A friend emailed me the other day and was looking for suggestions as she's headed with the family to some town I've never heard of called Conesus. It's above the Finger Lakes and below Rochester, and according to Google Maps, it's over 5 hours from NYC, with no stops. She was asking if breaking up the trip and if stopping in Binghamton would be a good way to do so....and rather than just email her back, I thought I'd turn this into a post, in the event that any of you ever find yourself going to Conesus for the weekend. Here are my suggestions:
Looking at Google Maps, it does have the most direct route as going through Pennsylvania. One thought, you could stop in the Poconos at the Great Wolf Lodge. This really has no impact unless your kid is at least 2, but it's big big impact if they're old enough to go. (Here's a link to my post about it.) Right down the road from there is a very cool soft-serve/hot dog kind of place, that has a helicopter swing set. You have to swing off the highway if just for that--it's literally a 5 minute detour. You can read my post about it here.
Along this route you also pass by Corning, which does have a cool glass museum that is worth checking out. It's actually the world's largest, and kids get in free!
As for breaking up the trip and spending the night, if the Poconos is too soon to stop, you could look around the Williamsport area as that seems somewhat in the middle. I usually just toggle between Google Maps, looking at the names of towns I will be driving through, and then googling places to stay in those towns.
Another way to go is to go via Scranton (the setting for The Office) and Binghamton. I wouldn't stay in Binghamton, as the hotels are super limited. It does have some good antiquing on Clinton Street, and it is home to something like 5 free carousels. And it has a great Discovery Center and Story Garden. I'd stay somewhere in Ithaca or Trumansburg, and check out my posts on that area. I haven't actually stayed in any properties around there, but in Auburn there are two nice hotels.
You should also see if there are any local county fairs going on if you're going up this summer. It's very likely that there would be one in some town you're driving near. We love the Grahamsville Little World's Fair and the Delaware County Fair. A friend told us we have to check out the Afton Fair.
Bring a cooler for stopping at Wegman's in Binghamton or Scranton on your way home! Pick up a bag of salt potatoes (an upstate thing), and if you make it to Skaneateles, get some Wake Robin Farm Yogurt at the Skaneateles Bakery.
I hope this is helpful, and if I think of more ideas, I'll post them!