Photos by Polly Kreisman
Historic mansions, an observatory, Leona Helmsley’s gravesite, and more can be found along the retired aqueduct-turned-hiking trail.
Croton water was the answer. In the 1830s, New York City was decimated by fire and disease. Contaminated water fed the cholera outbreak of 1832 and killed over 3,000. The Great Fire of 1835 destroyed 600 buildings because there wasn’t enough water in wells or ponds to fight it.
What saved New York City was the Croton River in Westchester County, and one of the most ambitious engineering projects in local history: an aqueduct carrying water over 40 miles from the Old Croton Dam to Manhattan reservoirs, the largest at the site of the New York Public Library on Fifth Avenue.
By 1842, water flowed downhill to the city through a 7-foot-wide masonry tunnel, gently sloping 13 ½ inches every mile through the Old Croton Aqueduct, and crossing the High Bridge in The Bronx. With a supply of fresh water — 35 million gallons flowed through the aqueduct daily — the city thrived.
But the City grew so quickly, in 40 years it needed more water. In 1885, work began on a New Croton Aqueduct. The Old Croton Dam was submerged, and the New Croton Dam, the largest and tallest dam in the world at the time, came on line in 1906.

The Old Croton Aqueduct (OCA) stayed in service until 1955. “Now it gives people a chance to hike most of Westchester north to south without being on a road,” says Tom Tarnowsky, Board Member of the Friends of the Old Croton Aqueduct.
We are walking a wide, leafy stretch of the OCA Trail, looking west over the Hudson River. It runs on top of the aqueduct for 41 miles, still traceable in New York City. When it gets to Westchester County, it becomes a State Historic Park, passing through eight towns.
The Friends help the Parks Department preserve the 26.2-mile Westchester section of the trail, lead walks and tours, and publish a $5 full-color detailed trail map/guide of the Westchester or New York City sections.

Start in the city and hike all 41 miles, or do just the Westchester trail, and you’ll get a badge, however long it takes. “I got my badge,” says Friends Volunteer Michelle Pollack, but it took me 17 years.”
There are many points of interest both on and close to the trail. These are only a few, starting at the top, with the New Croton Dam. You can drive in at Croton Gorge Park below the Dam (a $10 charge,) but many people take Batten Road, park, and walk straight onto the dam. After a recent storm, it was sending a roaring 3,000 gallons of water a second down the 1,000-foot spillway.
Tarnowsky of the Friends, an impassioned encyclopedia of Croton Aqueduct history, says, “I come here at least once a week all year round. I like to see how the conditions change from day to day.” Croton resident Scott Hinman hiked nearby. “I’ve lived here for a year and a half and never knew this existed,” he says.

Walk across the dam — see if you can spot the misspelling of the word “height” on the historical plaque. The OCA Trail begins under a canopy of trees. Ambling down the northern most rural section, following the sounds of Croton Gorge, we pass the first of many tall cylindrical ventilators, stone towers about 20 feet high, built about a mile apart along the Aqueduct to circulate air and equalize pressure. Giant rock cuts show scars of gunpowder used to create the 66-foot-wide path, Tarnowsky explains, as there was no dynamite at the time.
A few miles south in downtown Ossining you’ll find the one accessible weir. Weirs were square chambers enabling workers direct access to the tunnel. On a guided tour with the Friends, you can descend the stairs and explore the original 1842 brick tunnel and machinery. Exit the weir onto a promenade on the Double Arch Bridge, where the aqueduct crosses Sing Sing Kill, an unusual landmark where one bridge crosses under another. There’s a nice walkway through downtown, but you will need the map when the trail dissolves onto city streets.
The most ornate of the old ventilator shafts now sits on the side of the road as you head south toward Sleepy Hollow. Just before Route 9, you will see a monument to the old Archville Bridge on the left side of the trail. It was demolished in 1924, abruptly severing the trail for decades. Now, there is a new steel walking bridge over the highway. Even on a Saturday in summer, parts of the trail in Sleepy Hollow offer solitude, at one point rising 80-feet over the Pocantico River, with easy access to Rockefeller State Park Preserve. You can slip through the back gate of Sleepy Hollow Cemetery and find some interesting graves; look for Washington Irving, Andrew Carnegie and Leona Helmsley, to name a few.
What saved New York City was the Croton River in Westchester County, and one of the most ambitious engineering projects in local history: an aqueduct carrying water over 40 miles to Manhattan…
Once you reach Tarrytown, a big draw is the Village itself; you can come off the path and into a lively scene of restaurants and stores. Then, on to where the trail narrows to a couple of inches wide across the front lawn of Lyndhurst, the Gothic revival mansion once owned by railroad tycoon Jay Gould. There are plans by the State to extend the path from Lyndhurst to a pedestrian bridge over Thruway I-87/I-287 but for now, follow the detours.

There are also many historic mansions near the trail in Irvington, including one of the country’s most unique houses, the pink, eight-sided Armour-Stiner Octagon House, and the stately Villa Lewaro, once a center for leaders of the Harlem Renaissance and home of Madam C.J. Walker, considered America’s first female entrepreneur when she invented hair care products for women of color.
At the side of the trail in Dobbs Ferry on a recent weekend, visitors wandered the exhibits in the 1857 Keepers House. In 2016, the Friends raised funds to restore the house, once home to a “Keeper” of the trail, an overseer, that is now the Visitor Center.
In Hastings-on-Hudson, the trail is part of the neighborhood. Crossing Broadway, you’ll see a yellow house at number 532, once a tavern, parts of which date from 1770. The nearby Draper Observatory is said to be where Henry Draper shot the first clear photos of the moon. And where the trail crosses Pinecrest Drive, walk up to see a trove of unusual historic homes. The whimsical, rambling castle-like structure at 131 Pinecrest was home to Met Opera Ballet Master Alexis Kosloff in the 1920s.

Another mile down the trail, you will be in Yonkers. The secret here, to many, is the Untermyer Conservancy, once known as America’s Most Spectacular Garden. The back entrance is on the trail. Walk up, between statues of a lion and a unicorn, for amazing views. Yonkers is the most urban expression of the trail. Volunteers from the Friends are working with residents to clean up some neglected areas that abut it. “Some homeowners identify with the trail,” says Friends Board Member Lesley Yu Walter, “some ignore it and some infringe upon it.”
Use the map to traverse downtown Yonkers into Tibbetts Brook Park. Soon, you will have come 26.2 miles to the New York City border, where a stone honors the Aqueduct that saved it, and the trail it left behind.