New England/NY in early fall
 

sorry if you've covered a lot of this before but...
road trip starting Boston early September (Labour day) finishing with about five days in NYC. Itinerary suggestions please and also advice on weather/clothing and if it's necessary to book for the whole time (flying to NYC on 19th).

September is still really summer. Days will be warm (usually 70s/80s) but nights will usually be cooler than in the summer so be sure to have a light jacket or sweater.

Definitely have hotel reservations for Boston and NYC (neihter will be cheap).

As for the road trip - I'm not clear on your dates, how many days you have, or what your interests are. Do you want hiking/outdoor activities? Antiquing? Touring famous houses? Just looking at scenery?

You really need to provide more info.

Thanks Nytraveler. Dates: New England 5th -19th Sept. NY 19th-24th September. Interests: 'pottering' (probably a very English word!) ie seeing what the locals recommend, so all your suggestions but probably not into hiking that far.

Some locals will be going to country fairs on weekends. Expect heavy traffic on Sept 5 Labor Day southbound toward Boston from points north. You'll probably be heading north but keep in mind some day trippers will also be heading north in the morning.

Weather is usually beautiful unless a hurricane is expected. Unusual but possible. Agree that light jacket will be needed at night.

If you like music, people and lots of things going on, head toward cities like Portsmouth NH and Portland ME. Take a boat trip. Both Portsmouth and Portland have them.

Although hiking isn't my favorite activity, the hike thru NH's Flume in the White Mountains is very pretty and worth it but it's very popular so go mid-week.

Each New England state has maps usually put out by the Dept of Agriculture to find breweries, wineries, and ice cream stands. I know Vermont has a "Cheese trail".

Visit a farmers market, generally on Saturdays. Vermont has some excellent ones where you'll be able to get lunch and snacks.

It really depends on your interests. I prefer art museums. My husband prefers classic car museums. If you go to Rockland ME area you can visit both plus a winery and a great lobster shack. Pay attention to schedules. Some lobster shacks will be open weekends only after Labor Day because the summer help goes back to school. There are still plenty of restaurants but lobster shacks can have better views and cheaper prices.

There are also some apple orchards that grow a wonderful variety of heirloom apples.

In NH there is a free weekly newspaper about events and happenings and also has a website: Hippo Press.

County fairs all tend to be July & August, not in September, but aside from that I agree with what dfrostnh has written.

It's usually a great time to visit as kids will be back in school and the weather will still be warm & (hopefully dry).

Even if daytime high temps are in the 70's You should be prepared for cooler nighttime temps - a light jacket & long sleeves will be enough.

For the big cities you will want to book rooms ahead, but for the rest of your trip I think you will be fine being more flexible on dates without any major issues.