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On one of those “not a cloud in the sky” summer days, we headed north out of New York City for a mountain bike ride on the northern section of the Old Croton Aqueduct State Historic Park Aqueduct Trail. Created in 1968, this Hudson River Valley National Heritage Area Linear Park runs about 26 miles along the path of the first water supply system to carry water to New York City. It ran from the Croton River (a tributary of the Hudson River), near Croton-Harmon in Westchester County to the Yonkers - New York City line at Van Cortlandt Park. For over 165 years, the Croton Aqueduct Trailway has linked communities and historic sites along the lower Hudson River. It runs atop the underground masonry water tunnel that brought clean water from the Croton Reservoir to New York City Reservoirs from 1842 to 1955.
The 5 mile, one way trail segment from Old Croton Aqueduct State Historic Park (Croton Gorge Park) to the historic Hudson River town of Ossining, NY is one of the most scenic and fascinating bike rides or hikes that you can do along the Old Aqueduct Trailway.
The bike route takes you on a journey through dense woodlands and open spaces, alongside streams and gorges, past backyards and historic sites. The theme is "Americana" as you bike through the “Main Streets” of historic Hudson River towns. Along the way you will gain fascinating insights of life, times and views along the Croton and Hudson Rivers.
The trail surface is varied, ranging from wide and smooth hard-packed dirt trails to doubletrack and narrow dirt singletrack through grass. Except for a few detours that include a short ride along a chainlink fence delineating industrial property., steep grades or on-road sections, the trailway is relatively flat making this a bicycle ride that everybody will enjoy. A mountain bike or hybrid bicycle is recommended.
Croton Aqueduct Trail Connections
While this article focuses on the Croton Aqueduct Trail segment from New Croton Dam to Ossining, other suggested trail segments are: Sleepy Hollow to Dobbs Ferry; Dobbs Ferry to Yonkers; Greystone to Hastings, Dobbs Ferry or Irvington. Each provides a unique bicycling experience with many fascinating points of interest along the way including The High Bridge (originally the Aqueduct Bridge) which is the oldest bridge in New York City; Hudson River Lighthouses; The Old Croton Aqueduct Trail Keepers House in Dobbs Ferry; Sleepy Hollow (National Historic Register Old Dutch Church of the Manor of Phillipsburgh and Cemetary) that tells tales of the "Legend of Sleepy Hollow and the Headless Horseman"; Revolutionary War sites; Up The River to Sing Sing and more.
North-South County Trailway
Paved, multi-use trail spans 36.2 miles through Westchester County. The North section runs 22.1 miles from Eastview in the Town of Greenburgh north to Putnam County. The southern portion runs for 14.1 miles all the way to the New York City border. Can be accessed from Towns along Old Croton Aqueduct Trail such as Sleepy Hollow, Tarrytown, Scarsboro and even from the Graham Hills Park Mountain Bike Trail network.
Briarcliff Peekskill Trailway
12-mile Linear Park (No Bicycles) built on lands that were originally intended to become a parkway. It connects Croton Gorge Park to Blue Mountain Reservation in Peekskill and Route 9A. Trail ofshoots lead to the Kitchawan Preserve, John E. Hand Memorial Park, Teatown Lake Reservation and Cortland Manor.
We made the 97-acre Croton Gorge State Historic Park our base of operations. Not only does it provide direct trail access, It s situated at the base of the 301-foot high, New Croton Dam that arcs across the Croton River. Held in restraint by hand-hewn masonry walls, the river powers over the spillway in a frothing waterfall. Picnic tables strategically placed around a field punctuated by magnificent tall shade trees, offer ringside seats with unobstructed views of the arcing walls and the cascading water. It's as scenic a spot as you can get at a New York City Reservoir and the perfect spot to relax before or after your bike ride and enjoy a picnic lunch.
You can easily access the Croton Aqueduct Trail (OCA) from the far end of the parking lot next to the restrooms at Croton Gorge Park. After a short steep climb along a gravel switchback, you intersect the OCA Trail. A left at this intersection will bring you to Croton Dam Road, which runs along the top of the dam affording spectacular views of the dam, river gorge and spillway from a different perspective. We did this at the end of our mountain bike ride, when we could spend more time to gawk in wonder. Being the daughter of a U.S. naval, marine structural engineer, who was a whiz at building origami ships out of one peice of paper, has given me a keen sense of appreciation of engineering marvels. Road use is limited to pedestrians, bicycles and emergency vehicles only.
