local dog park might be your only bet.
At the peak of Mt Greylock last fall most of the dogs were on leash but once you start hiking most of the dogs that were on the trail going up/down were off leash and no one said anything. It was very refreshing. My dog is taller so we have a hiking vest with a handle on the back, just in case you come across weirdos that don't like dogs.
I'm not positive, but you can probably legally have your dog off leash on the Appalachian Trail once you get to National Forest lands in southern VT. You can reach it with a short drive, but I don't know about parking:
A longer drive will get you to the AT along VT rte 9 a bit east of Bennington, where there's good parking.
As post #2 notes, once you're into the woods you can probably let a well-behaved dog off leash as a practical matter even if it's not legal.
Most hiking trails in the area require a dog to be on leash; however, some areas of the AT may be a choice.
Rules for dogs on the AT are here:
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