Sleepy Hollow to Dobbs Ferry

One of our members, Carlos Gee, has walked the entire length of the Westchester trail (thereby earning a PATCH!). His excellent blog, Scenes from the Trail, recounts his multi-day journey, with helpful tips and photos of what he saw along the way. He was kind enough to allow us to reproduce his blog entries on our site. Thank you Carlos!

September 24, 2016 – Sleepy Hollow, NY to Dobbs Ferry, NY

Difficulty: easy

Length: approximately 6 miles

Route type: linear

This is the third leg of my section hike on the 26 mile Westchester County portion of the Old Croton Aqueduct Trail.

Another beautiful day for hiking on this September morning. Temperatures were in the low 70’s and no rain. We parked one vehicle at Mercy College in Dobbs Ferry, which would be our ending point and drove back to Gory Brook Road in Sleepy Hollow where our hike would begin.

editor note: You could take Metro North to Sleepy Hollow and walk uphill to the trail. At the end of this walk, the Dobbs Ferry train station is accessible if you continue past Mercy college into Dobbs Ferry Village. You could visit the Keeper's House Visitor Center and then walk downhill to the train station.

Gory Brook Road

After parking the vehicle, we walked towards the chained off Section of Gory Brook Road (above) and turned left onto the Old Croton Aqueduct Trail. We began our hike by proceeding south along the trail.

Old Croton Aqueduct Trail – Sleepy Hollow

We walked past the gate onto Gory Brook Road.

Old Croton Aqueduct Trail – Sleepy Hollow

The gate has the OCA lettering on it which is a nice touch.

Old Croton Aqueduct Trail – Sleepy Hollow

Crossing the road, we encountered ventilator shaft 12.

ventilator shaft 12

As always, the aqueduct is a nice easy, mostly level walk.

Old Croton Aqueduct Trail – Sleepy Hollow

After a short walk, we crossed over Bedford Road and into the Sleepy Hollow HS parking lot.

Old Croton Aqueduct Trail – Sleepy Hollow

The OCA trail goes through the back lot of the school which is evident by the sign.

Old Croton Aqueduct Trail – Sleepy Hollow

When we reached the end of the parking lot we turned left and walked along the side of the high school. When we reached the back of the auditorium we turned right at the rear of the building, bordered by a fence and the school.

Old Croton Aqueduct Trail – Sleepy Hollow

We followed the blacktop around the back of the school until we were walking towards the cafeteria and once again on the aqueduct.

Old Croton Aqueduct Trail – Sleepy Hollow

We crossed Cobb Lane and continued along the tranquil path, now in Tarrytown.

Old Croton Aqueduct Trail – Tarrytown

We crossed McKeel Avenue and Hamilton Place, then came to ventilator shaft 13.

ventilator shaft 13

After crossing Neperan Road and East Elizabeth Street, we came to East Franklin Street where the OCA trail veers right away from the aqueduct. We walked towards Route 9 and headed south along Broadway (Route 9).

East Franklin Street – Tarrytown

Broadway (Route 9) – Tarrytown

We walked on Route 9 until we got to Leroy Avenue and turned left.

Leroy Avenue – Tarrytown

There we caught up with the aqueduct which was on the right.

Old Croton Aqueduct Trail – Tarrytown

Walking along the aqueduct which was tucked between homes and businesses on either side, we continued on.

Old Croton Aqueduct Trail – Tarrytown

It’s always nice to see some wildlife on the trail.

Old Croton Aqueduct Trail – Tarrytown

We came to ventilator shaft 14, which is located right near Route 119.

ventilator shaft 14

The OCA trail once again veers right, away from the actual location of the aqueduct at Route 119. That is due to the construction of the NYS thruway, which cuts right through it. We crossed Route 119, turned left onto Route 9, heading south and crossing over the thruway.

Route 9 – Tarrytown

When we came to the Honda dealership, we turned left onto Walter Street and proceeded up to Sheldon Avenue. Walking past Short Street, the aqueduct is now visible on the right. We continued following the OCA trail and then crossed Route 9.

crossing Route 9 – Tarrytown

After crossing Route 9, we entered the Lyndhurst estate property. Along the left side of the aqueduct is the indoor pool building (also known as a natatorium).

pool building

The OCA trail cuts right through the property.

Old Croton Aqueduct Trail – Lyndhurst estate property

Lyndhurst is a beautiful place and it is where we took our first break. The grounds are very scenic and well kept. They also have a Gothic Revival castle.

Lyndhurst Castle

Lyndhurst Castle

We sat on a bench facing this majestic castle and enjoyed a bite to eat along with some refreshments. I have visited this property countless times over the years and always enjoy the tranquility that this setting provides.

Lyndhurst estate

After a pleasant break, we got back on the trail and almost immediately came upon ventilator shaft 15.

ventilator shaft 15

This part of the aqueduct which passes through Irvington, is bordered by some grand estate properties, some of which are no longer residential. Long ago, palatial mansions lined the Hudson River, most of which are no longer standing. We walked alongside a high stone wall with a barbed wire fence above it. On the other side of that wall was the former Belvedere property.

Old Croton Aqueduct Trail – Tarrytown/Irvington

Visible from the OCA is a brick tower with a cone shaped roof.

brick tower – Belvedere

After crossing over several Irvington streets, we came to Villa Lewaro, the former estate of Madam C. J. Walker. She was an African American entrepreneur, philanthropist, and a political and social activist. Eulogized as the first female self-made millionaire in America, she became one of the wealthiest African American women in the country. The estate is quite lavish to say the least, but from the aqueduct, you only get a partial view of the rear.

Villa Lewaro

Crossing Main Street, we arrived at ventilator shaft 16.

ventilator shaft 16

Along this stretch we saw some nice homes, a long and high brick wall and an ornate wrought iron fence.

high brick wall

wrought iron fence

We walked by the Nevis Estate, built by James Hamilton, son of Alexander Hamilton in 1835 and named after the West Indies Island where his father had been born.

Nevis Estate

As we approached our stop point, which was Mercy College in Dobbs Ferry, we came to ventilator shaft 17.

ventilator shaft 17

Once past the ventilator shaft, we entered the parking area for Mercy College and back to the vehicle. We drove back to Gory Brook Road and picked up the car we had parked there when our hike began. I hope you enjoyed today’s hike, I sure did. Don’t forget to follow my blog and stay informed about hikes in the Hudson Valley and beyond. Until next time folks, keep on trekking.

keep on trekking


NEXT: Dobbs Ferry to Yonkers