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The Breakdown

As the name implies, this off-road trail follows the right-of-way of the Old Croton Aqueduct. Find the trail in Sleepy Hollow and ride the first segment to Briarcliff Manor.

Pick up the trail in downtown Ossining and follow it north towards Croton.

Rejoin the trail in Crotonville and ride to its conclusion at the New Croton Dam.

Stretching across the Croton River and overlooking Croton Gorge Park, the dam marks the end of the Old Croton Aqueduct Trail in spectacular fashion.

Depart from the dam and ride sylvan local roads into Peekskill.

Wrap up your ride with some eats and a few Peekskill specialty brews. The brewery is conveniently located a stone’s throw from the Hudson River and Peekskill train station.

Tarrytown to Peekskill

You’ve fled north and escaped the confines of New York City. You’ve discovered Van Cortlandt Park and the South County Trail. Your legs have taken you as far as Tarrytown and Sleepy Hollow. So where to next?

Another 20 miles, at the northern edge of Westchester County, elbowed into the eastern shore by a dramatic bend in the Hudson, lies a city known for its inspiration behind L. Frank Baum’s famous yellow brick road and backdrop for the 1980s sitcom, “The Facts of Life”. The city, of course, is Peekskill, NY. In addition to being the birthplace of Mel Gibson, Stanley Tucci, and Paul Reubens, Peekskill is also one of the best cycling destinations that’s within a day’s striking distance of New York City.

But what truly makes Peekskill a great destination – what makes any destination great – is how you get there. In this case, how you get there is largely accomplished via the Old Croton Aqueduct Trail (OCAT).

The OCAT is a peculiar mélange of earthen trails that passes through tree-lined canopies, grassy meadows, village centers, and suburban backyards. The roughly 25-mile network of trail begins in Yonkers and ends at the New Croton Dam in Croton Gorge Park. The trail follows the right-of-way of the Old Croton Aqueduct which acted as New York City’s supplier of water from 1842 – 1955. After making the 40-odd mile journey from Croton to the city, the water was deposited into two above-ground reservoirs in Manhattan. Today you might recognize these sites as Central Park’s Great Lawn and the New York Public Library on Fifth Avenue.

If you’re interested in a more detailed history lesson, you can visit the Friends of the Old Croton Aqueduct. The Friends are a non-profit society dedicated to the protection and preservation of the aqueduct. Their website is a good resource for historical and current information regarding the aqueduct and the surrounding area.

And for a more intimate and introspective reflection, NYC-based artist and urban explorer Miru Kim has documented and photographed the aqueduct from the inside. In the nude, obviously.

As previously mentioned, the Old Croton Aqueduct Trail has its beginnings in Yonkers. The trailhead can be found near the intersection of Ashburton Avenue and N. Broadway, not too far from Yonkers Station. However, due to several factors of convenience, I personally recommend riding the South County Trail to Tarrytown and picking up the OCAT in Sleepy Hollow.

Either way you choose to go – once you arrive in Tarrytown – the Old Croton Aqueduct Trail becomes something of a necessity for continuing north. If you were to look at a map, it would appear that Albany Post Road (Rte 9) is the most direct link between Tarrytown and Peekskill.

And it is. For cars.

But once you get north of Sleepy Hollow, Rte 9 increases its speed limit, turning into a dicey thoroughfare with a high volume of cars and no substantial shoulder for bicycle traffic. So despite some of its unconventional characteristics, such as an unpaved surface and frequent crossings, the Old Croton Aqueduct Trail provides a safe and scenic alternative to Rte 9.

However, it should be noted that road bikes with thin tires will not fare well on the OCAT’s relatively rough-hewn surface. The trail is best-suited for mountain bikes, hybrids, and road bikes with tire width that can handle the varying terrain which shifts between hard-packed dirt, hard-packed gravel, loose gravel, and grass.

