th century inn located on the Village Green in Rye.

After faithfully restoring the Square House, the Society has maintained it as a house museum. In 1980, Rye History received accreditation from the American Alliance of Museums. The Society acquired the Timothy Knapp House, Westchester County’s oldest surviving house, in 1992, restoring and opening it to the public in 2001 as an archival and research center.

The Society continues to serve the community through school visits and programs, vacation and summer programs, lectures, exhibits, walking tours and numerous family and community events throughout the year.

Photo credit: Rye Trolley and the Square House from the RHS Archives (1906)

September 20, 2026: Rye Historical Society Gilded Age Trolley Tour

Presented with the generous support of realtor Susan (Sue) O'Brien