Certainly a road trip in New England is worth it, regardless of time of year. I just wouldn't plan on foliage, except maybe in the farthest area of northern New England and even then only by the end of your trip. Really, I think you should just plan a New England trip, and not call it a foliage trip. That would be setting yourself up for disappointment.

I would start on Cape Cod, because it would be quite lovely in early September. Should even still be beach weather.

I recommend booking hotels for your weekends. You may be able to play it by ear during the week, but it can be way more frustrating weekends. I would also book hotels for whatever time you are planning to spend in Boston itself, if any.

Thank you for replying.....I am currently looking at the hotel situation as we speak. I definitely would like to spend one night in Cape Cod and Nantucket. Any recommended restaurants in those areas or Boston? Are there any good websites or phone apps I can use to find these while I'm traveling?

Unless you want to spend all your time in the car you will want to narrow the places you plan to visit.
When foliage happens and how vibrant it is depends on temperature and rainfall. If the drought continues the foliage will not be very vibrant. But it is still a beautiful place to visit at that time of year. Enjoy.

Chowhound.com is a great website for finding restaurant suggestions. You can either search on the name of a town or post your own question. Go to the southern New England and Greater Boston threads.

Consider the travel time to get to Nantucket assuming you go by ferry. Perhaps you need more than one night. We did a weekend on Cape Cod 2 years ago and did a day trip to MV. That was nice but not long enough.

The only color you will probably see is the red of swamp maples in some low lying swampy areas and the occasional tree that for some reason colors early.

But to ask if the region is worth seeing if there's no color is silly. New England is one of the best areas in the country for doing lots of things. King Richard's Faire in Carver (near the Cape), food tours of Boston or Portland Maine, boat trips to islands, kayaking, zip lining, etc. Depends on your interests. You'll find plenty to do. Wine, cheese or ice cream trails? Great Vermont Corn Maze in Danville (northern VT near Lancaster NH just above the White Mountains. There's even a thread on Northern New England/chowhound about destination restaurants.

Haven't been to Simon Pierce since the big flood, Quechee VT. It's fun to find places like the Humble Kitchen food truck in Brattleboro VT for bahn mi sandwiches. If you like Chinese food, highly recommend the food tour of Boston's Chinatown which ends with lunch at a dim sum restaurant. Wonderful lobster shacks in Maine will be open weekends in Sept but check for hours.

Keep in mind that we like to spend at least a half week in an area doing road trips and staying at the same place. Given the time of year, you might think about staying on the Cape for several days depending on how much you like beaches.

The weather in September will be very nice, although no foliage. You will still have a great visit here. Route 93 is the main highway from Boston all the way into northern NH.

Do you have any particular interests? That will help in giving suggestions too.

Last year we took a trip up to about as far north as you can go in Vermont at the very end of September. The foliage even up that far wasn't nearly as "complete" as one might hope but it was still a worthwhile trip despite many washed out roads from the hurricane/storm.

I agree that not counting on seeing a lot of brilliant foliage at that time of year is a good idea to avoid disappointment.

At this point, we are more excited to see it and experience the great food and culture. I have wanted to do this for years and I am definitely not questioning whether we should come out there or not instead questioning whether we do the road trip or pick a few different destinations in the region.

We are foodies....and we love to be active, attend local events, etc.

September may be the best month of the year to visit northern New England - the weather is still warm, the summer crowds are gone, the foliage crowds haven't started yet, and most of the blackflies and mosquitoes have quieted down. There are many great place to eat on the Cape and along the Maine coast. Needless to say, they are predominantly seafood, but there are also great Asian, Italian, etc places to be found. Rural New Hampshire and Vermont are extremely beautiful, but not really meccas for interesting dining. The exceptions would include Burlington Vt, Brattleboro Vt, Woodstock Vt, Hanover/Lebanon NH, North Conway NH. If you really want great dining, drive up to Montreal for a night - a foodie's paradise.

We were thinking of going to Nantucket and Martha's Vineyard. How long of a stay is recommended to see and experience each island? Is one island recommended over the other? How long is the ferry? Any restaurants suggestions on these islands? Any other suggestions of things to do? Places to see?

Check the ferry schedule. We have only gone to MV, chose the departure time that was convenient which turned out to be the ferry to Oak Bluffs. On the way over, we made arrangements for a private van tour but could have used the bus system. You will have to park at one of the ferry lots which has a bus to take you to the dock. It's a short ride but time must be allowed to do this and buy tickets.

It was only one day for us and not nearly enough time.

For Nantucket and Martha's Vineyard, I'd recommend a minimum of a day each, and two days each wouldn't be at all unreasonable.

One day on Cape Cod would just scratch the surface. There are several enjoyable towns to visit (Provincetown, Chatham, Wellfleet, Falmouth, Sandwich), beaches galore (especially the Cape Cod National Seashore along the eastern edge of the Outer Cape), several attractions, and the drive along Route 6A.

For food suggestions, agree that Chowhound is a great place to get such advice. There are some very good threads here as well on Boston and Cape Cod eateries, which a board search will turn up.

Doing both islands on one trip might be overkill. MV is bigger, and closer to the mainland. Nantucket is more remote, more expensive, and less crowded. Either one is great however. As the above mentioned, Cape Cod is quite scenic itself, with scores of beaches, lots of back roads, and plenty to explore. There are many, many good restaurants on the Cape.