Speaking of grass, the greens really come alive on the trail during the late spring and summer. As do the insects. Sections of the trail are nothing more than narrow dirt paths beset on both sides by knee-high weeds and grass. There are plenty of deer in the area, which means there are also lyme disease carrying-deer ticks. Not to discourage traveling the trail during the bright and beautiful spring and summer, but if you do choose to ride during the tall grass season, exercise caution and stick to the path. The autumn, on the other hand, with its cooler temperatures, naturally manicured grasses, and explosion of changing colors, is the perfect season to explore the trail.

Regardless of which month you ride, after tackling the length of the Old Croton Aqueduct, you’ll be remunerated with dramatic views atop the New Croton Dam. From here it’s about a one-hour ride on back roads into Peekskill where you’ll find the welcoming Peekskill Brewery just steps from the Metro North train station.

Old Croton Aqueduct Trail: Part I

Tarrytown to Briarcliff Manor

Though a moderate ride that can be accomplished in a day from NYC, let’s begin the journey in Tarrytown at the corner of N. Broadway and Neperan Road since this is where the NYC to Tarrytown ride concluded. From here it’s about a 20-mile pedal to Peekskill.

As you may recall, Sleepy Hollow, formerly known as North Tarrytown, is just a few blocks north of the Neperan/N. Broadway intersection. After descending Neperan, turning right on N. Broadway points you in the direction of Sleepy Hollow. Less than a mile up the road, you’ll pass Beekman Avenue on the left and see Bedford Road (448) climbing uphill to the right.

An entrance to the Old Croton Aqueduct Trail is located a short distance up the hill on the left side of Bedford Road. Look for the wooden sign posts displaying “OCA”. If you pass Webber Ave, you’ve gone too far.

This first section of the trail is easy riding – flat, level, smooth hard-packed dirt. After less than a half mile, you’ll encounter the first of many local road crossings that intersect the trail. Follow the OCA signs to reconnect.

As the trail forges north it passes a section of the Sleepy Hollow Cemetery on your left. Shortly thereafter, the trail’s surface changes from smooth hard pack to loose gravel for a little less than a mile as it runs parallel to Rte 9. The path then turns left and follows a small footbridge that crosses Phelps Way. Here you will also find an entrance to the Rockefeller State Preserve on your right, though the preserve does not allow bicycles.

A bit further up the trail there is another footbridge which crosses over Albany Post Road and leads into the village of Briarcliff Manor. For about a mile the trail passes through this affluent suburb and, at times, literally cuts through residential backyards. Simply stick to the trail and follow the signs.

You will shortly arrive at River Road which marks the end of the first leg of the Old Croton Aqueduct Trail.

River Road

Old Croton Aqueduct Trail: Part II


As the Old Croton Aqueduct Trail comes to a transitory pause at River Road, an OCA sign directs the rider to the left. Rte 9 is to your right and straight ahead is the William T. Barnes building of The Clear View School.

River Road, as the name suggests, runs alongside the Hudson. This particular hamlet of Briarcliff Manor, swaddled between the river on one side and the Sleepy Hollow Country Club golf course on the other, has no shortage of luxury homes with impeccably manicured lawns. Those on the left side of the road especially, command boundless views of the river and Nyack Beach State Park across the water in Rockland County.

At its apex, River Road intersects with Scarborough Station Road which climbs eastward, away from the river and back in the direction of Rte 9. Continuing straight down the hill leads to Scarborough Station itself which sits at river level. River Road then passes the station and rises inland once again, as it changes its name to Kemeys Ave/Locust Road.

A left onto Revolutionary Road and another onto Rockledge Avenue will put you on Spring Street which shoots north towards the Downtown Ossining Historic District. As you pedal up Spring Street, the Sing Sing maximum security prison lies doggo beyond the row of houses to your left. The prison sits downhill at river level on the pragmatically named Correctional Facility Road.

If you happen to be a dark tourist looking to snap some photos of the facility, you’re best bet is to hang a left on Lafayette Ave off of Spring Street. There’s a small parking lot at the end of Lafayette that overlooks prison property. Venturing down to Correctional Facility Road is probably not worth the trouble as it’s bordered by a 12-foot concrete wall with three manned crow’s nests. Not to mention you’ll have to climb back uphill to Spring Street and my general experience has been that prison security is not appreciative of amateur photography.

