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Aacole gave a good summary. Middletown is horrible. My ex used to drive from LaGrange to Middletown for work every day because we wanted to keep the kids in Arlington schools, where we had also graduated from. You will be hard pressed to find a better school district than Arlington, except for perhaps Spackenkill.
Ulster, Orange, Putnam (obviously Dutchess), and part of Westchester counties will be a breeze for him. He will learn to love/hate the Taconic Parkway. Remind him not to speed too much on it, the police love giving tickets, just ask my dad, who traveled from LaGrange to Westchester every day for 20 years lol. If you situate yourself, keeping the Taconic Parkway in mind, you and your family can be anywhere very quickly, even into NYC itself. You'll also be on the prettier side of the aformentioned counties, imo.
Stay away from: the CITY of Pougkeepsie (heavy heavy drugs), Beacon (same) & Newburgh.
The TOWN of Poughkeepsie is broken into different school districts, some go to Arlington, some go to Spackenkill. Spackenkill has generally higher priced homes (not always), but a superb school district, especially elementary.
As a person who was raised in LaGrange from 10 yrs old to 36, I wish I never left. I'm in SC now, and I really do NOT like it. 0 culture like I'm used to. You'll have a whole new world open to you with NYC a little over an hour from you. Huge museums, Chinatown, Bronx Zoo, shopping galore, Radio City Music Hall...you name it. 1 1/2 hours north you have Albany...more (smaller) museums (visit the state museum, the kids will LOVE it), great places to eat. Ok, I don't miss the snow or the cold winters.
Oh, and you MUST MUST MUST visit Adams Fairacre Farms on Rte 44 on the Town of Poughkeepsie/Pleasant Valley border. Huge farm style market, where the prices of fruits and veggies will keep you wondering why you paid such high prices in the SOUTH for such things (this still baffles my mind every time I go to the store).
Trust me...you'll love it there. I miss it terribly.
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