After trying this a few times and getting lost because of some trickiness on the lower end – including an unexpected trip on the Van Cortlandt golf course and crawl through a fence with a friend – I found the key to a loop involving the Southern Portion of the OCA with the Putnam Trail. This is the course that the Van Cortlandt Track Club takes on Saturday mornings, although they start from the southern end. Also, there are water fountains off the path at Tibbetts.
The Putnam Trail is a remnant of what was ultimately the Putnam Division of the New York Central Railroad, and its chronology deserves its own page, which it has.
If you look at this Audubon Society map, the entrance is where “Exit Ramp” meets Midland Avenue. The OCA is the dashed brown line. The path into Tibbetts is the dotted black line.
From Westchester, I park on Yonkers Avenue in front of the Dodge dealer. The meters are $.25/20 minutes, but if you hit the button before putting your money in, you get an extra 10 minutes. NOTE: Yonkers enforces meters until 7:00pm. I’ve never had problems parking there.
Walk down the hill to the traffic light right before the bridge. If you are standing looking at the bridge, the entrance is across Midland and to your left, just to the left of the exit ramp from the Cross-County. There is a paved path with a sign directing you to Tibbets. Follow that path down the hill. (For the OCA: Southern Portion, you take the left into the clearing about 20 yards in.)
The Putnam Trail cuts through Van Cortlandt, and is ultimately just to the east of the Henry Hudson/Saw Mill River Parkway. It continues up into Westchester, and in Yonkers becomes the paved South County Trailway [this is a PDF link from the “Bronx River Pathway” link]. But south of Tuckahoe Road, it is dirt; it’s the railroad bridge under which you drive just at the western end of the Cross County Parkway.
It is a really bad trail for most of its distance until you reach Tibbetts Brook Park. If you are going to run it, bring a machete and watch for the drops. I ran this a few times with friends from Bronxville, and one of us got whacked to the ground by a tree-branch. I suggest avoiding this.
But the trail becomes quite nice when it reaches Tibbetts Brook. There is a wire fence that separates the trail from the Park. For purposes of the loop-run, you enter from Midland Avenue as you would for the OCA: Southern Portion. Instead of turning left into the clearing, however, stay on the paved path and go down the hill. It takes you to a road at Tibbetts Brook. Here’s a map of Tibbetts. On the map, it’s a counter-clockwise loop starting at the end of the dashed-line in the upper right-hand corner, and you get off the paved path just before it turns east again at the lower left-hand corner.
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The map shows how easy it is. The following describes the Tibbetts portion: From where you split from the OCA entrance, when you get to the path, turn right and then go left in a counter-clockwise circle. It’s a little tricky, but you then need to follow the still-paved path south, just to the left of the tennis courts and then to the right of the lake. Just before the path turns to the left, keep going south on the grass – it’s wide – and you will shortly see a path to your right perpendicular to where you are. Take that and it brings you to the Putnam Trail in about 20 yards. Turn left.
The Putnam Trail is a bit windy for a short bit, so tread carefully. It then opens up where it goes under the bridge (which is McClean Avenue in Yonkers). Just follow it south. When you get to the lake on your left (the fields of Van Cortlandt will be up and to your right), follow it around.
This leads to the entrance to the golf course. Cross the road, and hook up with a marked NYC Greenway trail, this for Mosholu/Pelham Parkway. The path has a white-line down its middle, as shown in the picture. (The path for golf-carts will be to your left.) Follow it. There is a small clubhouse to your left with bathrooms. Instead of crossing the strret, you can run by the lake, which takes you past the club-house and up to the First Tee. Right past the First Tee (on your left) and after you go under a bridge, the Greenway path does a hairpin turn to your right. Don’t take it. (I made that mistake.) Instead, you will see an old, wide stone staircase right in front of you. Climb, taking care of some loose stones. It takes you to the Major Deegan Expressway. Just follow the still paved path away from the Deegan and up into the woods. You will see an unpaved trail to your left; take it. This is the end of the OCA: Southern Portion. Then just take it straight-north until you reach the end.
The only other tricky stretch is towards the end. You go under a bridge (which is the entrance to the Tibbetts parking lot) when the trail is paved. Keep going straight back onto the trail when the paved-path starts down the hill into Tibbetts. This takes you up to where you came in or, if you started from the south, takes you to where you make the left down the hill into Tibbetts, which you’ll recognize when you hit a paved path just to the left of a faded-yellow building.
If you miss that turn, you’ll eventually be forced back to the OCA (which will be to your left), so just go with the flow.
Since it is a circle, this trail can also be picked up from the south. To get the stairs just mentioned from the Van Cortlandt flats, and from the 1 or 9 train, you enter the flats and run across the southern end, with the fields (or pitches) to the left, and several buildings to the right. As you approach the end of the fields, there is paved path to your right. Follow it and to your left you will see an unpaved trail with a number of low, vertical logs preventing vehichles from entering. This goes directly down (not a steep hill) to the right of the lake. You will cross the Putnam Trail. Then just follow the above instructions. The road is the entrance to the golf course. Cross it, and go to the left, on a paved path with a white line down its center. Follow it under a bridge – the first tee is to your left – and before you would otherwise take a share hair-pin turn to the right, continue straight, and you will find the stairs I mention. You then head straight up the OCA.
This stretch is narrow and after you pass a Wier (which is a stone building used to control the level of the water) it becomes rocky, so care is required. This narrowness and rockiness will end, however, when you hit the Westchester border, which is marked when you pass through a low wooden fence. Shortly after that, you cross a street, so use care, and then shortly after that you cross McLean Avenue, which is a busier street requiring particular care. But those are the last streets you cross on this run. The trail is wide with good footing the rest of the way.
You hit a paved stretch that narrows and goes under a bridge over which cars entering the entrance to Westchester’s Tibbetts Brook Park drive. After that, the paved path goes to the left and down a hill, but you should veer to the right to stay on the OCA. You will see the second of two ventilation towers and ultimately a stone building. At that building, the OCA segment ends. (The OCA trail disappears for about a mile as it heads to the west, to be picked up again further up in Yonkers.)
You can also get to the trail via the 4 train to Woodlawn. I did this once when I was lost. You continue along Jerome Avenue, with Woodlawn Cemetary on your right. There are 2 ways to go from here. The easiest way is to cross the bridge across the Deegan Expressway, but I still must get the particulars for this.
Stay to the southern side on the bridge. There is an opening to your left; in the picture it’s to the right of the tree, with the trail going between the two metal posts with the red marks. Follow it down a slight hill with a narrow path. You will hit a trail at the bottom, and turn right. Follow it, bearing left at a fork. (If you take the right, it takes you back towards the Deegan, and if you go that way, turn around, and take the right-turns when you have the option.) There is a rocky downhill stretch, which hits the OCA at a “T.” Turn right, and it takes you up into Yonkers.
The other is to turn right at the traffic light that has traffic coming off the north-bound Deegan. This is 233rd Street. Take the first left, which is Van Cortlandt Park East. You want to be on the left (north) side. There will be a driveway into the park. Take it, and follow it. Technically, at this point you are on the John Muir Trail and this link gets you to a really cool Parks Dep’t Map with an interactive map. You follow this. When the roadway goes to the right, go straight onto the unpaved section and then under the Deegan. Keep on this trail to your right, and it takes you down to the OCA, as just described.
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On the way back, the simplest thing is to keep your eye out for the path to your right after you pass the Wier. If you miss it and hit the fence into Westchester, simply double back.