As you make the climb up Spring you’ll soon arrive in downtown Ossining. Just before Main Street you’ll find Maple Place which is where the Old Croton Aqueduct Trail recommences. Main Street leads back to the river and Ossining Station where there is train service back to NYC. And if you’re hungry, the unassuming Paradise Mini Market on Spring serves up a miscellany of rice, beans, pork, plantains, stews, and other dishes that are alimental and merciful on the wallet.

A very short distance up Maple Place you’ll spot a red-brick path on the left. The path, adorned with benches, lampposts, and planted trees, feels more like a public plaza than a bikeway. However, this is the beginning of the second leg of the Old Croton Aqueduct Trail.

As you navigate this paved section of the path through downtown, you’ll promptly pass the historic First Baptist Church of Ossining at the Main St/Church St. intersection. A bit further up, you’ll cross the Sing Sing Kill Bridge and arrive at a 130-year-old weir chamber. This weir chamber is one of several stone buildings that allowed the managers of the aqueduct to control the flow of water at times when the aqueduct needed to be emptied for inspections or repairs. There are also tall distinctive, cylindric structures of ashen brick that occasionally mark the trail. These are old ventilating towers that were constructed every mile or so to alleviate pressure and keep the water in the aqueduct fresh.

Across the road from the weir chamber is an incommodious flight of steps on Ann Street that must be ascended in order to continue on the OCAT. At the top of the steps, the path continues in its paved state for several hundred feet before once again returning to its element of natural dirt and grass.

After a couple of more blocks, the trail will come to a brief halt on Snowden Avenue. Look for the continuation of the trail next to the Northside Firehouse. For the next half mile, as the trail runs east of Crawbuckie Park, you’ll pass by some tract housing which was under construction as recently as October 2013. Before long, the OCAT reunites with and once again crosses busy Albany Post Road, continuing for about a half mile until it is interrupted by Piping Rock Drive.

Piping Rock Drive is a very small residential side street, and would otherwise go unnoticed but for its obstructive location along the trail. On the south side of the street, the trail rises up steeply to meet the curb. On the north side, the trail descends sharply. So unless you have a rock-hopper or something similar, you’re going to have to dismount and either carry your bike up the incline, or walk it through some guy’s backyard in order to arrive at street level. From here, you can use your judgment, but if you’re on a road bike I’d imagine you’d opt to carry or walk your bike down the unwieldy slope. A tunnel bored below Piping Rock Drive might solve the problem but is an unlikely future addition to the trail. As it stands, this hitch is simply a minor impediment to the flow of the ride.

The OCAT continues north for a short distance until it meets Ogden Road. You will see an OCA sign directing you to the left. At first glance it appears that the trail continues straight ahead, but in fact it does not. If you were to go this way, after a few hundred feet it would run into NY-9A which is impassable. This marks the end of the second leg of the Old Croton Aqueduct Trail.

Old Croton Aqueduct Trail: Part III

Crotonville to the New Croton Dam

Follow the OCA sign and descend left onto Ogden Road until you arrive at the intersection of Ogden and Old Albany Post Road (not to be confused with Rte 9/Albany Post Road). Making a left here will point you in the direction of Croton Harmon Station and Croton Point Park.

However, in order to hook up with the third leg of the Old Croton Aqueduct Trail, you’ll need to turn right onto Old Albany Post Road. First you’ll pass beneath NY-9A and begin climbing uphill. After passing Reservoir Road and Gerlach Park, look for the entrance to the trail on the left.

Minus a couple of road crossings, it’s roughy 2.5 miles of undisturbed trail to the dam. A clearing punctuated with a succession of overhead power lines indicates that you are getting close. These power lines march northwest through the clearing all the way to the Indian Point nuclear power plant in Buchanan.

As you approach the dam, you’ll arrive at a sign that says, “Old Croton Aqueduct State Historic Park”, and the trail will split, with one offshoot sloping down to the left and the other remaining flat on the right. Keep to the wider, upper path on the right. This will escort you to the top of the New Croton Dam.

This marks the end of the third and final leg of the Old Croton Aqueduct Trail.

