I think I can save you a LOT of money in getting to High Point State Park.
1) Fly into a New York City Area Airport.
Newark / Liberty Airport would be the best.
2) Get to the Secaucus Junction via New Jersey Transit.
You can do this directly from Newark Airport.
Any other airport will require that you get to New York Penn Station.
3) From Secaucus Junction, ride a train to Port Jervis, on either the "Main Line" or the "Bergen Line."
https://content.njtransit.com/public...ap-Aug2022.pdf
Note that not every train on these lines go all the way from Secaucus Junction to Port Jervis -- make certain you get on a PORT JERVIS train.
4) It's five miles from Port Jervis to High Point State Park.
There are taxi services in the city, and I had no problem using one of them -- but it has recently gotten SCATHING reviews on Yelp.
Uber may or may not be a better idea.
As for gear in Port Jervis, this place may well meet your needs:
https://www.sawkillcreekoutfitters.com/
I do that as a kind of last hike for the year. I thought it was about 7 miles to the park headquarters.
Here's my blog from nine years ago:
https://www.whiteblaze.net/forum/ent...ter-Gap-Part-1