Raleigh, NC to Montpelier, VT--first timer

I am planning a summer road trip from Raleigh, NC, to Montpelier, VT...MapQuest puts it at 805 miles. After reading a wealth of information from this site, I will shoot for 500 miles the first day which will put me somewhere around Hutchinson River Parkway and I-95 (just crossing over to Connecticut).
I am a "solo" driver traveling with 3 young children. A few questions:
How do you plan out the trip; i.e., Do you make hotel reservations & how/where or do you drive until you pull off the interstate and hit any hotel in the area?
Is there a way to find some "fun" stopping spots along my route for the kid's to stretch their legs?
Is MapQuest enough (it is pretty much all interstate driving) or do I need a map for each state?
Any tips for a first timer will be appreciated. Thanks!

Welcome aboard the RoadTrip America Forums!

Tonight seems to be the night for first-timer's! Great to have you all here! For some general planning tips, start by reading this thread. As to your specific questions:

Whether or not to make reservations or just pull off the road for the night when and where fatigue strikes is a matter of continuing debate, even among seasoned RoadTrippers. Everyone is a bit different. In your case, travelling with 3 children and wanting to bed down in the New York metro area, I think that the uncertainty of playing it by ear, as well as being left to try to find accommodations while driving congested roads would tip the balance towards making a reservation for that first night. You might also want to consider some alternatives to driving through New York City (skip down to about the 9th message).

I am a proponent of keeping things simple for young children when travelling by car. They'll be happy just to get out of the car and run around for a while. State parks are a great resource for this when driving. They are marked on most maps, and you can get a pretty good idea of what's available along your route by checking each state's park website - just 'Google', for example, Virginia state parks, and see what's along your route.

MapQuest is fine for planning, but when actually on the road a good set of individual state maps, or an atlas, is pretty basic equipment. It will also help keep the older children involved in the trip if they can help pick the stopping places and be 'responsible' for charting the progress of the trip.

AZBuck

Okay, I am a FIRST-TIMER, traveling with 3 kids and I am going to do "it"~~a ROAD TRIP that is! I am looking for interesting stops between New Jersey Turnpike and New Haven, Conneticut. I have my routes AROUND New York City as needed and the way to search out State Parks.
Are there any MUST SEE ATTRACTIONS for us on our travels?
No water/theme parks; but kid's activities and history?
Or any decent hotels near New Haven with a pool?
Thanks for your thoughts!

HI, Traveling with my three kids (9,8, and 4) and mother (75) from Vermont to Wells Beach, Maine. Any MUST SEE'S or things to do ALONG THE WAY or, more importantly, in and around WELLS BEACH, MAINE??? Lighthouses, Salt Water Taffy Pull Stores, Tidal Pools/Beaches, etc.??? No theme parks/water parks...pure family "fun"...Traveling Aug. 2-5, Thanks!

Unfortunately, the New Jersey and Connecticut coasts are fairly built up in the New York metro area, but still there are a few quieter venues appropriate for children and with an historic or educational bent, including the Stamford Museum & Nature Center is in Stamford, Earthplace in Westport, and the Shore Line Trolley Museum in East Haven.

Just south of Hartford on your drive up to Vermont, there is a unique state park where, if you bring your own plaster of paris, your kids can make there own casts of real dinosaur footprints. Finally, there is a ton of stuff in New England. Here are some links to some of those that I generally recommend.

AZBuck

If you're looking for quirky places to entertain the kids, be sure to check out this site before you leave. Generally I agree with the previous idea, the best way to entertain couped up kids is just to pull over at a state park (stop at the state visitor center if you see one as you enter each new state and pick up a brochure) or a good playground (pull in to any decent looking area and ask for directions to one) and let them run around til they tire themselves out!