Bleg: New England Backpacking

As a test of an idea that Brogan kicked out today:

It’s a ways in the future, but I’m looking for suggestions for good places to get Jake hooked on backpacking. Here’s what I’d like:

– less than 2 hours from Hartford.
– Actual backpacking, not car camping.
– Preferrably something cool to do once the hike is over.
– Campsite not more than 3 miles from the trailhead
– Something cool between the trailhead and the campsite

I’m considering Pauchaug State Forest, just ’cause it’s really, really close to Mystic. Looks like Nipmuck State Forest has actual camping, too.

Other areas that I know are large and wild and close-by are Arcadia in Rhode Island (unsure about camping there; know the fishing’s great), and …

Is there anything like this in the Berkshires in Mass? I think the boy’s a bit too small to head up to the Whites in New Hampshire. And I love, love, love the Adirondacks in New York, ‘specially after going to prototype at Ballston Spa, but most of the places I’ve been up there are a pretty good ride in the car, which I think might kill interest on the boy’s part. And completely would rule out taking the two-year-old.

Thanks in advance, Internet. You’re the greatest.