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Whipporwill Valley Road

Whipporwill Valley Road, Middletown, New Jersey

explored & photographed by: Shady

I finally drove down this infamous New Jersey road one late November day (we were out just driving around getting lost for fun). It was right before sunset, and it was just as creepy and desolate as I had heard. When we first turned onto it, it looked like a nice normal paved road... I was like, heyyy, wait a minute! But it soon dropped off into a narrow, bumpy, darkly shaded dirt lane, and I was like... ok, this is more like it...

Whipporwill Valley Road

Whipporwill Valley Road

Whipporwill Valley Road

It's unbelievably narrow, and sewn in tight by the huge gnarled roots of the trees poking out along the edges of the road. Even the interlacing trees above block out most of the light. It's definitely a very isolated, lonely road. It's nerve-wracking because once you are on it, it's so narrow that there is basically no turning around or back, you gotta go all the way down it to the other end. We saw the legendary "I Know" sign, which I snapped a pic of; we also saw the mysterious road leading off into the deep woods.

Whipporwill Valley Road

Whipporwill Valley Road

Whipporwill Valley Road

We didn't encounter anything freaky, though... no KKK thugs, no Satanists, no handprints on the truck... nothing scary like that (the scariest thing was trying to avoid being run over by the RNs barreling up & down the road in their pickup trucks!) Then again, we were there during daylight hours (traffic was quite heavy on the road, even) I can only imagine that it's tons scarier at night.

 

Diggins of Middletown, NJ tells us, "I have lived in middletown basically my whole life. and i have heard many many stories about whipporwill. Ive have been on it maybe 50 times, it can be very strange when you are the only one on it. however many people go down it all the time. recently they have made an attempt to basically pave the road but it doesnt make it any better. if you are going to attempt to drive on this road i would say tou should head to the road from chapel hill road. when you enter from chapel hill you can go from whipporwill, then to copper road. copper road is a better whipporwill that acctually has a road called road x that connects to it. towards the end of the road is something called \"cry baby bridge.\" once off the road there is the chapel hill cemetry, the home of dancing jesus. out of everything in this area the dancing jesus is a must see, it is in the middle of the cemetry and when you flash its lights then turn them off the statue will dance. it is worth a trip but is not the scarriest place on this site. enjoy your trips."

Marianne writes, "You might be interested in this: In your pictures of Whippoorwill Road you have a picture of a stone entrance place. If you cross the stream and follow the dirt road, you will come to the remains of a gatekeepers cottage. Continue on and you will see the remains of a great estate "Auld House," walk to the left and you will see the marble inground pool and the overhead wisteria supports. "Auld House" burned down in either the early 70's or late 60's. My husband and I used to go there all of the time. The estate was owned by the Haskell Family who have another estate next door."

And K writes, "Just finished reading all of the stories about Whipporwill. Some mighty scary stuff. I live on the farm that borders Whipporwill Valley Rd and Cooper Rd, so I know first hand some of the crazy legends that surround this place. However, I do know some of it is true. I think I may be one of the only people who has an actual photo (UNRETOUCHED) of the wall of faces. The story behind the picture is interesting but too long to type now. Also, as for the crazy man/farmer that shows up in almost all the stories, he is the caretaker of the property (Woodland Farms) and he is a NUT. So beware of him, most of all, if you come down here to investigate the stories. I really enjoyed your site..."

Do you have any background information or stories to tell about an spooky road?

 

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