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In the late 90's, I had a quadruple header once. I was a medical laser equipment field tech for NY/NJ area and my travels ended up taking me to these 4 tracks (I went into each track after my work was completed in each area).
1st track was Monmouth, then to Aqueduct, then to Yonkers and finally driving home on the NJ Turnpike stopped at my 4th track, the Meadowlands for last race. It was a long day, but had about $200 profit. The funny thing is I tried to get to Freehold after Monmouth, but dispatch sent me to Yonkers area. It would've been 5 tracks in one day since i would spend a little less time at each to make all five.
I've had doubleheaders several times with a combo of Monmouth/Big M/Freehold.
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