Shaianne my greyhound who all but one time - the only time she was "loose" was an accident! I took her to a ball diamond once but was so nervous that even tho it was enclosed I stayed right behind her the entire time and she never even knew she was offleash!
Keegan on the other hand is usually pretty good unless a neighbor is out and she goes visiting. My parents call her the neighborhood PR person.
At their house they have 3 acres so she is rarely on the leash at their house. If we are taking a walk - she is on leash.
At my parents cottage - if we walk I have her leashed - now my dad can take her for a walk down the road and have her off leash and you couldn't tell it - she stays right by him and listens. She knows she has too. Me - PUSHOVER - ehh not so much. So I don't chance it - when we take walks unless its in the middle of a trail or woods - she is leashed.
I would try some of the local schools or parks if they have baseball diamonds fenced in - just make sure you clean up after him to be a good "neighbor".
Does Kenny like to retrieve? that is another incentive - if we go walking at the resevoir I usually keep a couple balls with me b/c she just LOVES tennis balls and keeps focused on them so she doesn't go far. I've even take them to the vet before!
Also Keegan is 5 years old but with her bilateral hip dysplasia - she doesn't run off much anymore **((knocks on wood))** b/c after awhile her hips get tired and she lays down.-
having a big dog is so much fun. I mean you can do all of this with a little dog but romping in a field isn't the same. And the only reason I say this is b/c my neighbor is an avid hunter and they have a 10 pound shih tzu and he has tried taking her with him before just to check his stands and she can't jump over the fences or gets stuck in the weeds - and her hair is so long then he has to spend an hour brushing the cockleburrs out of her coat when they get home (or catch h-e-double hockey sticks from "mommy" ). Zoe the shih tzu LOVES to go with daddy but he has to pick her up and carry her half the time.
good luck and have fun