Chicago to Bangor to Ft Myers advice and suggestions

As I sit here trying to recover from a knee surgery that went bad and I'm mad that we didn't get to go to Texas becasue of it, I'm starting to consider another trip my wife and I talked about and now seek suggestions. My plan would to leave Chicago about mid August and head to the Bangor Maine area for a few days and then head south to Ft Myers Florida. I'm just starting to look at places to see and need expert advice. We have a 34 foot 5er and like pull through sites and avoid cities when possible. I'm thinking Bangor and then head south to somewhere around New York City where I would leave my truck and trailer and take a train into the city. My bucket list includes the Statue of Liberty and the site of the World Trade Center. Our plans would include staying in the city for several days, maybe even getting on the Today Show. After which I'd like to head south preferably down the Applachian Trail. We need to be in Ft Myers October 1st so we're not in any big hurry.
Any advice would be appreciated.

Bob

I have a couple of ideas.  If you are not set on going straight to Bangor Maine from Chicago you may want to consider going north first, through the upper peninsula of Michigan, then down across the Mackinac Bridge to Northern Lower Michigan.  From there it's either across Canada - I prefer crossing at Port Huron and coming out at Niagra Falls, then across NY State into New England.

On the way back, you may want to look at Hammonasset State Park in Connecticut.  It's very easy to take a train to NYC from any of a number of small towns along the Connecticut shoreline.  Most of the towns along there (Old Saybrook, Westbrook, Clinton, Madison, Guilford, Branford) have train stations where the commuter trains stop and pick up/discharge passengers.  It's a fairly quick trip in to the city and back out again.  Hammonasset State Park is right on Long Island Sound, at Exit 62 off I-95.  There is a four lane connector from I-95 right to the Park Entrance.  Lots of campsites, great location, great beach, great local seafood restaurants, etc.  I grew up in Madison, and have been going back about every other year for the past 30 years or so.  I believe the camping fee is around 30/night or so - there is a website you can go to - just google "hammonasset state park" and you'll find it.  Campgrounds are few and far between in Connecticut, especially along the shoreline.

Another way to do this is to go to Northwestern Connecticut and try to find something, or up in the Catskills, which is about the same distance north of the city as Hammonasset is to the east.  Not sure of train service from there, but the trout fishing is good in the Catskills, or at least it was 20 years ago.

If you've got any questions about southern Connecticut I'd be glad to help.

Appalachain Trail is a foot trail, maybe yoy mean the Blue Ridge Parkway. If so, its a great drive as long as you are not in a hurry. Southern end has some pretty tight tunnels so I would suggest getting off near Maggie Valley.