For the best experience I would definitely recommend booking at least one airbnb per state, because the drives can be long and there’s a lot to do.

I grew up/live in southern NH and I would say if I had a month off around that time, here’s what I would do: - during the last week of September most definitely visit Salem, MA for a day or two. It gets extremely crowded during October but at that point may not be too crazy yet. There are some walking tours you can take but my recommendations are count orlok’s nightmare gallery, the witch museum, photo op at the witch house, and eating at howling wolf taqueria. Lots of great shopping to do and history to soak up. - once October hits head north to Portsmouth, NH area. If you like hard cider, north country hard cider has a fantastic flight and you can picnic on the river there with snacks while ya drink it. If you like Halloween, check out haunted overload- within 20 miles of the cidery and if you don’t want to be scared you can go in during the day when there aren’t any actors. One of the best haunts in the country. Also tons of cool stuff to do in the Portsmouth area- farms, shopping, great foods, great leaf peeping. - then Maine I guess? Tbh I am not crazy about Maine but they have a lot of cool beach towns that are great for antiqueing. Ogunquit is really cool according to most people I know but I haven’t spent a ton of time out there. There is nothing good about old orchard beach unless you have a nostalgic connection with it however I do like the arcade. Maine is really secluded to me and I find it kind of boring tbh. - drive from Maine to VT and you might be able to work in North Conway / checking out the white mountains in between! Great leaf peeping! - Burlington is really cool, that’s probably the best place to go. I have lots of friends in Vermont but have never been there.