Riding the OCAT

New Croton Dam

End of the Old Croton Aqueduct Trail

As the Old Croton Aqueduct Trail emerges from the woods it terminates at Croton Dam Road which runs atop the New Croton Dam. This road is closed to all but emergency vehicles and pedestrian traffic.

The dam offers sweeping views of the New Croton Reservoir to the northeast. The Taconic State Parkway is visible in the distance as a faded red bridge crossing the reservoir. To the southwest the dam overlooks Croton Gorge Park and Croton-on-Hudson beyond.

Despite its name, the New Croton Dam is over one-hundred years old as it was built between 1892 and 1906. The Old Croton Dam is located in Yorktown, about three miles northeast of the new dam, and is only visible when the Croton Reservoir’s levels are very low.



Cortlandt & Peekskill

Local roads to the Peekskill Brewery

It’s about an 8-mile pedal through the town of Cortlandt from the New Croton Dam to the Peekskill Brewery. To get started, follow Croton Dam Road across the reservoir and find NY-129 after a few hundred feet. Croton Dam Road might have roadblocks set up to prohibit automobile traffic, but bikes are able to pass through.

In short, from here:

RIGHT on NY-129
Merge LEFT on E. Mt Airy Dr.
RIGHT on Colabaugh Pond Rd
Merge RIGHT on W. Mt Airy Dr
RIGHT on Furnace Dock Rd
Continue on Washington Street

These roads are largely quiet, with the exception of NY-129. It’s a brief stretch of road, but it’s worth noting that this area of the 129 has speedy traffic and riders need to negotiate the left-hand merge onto E. Mt. Airy Dr. carefully. This is because the merge is located at a blind bend, and traffic can materialize quickly from the opposite direction when bearing across (see photos).

Colabaugh Pond Road ambles around its eponymous pond and continues for two miles until joining W. Mt. Airy Dr. It’s soon a right onto Furnace Dock Road, which after less than a half mile splits to the right as Washington Street forges straight ahead.

Washington Street traces the western edge of Blue Mountain Reservation for several miles before entering the city of Peekskill from the south.

Kindly direct any comments, questions, updates, restaurant recommendations, praise, or cathartic rantings to velotrope@gmail.com.

The Peekskill Brewery

Washington Street makes its return to civilization after crossing Welcher Ave into the city of Peekskill. From here a few twists and turns on residential side streets lead to the riverfront, the train station, and the brewery.

Peekskill Station is located on Railroad Avenue next to Riverfront Green Park. The waterfront was transformed into a public space in the 1970s and provides nice views of Peekskill Bay. Jones Point and Dunderberg Mountain lie visibly across the water, as does Iona Island. Bear Mountain Bridge is hidden by a bend in the river just to the north. When looking at a map, the tectonic history between Jones Point and Peekskill is clear, the pregnant bulge of Jones Point like the last piece of a jigsaw puzzle fitting snugly into Peekskill Bay.

Located within stumbling distance of the waterfront and just across from the station parking lot is the Peekskill Brewery. Unfortunately, the brewery has no bike racks so I generally try and lock up to a street sign out front.

After hours of pedaling, the Peekskill Brewery is where you want to be. The beer is amazing, the selection fantastic, the food delicious, and the staff very friendly. The staff is also super knowledgeable and proud of their brew. If you have any beer-related questions you will receive a thorough education from your barman.

The brewery is set up on two levels with the tap room downstairs and a dining pub upstairs. However, since food and drink are both available in the tap room my preference is to grab a seat at the bar. If you’re with a group, there are several tables scattered around the tap room where you can sit.

Their house beer selection rotates but some of the standard-bearers include the Hop Common, Eastern Standard IPA, Amazeballs, and Crack of Dawn. If you’re lucky, they’ll be pouring their Dream of the 90’s coffee IPA. Brewed with coffee beans sourced from Tarrytown, the Dream is a good bet after dinner. Also be sure to ask about their cask beer on tap. The last time I was there it was the Chili Willie – a spicy cask ale brewed with jalapeños.

Of course, the location of the brewery is great, just steps from the Metro North railroad. When you’ve had your fill, mosey across the street to the station. Don’t forget your MTA bike permit. Or your bike for that matter.

