New York
Harriman-Bear State Park
New York has a great state park where you can actually hike through the woods all the way to the George Washington Bridge. I wouldn’t advise doing that but the state park is right outside of the Big Apple; beautiful, easy to get to, and full of deer. What makes it great is that you can hike out of the park on the AT and camp on a mountainside with the NYC skyline as your backdrop. Looking at NYC while surrounded by turkey, bear and deer is awesome in its own way. You can also hike in NY through a small zoo near West Point and then immediately cross the Hudson River over a large bridge straight back into a treacherously steep mountain. It’s odd being in a city and then being totally alone in a couple of miles.

Vermont
A world of it’s own. Everything is super green. Moose everywhere! I was even lucky enough to come face to face with a pine marten. Manchester Center is a great little town with a one-room theater (where I saw the final Harry Potter

). The green mountains are fantastic and the state has a very small population. I would recommend the Long Trail. Many New England’ers set out to hike the Long Trail; the oldest distance trail in the US. It’s 272 miles and 100 of those miles are on the Appalachian Trail. It’s awesome knocking out the miles of two trails at the same time. You could do a small section of the Long Trail on your yearly vacation and finish the whole thing in less than 5 years. There’s lots of ponds/lakes/streams and therefore beavers. Watch out for giardia.

New Hampshire
Franconia Ridge
My favorite AT state. If I had to do my 2,000+ miles again I would walk from Massachusetts to Maine and then back (known as a yo-yo---get it?). New England is insane and New Hampshire is the epitome. The Franconia Ridge, or Franconia Range, is one of my favorite places in America and certainly on the AT. There you will cross some awesome mountains (like Mount Lincoln and Lafayette). The fact that White Mountain National Forest is not a national park is unbelievable to me and yet freaking awesome because it means less people. There are huts that you can rent with bunks and cooks but I’m assuming they’re booked by now and you’ll have to wait until next summer. Also, they’re expensive and roughing it by backpack is more adventurous anyway. This is where I would go if I were you! You can knock out some of New Hampshire’s 4,000 footers—I plan to do them all before I die.

Mount Washington and the Presidential Range
This would be a cool trip because it is a highlight/landmark surrounded by ruggedness. The actual mountain has been bastardized at the top with a train, restaurant, and parking lot for the fatasses who can only get to the top by driving. That doesn’t mean that the hike up and down and the surrounding mountains aren’t insane. This is Lord of the Rings-level quality. For 76 years, until 2010, a weather observatory on the summit held the record for the highest wind gust directly measured at the Earth's surface, 231 mph. It snows every month of the year and never gets above 70 degrees. Hikers die here every single summer. Don’t hike in the rain or you will slip and regret it. Check out the Mount Washington hotel at the bottom.

Maine
Mahoosuc Notch
The Mahoosuc Notch is one of the hardest days of the entire AT. I'd argue it's the hardest. Some young guns do it in few hours, some old people take 2 days. It’s a feat of it’s own. You’re climbing over and under car-sized boulders towards the top of a mountain. There’s no shortage of remote, gorgeous places on the AT in Maine that I can point you to-- weird places like Rangeley... but I figured I’d start the introduction to Maine with the beast itself.

The 100 Mile Wilderness and/or Mount Katahdin
The name says it all: One hundred miles of trail with no towns or roads or ways out. This is a hiker’s dream. It took my friend (the author I mentioned in the AT thread) and I right at 5 days. Obviously we averaged 20 miles a day; which is nothing spectacular and speaks a good bit of the difficulty of the terrain. I carried 7 days of food just in case. You and your kid could do it in 7 and have fun. The area is on google maps if you’d like to see where it is. What makes it so great is that when you pop out on the other side you are at Baxter State Park (awesome place) and therefore only a short hike from Mount Katahdin, the northernmost terminus of the AT. The top, the end… or beginning if you’re a crazy south-bounder. You can always skip the 100 Mile Wilderness and hike up Mount Katahdin or spend a few days in Baxter State Park. I personally wouldn’t climb Katahdin without having hiked the entire AT first as that seems disrespectful and a way to ruin the magic of the trail if one or both of you ever decide to thru-hike. Katahdin is the light at the end of the tunnel but only for those who have made the journey to get there. Regardless, Baxter State Park is great on its own and worth checking out.

Non-AT Maine
Acadia National Park
One of the most underrated national parks out there. I’ve spent a couple of summers in Bar Harbor and it is a paradise in the summer. It’ll still be cool at night but will be awesome in the day time. Look up pictures of the breathtaking scenery. Mt. Desert is worth the air fare alone. Last time I was there Laura Bush was there because one of W’s daughters was proposed to on Cadillac Mountain. Great little towns and some of the best hiking in America.

The order I'd choose.
1. Franconia, NH
2. Acadia, ME
3. Estes Park, CO
4. Long Trail, VT

Google pics of the places I posted for generalities and ask for specific camp sites and pics of my travels for additional info.

I’ve done more hiking than just CO, WY, CA, ME, and the AT so feel free to ask away about a certain location and any hiking tips not in the existing, lengthy thread. I can also tell you about the good food & bars in each of the previous areas. Sorry it took me forever to do the write-up.
How old’s your kid and where does he currently live? I can show you places close to there that are great or some cool changes in scenery halfway across the country. PM me if I forget to check in on this thread. Thanks for unbanning me too.