It is not widely known that Rye, first settled in 1660, is the oldest community in Westchester County and one of the oldest in New York State. With the approach of our nation’s 250th anniversary on July 4, 2026, the coming months are a fine time to discover or revisit some of Rye’s many historic places.
A good way to start is by searching online for “Walk Rye History Signs,” which will take you to a guide on the website of the Rye Historical Society that says:
“Launched in 2010 to raise awareness of the town’s history, Walk Rye History is a self-guided tour that originally included 22 signs, incorporating photos and text, but more have been added. You can follow the tour online or in person.”
As shown on a map, the guide is divided mainly into sections: Downtown Rye, West Rye, Waterfront Parks, Milton Point, Boston Post Road Historic District, and Greenhaven.
The signs, conceived by Laura Brett and developed by Pam McGuire, were approved by the historical society board and the Rye City Council. Installed and maintained by the city, they contain fascinating photographs and information.
For an easy walking tour, start with the Downtown District where a sign will tell you that Rye City Hall was built in 1964, thanks to the generosity of a former mayor, John Motley Morehead. It replaced a movie theater (a favorite in my youth), which had burned down.
It will surprise many that the sign about the Church of the Resurrection states that its original site was located across Purchase Street in downtown Rye. After the current church was built farther south on the Boston Post Road, the “building now at 22 Purchase Street housed the much-loved Woolworth’s store from 1929 to 1990.”
Rye’s fire department dates from 1886. The sign says that the current firehouse opened in 1909 with a grand parade and a ball attended by 500 people.
The sign at the Post Office says that it is the fourth in Rye’s history, with the first located in the Square House. I had the honor of proposing to former Congresswoman Nita Lowey that the current building be named for Caroline O’Day, as a long-time member of Congress, who helped to have it constructed in 1936.
For another easy walking tour, head south to the Milton area. A sign explains that it was originally one of the Native American summer encampments before it became the first mainland village of settlors on land that they called Poningo Neck.
You will learn that local farmers brought their grain to be ground at the grist mills along Blind Brook in proximity to Milton Harbor’s tides. Ship captains lived nearby, and shipyards were built where the tides allowed building and repairs.
Still in the Milton area, you should visit the Bird Homestead and the Rye Meeting House. According to the sign: “The Bird Homestead provides a rare glimpse into 19th century life in a thriving maritime village.”
The “Walk Rye History” website will guide you to many other places. Shown below is a more recently added sign about “The Mill Pond,” which highlights the “Old Tide Mill,” also known as the “Kirby Mill.” This is worth visiting in every season.