Trains at night generally run about every hour back to Grand Central and the cost of an off-peak one-way ticket is $11.75.

You should be back in the city in an hour.

Tarrytown to Peekskill cue sheet


STARTING POINT: N. Broadway @ Neperan Road


Download PDF

mile: turn: street/trail: distance: Notes:
0.00 NORTH N. Broadway 0.7mi
0.7 R Bedford Road 0.2 mi
0.9 L OCAT 0.3 mi Old Croton Aqueduct Trail: Part I
1.2 X Gory Brook Road  –
1.2 S OCAT 1.5 mi
2.7 X Phelps Way 175 ft cross over footbridge, continue OCAT
2.7 S OCAT 0.8 mi
3.5 X Albany Post Road 50 ft cross over footbridge, continue OCAT
3.5 S OCAT 0.5 mi
4.0 X Country Club Lane 100 ft
4.0 S OCAT 0.4 mi End Old Croton Aqueduct Trail Part I
4.4 L River Road 0.2 mi
4.6 R Creighton Ln 0.2 mi
4.8 R River Road 0.5 mi
5.3 S Kemeys Ave/Locust Rd 0.4 mi River Road becomes Kemeys/Locust after passing Scarborough Station
5.7 L Revolutionary Road 0.2 mi
5.9 L Rockledge Avenue 0.1 mi
6.0 S Spring Street 1.1 mi Rockledge becomes Spring after Liberty
7.1 R Maple Place 230 ft
7.1 L OCAT 410 ft Old Croton Aqueduct Trail: Part II (look for red brick path on left)
7.2 X Church St & Main St 60 ft First Baptist Church of Ossining on right
7.2 S OCAT 0.2 mi Sing Sing Kill Bridge crosses over Broadway & Aqueduct Street. Stone weir chamber at end of bridge.
7.4 X Ann Street  – Must climb staircase at Ann St to continue on OCAT
7.4 S OCAT 0.1 mi
7.5 X N Malcolm  –
7.5 S OCAT 0.1 mi
7.6 X Van Wyck  –
7.6 S OCAT 350 ft
7.65 X/R Snowden Ave 230 ft Find OCAT to right of firehouse
7.7 L OCAT 0.2 mi
7.9 X Beach Road  –
7.9 S OCAT 0.4 mi
8.3 X/L Albany Post Road  – Find OCAT approx. 50 ft north of Audubon Dr
8.3 S OCAT 0.3 mi
8.6 X Piping Rock Drive  – Must either walk bike up to street level from trail or cut through backyard with swing set to street
8.6 S OCAT 0.2 mi End Old Croton Aqueduct Trail Part II
8.8 L Ogden Road 0.1 mi
8.9 R Old Albany Post Road 0.8 mi Old Albany Post Road becomes Quaker Bridge Road at Gerlach Park
9.7 L OCAT 0.9 mi Old Croton Aqueduct Trail: Part III (trail entrance a bit past Gerlach Park)
10.6 X Quaker Bridge Road  –
10.6 S OCAT 0.5 mi
11.1 X Quaker Bridge Rd E  –
11.1 S OCAT 1.0 mi End Old Croton Aqueduct Trail Part III
12.1 L Croton Dam Road 0.4 mi Cross the New Croton Dam
12.5 R NY-129/Lower Yorktown Rd 0.4 mi
12.9 bL E. Mt Airy Dr 0.2 mi Use caution merging across 129
13.1 R Colabaugh Pond Road 2.0 mi
15.1 bR W. Mt Airy Dr 0.3 mi
15.4 R Furnace Dock Road 0.3 mi
15.7 S Washington Street 3.7 mi
19.4 L Roosevelt Ave 0.1 mi
19.5 R Simpson Pl 0.3 mi
19.8 L Requa St 0.2 mi Pass beneath U.S. 9
20.0 R Railroad Ave 0.1 mi Peekskill Station on left
20.1 R Hudson Ave 100 ft
20.1 L S. Water St 350 ft
20.2 END 47-53 South Water Street END Peekskill Brewery on right
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