There are lots of things to see in all of those states, and lots of hotels/motels/ B&Bs.

BTW, $80/day for a rental car seems really high.

I should also have added that we will have to fly back to Chicago. Is it best to return the rental car in Boston and fly back from there or to drop the rental off at an airport in another state. I have 0 experience in regards to renting a car in another state.

I also want to do Salem, so I suppose we would flip-flop the days since Salem is driving North.

abram, I am glad to hear that you think that is high. I believe I got that price through Enterprise and picking the car up in Boston. That's the price for an economy car. I went back and put in different information (pick up at Logan International and drop off in Providence, RI) and came up with $47/day for economy cars which seems more reasonable.

..."Vermont, New Hampshire, Maine on Friday/Saturday..." - is there enough to see along the drive, the coast etc to make the trip worthwhile?"

Yes.

Heck, there's enough to see along the coast of Maine alone for a two-week trip.

Also, there are hotels everywhere except the deep interior of Maine.

Be sure you can rent a car. I thought most rental companies won't rent to under 25 year olds or, if they do, will tack on a big surcharge.

Take the Amtrak Downeaster from Boston North Station to one of 3 New Hampshire stations. Take the next Downeaster to Portland Maine. There are 5 trains each way everyday. http://www.amtrak.com/servlet/ContentServer?c=AM_Route_C&pagename=am%2FLayout&cid=1241245668499

Take the Northeastern Regional from Boston South stopping in Rhode Island and catching the next train to Connecticut.
You will have to go into New York (Penn Station to get on the Vermonter.
I got off the Empire Builder and took a picture of the station sign in Williston North Dakota since I was not sure that I had been in North Dakota before. I'm hoping to get to Alaska and Hawaii sometime in the next 2 years for all 50.

Make sure you don't rent your car until you are ready to leave Boston, the T is easier and much cheaper than going in a car. You can also get to Salem from Boston on a short train trip if you want and the walk from the station to the center of the historic area is only about 10 minutes or so.

You could easily do Rhode Island and Connecticut in a day if you didn't want to spend too long in either place. Perhaps a stop in Newport, RI for a look at the mansions and Mystic Seaport in CT.

From Mystic head west on I 95 for about 15 miles to CT 85 north to I 395 north which turns into 290 in MA and then up to 495 from which you could head north to NH then do a zig west to VT then zag east to Maine before heading back to Boston.

There are lots of places to stop in all these areas.

The first week of October has good and bad points. For all except the mountains you are probably too early for much fall color - but that will make it esier to find a place to stay. If you wait a week or so - and hit the best of the color near boston the views will be better - but hotels probably alot harder to find.

The area you're talking about could easily take a month. I think you should decide what yu really want to see and do. if you just want to set a foot in - you can get from Boston to NH in well under an hour and not much more to get to the top if Maine. Than you could head south to actually see something briefly - Newport and Mystic are fine. Vermont is an outlier - and would take some time.

Exactly how many days do you have?

Have you checked on cost of car for someone your age (and if you want 2 drivers that's extra) as well as drop off at another airport. Not sure of the flights from Chicago - I would start there,

Gbelle: We are old enough to rent a car, hence the "something," but good catch thanks!

Tomfuller: never even thought to train it! We took amtrak from Chicago to DC and loved it. I suppose that would take a bit more planning though, specifically knowing what days we want to be there. I suppose we thought of renting a car for a bit more freedom but we will definitely look into it!

Emalloy: taking a train to Salem might be a good idea, I assumed it would at least have some sort of tourist following being so close to Boston. Would you then suggest taking the train back to Boston and picking up a car there?

NYTraveler: We did DC the first week of October this year and hit what I assume to be unseasonably warm weather with it being in the 70s. The reason we chose October was because I don't handle heat very well. I prefer to travel in the 60s or so. I had no idea that a week or two difference would change the availability so much. I assumed since it was out of September it wasn't considered tourist season anymore as I am used to "touristy" vacations/spots. I had no idea having 2 drivers on a rental car would also cost extra. That seems odd. We were looking to fly into the area on Saturday and can stay as long as the following Sunday or about 7 days of sightseeing.

Thank you all for your input. It really gives me many things to think about!

For car rental, check where you get the best deal and consider the cost of travel to or from the drop off/pick up point. I'm not sure Salem is large enough to have much in the way of rental car facilities, but it might. If you did it as a day trip from Boston then you wouldn't have to worry about what to do with luggage etc..

If you don't care about foliage colors, you might switch to the last week in Sept. We usually do a third weekend of Sept getaway and usually have great weather but, yes, it could be warm during the day. First week of October is one of the biggest tourist weeks of the year and you will see tour buses along the popular routes. You might also find 2 night minimums at some hotels.

If you are history buffs, you might consider Newport RI for the mansions, native American museum at Foxwoods casino in CT, Mystic Seaport in CT. If you don't mind the mileage, maybe Shelburne Museum in VT with an overnight in Burlington VT (college town on Lake Champlain), drive over to NH with a stop at one of the grand hotels and maybe Castle in the Clouds that overlooks Lake Winnipesaukee. Next day tour Canterbury Shaker Village (check open hours since it's Sept/Oct). Drive over to Portsmouth NH's Strawbery Banke Historic Area, drive across the bridge to Maine so you can say you've been there. Back to Boston. You can do a boat tour of Portsmouth's harbor but you can also see the closed up Navy Prison from the road (Rt 1B) and wonder what they will ever do with the building.

Dfrostnh-What great suggestions! I can't wait to start looking up some of these places!

EMalloy-probably the right idea seeing as we don't want to have to lug our luggage everywhere!

The Comunbus Day weekend is one of the busiest of the year in New England due to leaf peepers. Hotels are often booked out months in advance - since this is prime time.

And for first week of Oct 70s is not very hot for DC - although it is usually cooler in New England. October weather can be Indian summer (80s - or 60s with cooler at night).

and yes, you need to notify the agency how many and who the driver will be. If an unappproved driver is at the wheel when there is an incident of any sort the insurance is invalid - and you would have to cover all costs out of your own pocket. Expect there to be a regular daily charge for the second driver.

Driving in Boston simply put...sucks....we live two hours north in Central NH and we love to visit Boston but absolutely dread the drive. We park our car for the duration of our visit. We also live 90 minutes from Portsmouth, NH and love it as a destination. The "downtown" is always lively, even on a Sunday night. It's close to UNH (Univ. Of NH) and thus the town has a lot to offer younger crowds. Our absolute favorite place to eat there is the Portsmouth Brewery...great food, awesome beer, always busy. Expect a wait during peak times. I also recommend Kennebunkport, Maine....summer home to the Bush family (yes the presidents). While there I recommend Federal Jacks (another brew pub with great food and beer...notice a theme here?). In CT I recommend Mystic Seaport. All of these locations are along the eastern seacoast.

definitely stop at the Mystic Seaport!!! and a walk around Yale in New Haven is also nice. Make sure to have pizza at Modern Apizza on State Street.

Last year we found that with a Costco membership, many rental car agencies will drop the extra driver fee plus give you a Costco discount. Even with the Costco membership fee, we saved money. Also, we have found some good car discounts on rentalcarmomma.com.

With some rental agencies if both drivers are AAA members the 2nd driver fee is waived. It might also be state-specific but it's something you should look into to save some money.