Turn right and start mountain biking south. This wide dirt section of the trail travels uninterrupted for almost a mile through dense forest along a scenic route carved into the hillside high above the Croton River ravine. You will immediately notice what appears to be a stone tower rising up out of the ground. This is the first in a series of cylindrical stone ventilators.These are spaced out along the trail at about one mile intervals. The aqueduct ventilators allowed fresh air to circulate over the water in the tunnels below.
At about 2 miles (between the 2nd and 3rd Ventilators) you'll bike over a bridge that travels over a deep gorge on the right. This is the Croton Gorge Unique Area (look for the sign), which is managed by the New York State DEC. Many trails (hiking) traverse this scenic 22 acre wooded, undeveloped area situated at the crest of the Croton River ravine. There is a small parking area for 3 or 4 cars. You can hear the stream tumbling over the rocks in the gorge far below. At around 3 miles you'll arrive at the first detour along the trailway. After a short steep ascent there is a on-road section through a residential area.
OPTION: For an easier round trip of under 6 miles, especially if biking or hiking with kids, you can turn around before the detour and return to Croton Gorge Park.
To continue your mountain bike ride, turn right and look for a green wooden post with the letters OCA. A narrow grassy trail with dips and roots takes you up and then down past the General Electric Leadership Development Center along a chain-link fence that borders the property. You'll emerge onto Shady Farm Road.
Make a right turn here and then go left under the bridge to bypass Route 9A. Follow Old Albany Post Road up the hill, then turn left up steep Ogden Road. At the top, the trail continues to the right, opposite another green OCA post. This detour is about .75 miles. You'll come to another ventilation shaft at 3.75 miles, where you will have to push your bike up a short, but steep rocky hill to Piping Rock Road.
OPTION: To avoid this steep incline you can continue on Albany Post Road which turns into N. Highland Ave. Continue biking and you will rejoin the trail where it crosses Route 9. This detour takes you along busy Route 9 (N. Highland Ave.). Use caution.
After either biking or hike-a-biking over the hill, cross Piping Rock Road and continue to Route 9 at 4.1 miles. Cross Route 9 and continue straight on the trail. You are now entering the town of Ossining. Here the route can get a little confusing. At about 4.75 miles you'll reach a square stone building that provided access to the aqueduct below for the maintenance crew. At around 5 miles the trail enters the Old Croton Aqueduct Promenade, a linear park that is the Downtown Ossining portion of the aqueduct that runs directly above the water tunnel. Follow the paved path up the hill and then down the steps on the other side. Cross another road to the Ossining Weir Chamber. This large, square stone building provides access to the Old Aqueduct underground.
Cross over the Sing Sing Kill Gorge on the top of the Aqueduct. On the other side, a path to the left leads to the Visitor Center in the Joseph Caputo Community Center building, and a path to the right leads down to a viewing platform where oyu can get views through the trees of the Double Arched Bridge you just crossed. The now brick-lined trail leads onto Main Street, the endpoint of our featured bike ride. You'll find cobblestoned streets lined with many historic buildings. Visit one of the shops for refreshments and take the time to enjoy your snack and Ossining ambience on one of the benches you'll find along the street.
No time or inclination to retrace your route back to the start? Take the Metro North train from the Ossining Station to Croton-Harmon station. From there, it's a short bike ride to Croton Gorge Park and less than 50 minutes to New York City.
See Transport Your Bike for travelling with bicycle policies.
Trail Highlights and Nearby Points of Interest
Sing Sing Kill Greenway & Double Arched Bridge
0.5 mile (round trip) paved ADA compliant walkway along the scenic Sing Sing Kill’s rocky gorge. The walkway was originally a path to allow work on a sanitary sewer project. Today it has been transformed into a scenic narrow rail lined pedestrian walkway (hike-a-bike) path that traces the Kill Brook ravine and the Kill Brook.
It's a wonderful photo-op opportunity. The trees cling precariously to rock walls, water cascades over stone steps and rocks, Tthe path passes under the unusual Sing Sing Kill Double Arch Bridge designed by John B. Jervis, a 19th century Civil Engineer. The first arch was built in 1842 as a single 88-ft wide arch runing in a north-south direction to carry the Aqueduct 100 feet above and over the Sing Sing Kill and ravine. Later, in the 1860's a second arched bridge running east-west was threaded through the first arch to carry Broadway across the gorge resulting in the impressive double arches.
