Hudson does take out of district players, they had Kyle Turner and Zach Hunnewell a couple years ago when my son played there. Their Sr. district includes Hudson, part of Litchfield, and part of Pelham. Every year since the Jr. program has started, Hudson has qualified for playoffs - they and Dover are the only two with that distinction.
In case you don't already have it, Hudson's website is:
http://www.hudsonpost48baseball.com/ Rick Harvey does a great job keeping it up to date and he will answer email/questions you may have.
In the couple years I was there tryouts were always well attended and they cut quite a few players. This past year, although my son was offered a spot on the Hudson Jr. team again he preferred the Central Orange team. Play time opportunity (to pitch primarily) and the coaches he talked to during tryouts.
As with anything - ask your questions before you commit to the program. Your son needs to know what he wants out of the experience. If the roster is top heavy (more 16/17's w/ more experience), will your son get the chance to play enough innings to make it worth it. Two years ago, one player played both Hudson Jr. and Pelham Sr. Babe Ruth. Also, not sure who will coach the Hudson team this year. For the last two years it's been John Brun, but his son will be on the Sr. team only next year. His primary assistant's son is also too old for Jr. ball. Prior to that, Dave Lelievre (Korey's dad) was the coach. If the pattern holds, then my guess is they go with a dad again and more than likely, it'll be Jeff Hurley.
Finally, I don't think it's been mentioned yet, but there's a Jr. team in Milford too as another option.