Lower parking lot of the Joseph Caputo Community Center located at 95 Broadway, Ossining, NY where ADA accessible ramps lead down onto the path or via the Central Avenue Bridge staircase.
Aqueduct Weir Tours at Ossining
Guided tours are available where you will watch a short film and afterwards take a short walk to the Weir on the Double Arch Bridge. Then you will descend into the original 1842 brick water tunnel and learn all about the history of the Croton Aqueduct from inside out.
For Tour Schedules Contact: Friends Of The Old Croton Aqueduct
Historic Districts & Architecture Bike / Hike Walking Tours
The Downtown Ossining Historic District was listed on the National Register of Historic Places in 1989. It is one of the few downtowns in Westchester County where its social and historical development remains intact. The district is located roughly along US 9, Main St, the village's traditional business district known as the "Crescent", and Croton Ave. The district is very walkable, so you can easily hike your bike to discover some Hudson River Valley Town architectural classics.
The Crescent" gets it's name from it's curved profile of the buildings fronting the street as it winds its way down hill from it's intersection with Highland Avenue. Many of the commercial buildings were built during 1871 and 1914.
The Ossining Bank for Savings
Circa 1908. The Beaux-Arts style dome, it's unusual square historic "TIME TO SAVE" clock atop a stone column, and it's location at 3-way intersection makes this an Ossining landmark.
Location: 200 Main Street, at the intersection of Highland Avenue, Croton Avenue, and Main Street.
Lower Main Street
This quaint lower section serves as a link between the Crescent and the downtown waterfront. There are several really nice late 19th century historic buildings along this stretch between 107-113 and 127 Main Street. Continue walking down and onto Secor Road to visit the historic Ossining Train Station.
For more information download NPS Funded: Ossining Walking Tour Brochure
During the 1830s New York City was in dire need of a fresh water supply to combat the steady rise of disease and to fight numerous fires that often engulfed large tracts of businesses and homes. Construction of an unprecedented magnitude began in 1837 under the expertise of John Bloomfield Jervis. The proposed plan called for a 41 mile aqueduct and dam to be built in order to run water from the Croton River to New York City. Three to four thousand workers, mostly Irish immigrants earning up to $1.00 per day, completed the masonry marvel in just five years. In 1842 water flowed into above ground reservoirs located at the present sites of the New York Public Library and the Great Lawn of Central Park. Throngs of people attended the formal celebration held on October 14th and celebrated with "Croton cocktails" - a mix of Croton water and lemonade.
Up The River
The expression "up the river", used to describe someone in prison or headed to prison derives from the practice of sentencing people convicted in New York City to serve their terms in Sing Sing. Located along the Hudson River on the Ossining downtown waterfront, this maximum security prison was the 5th prison built by New York State. It has a history and visitor's roster that will literally frizz your hair.
Sing Sing Prison Museum
Sing Sing Correctional Facility is a working prison facility where the theories and realities of criminal punishment and rehabilitation have played out for almost 200 years. There are plans to convert a circa 1825 cellblock into a museum. The project is spearheaded by the Historic Hudson River Towns (HRRT).
No sweeping this under the Croton Aqueduct Trail. Fascinating history that will "DARE YOU NOT TO LOOK AWAY."
For more information: Sing Sing Prison Museum
By Car: Croton Gorge Park - Take Route 9 north or south to Route 129. From Municipal Place turn left onto Maple St. Continue north on Maple St. (Rt. 129) merging with Grand St. and eventually becoming Yorktown Rd. Turn right at sign for Croton Gorge Park (fee). Park at the far end of the parking lot to access trail. Limited parking can also be found along several streets where the trail crosses the road.
By Train: Easily accessible by public transportation and it's proximity to New York City makes Croton Aqueduct Trail the perfect day trip. Bring your bike along for the ride on The Metro North Hudson Line. It provides train service to towns all along the trailway from Grand Central Station in NYC.
Tip: An excellent detailed, accordian-style map of the entire trail is available from Friends of the Old Croton Aqueduct. It can be purchased at Park Headquarters in Dobbs Ferry, the Rockefeller Preserve or the Visitor Center in Ossining and other locations. Because some offices may run out of copies we recommend ordering it from their website.
Old Croton Aqueduct State Park
Phone: (914) 693-5259