I recommend that you get a guidebook about Boston and both read it to select what you want to see. Then plot those points on a map so you can group them geographically.

The destination section opf this website is another good resource; their sample itineraries might be helpful.

Stay as close to the center of the city as possible perhaps?

Where are you coming from and what's your total budget?

My mother was a historian AND I'm from Lexington, so maybe I can help you out! LOL.

Keep in mind that October is the best, and most popular time for visiting New England. Boston hotel prices will be high. And you should probably plan to make reservations in advance. Since leaf peeping will be going on, you may run into minimum stay requirements in other parts of New England (though this is less the case if you go mid-week).

If you can swing a hotel downtown, then you should definitely do so. And you have it right...mass transit while you are in Boston, then get a car when its time to leave. Its not too bad to pick up the car from a downtown rental agency and the get out of the city.

You can fill up as much time in Boston itself as you care to spend. Definitely take a look at the Fodor's destinations/itineraries to get an idea of what things you want to see, and that will help you decide how long to spend. I'd guess around 3 days, but maybe more if there is more you want to do.

You can do some outlying areas easily as day trips if you prefer: Lexington and Concord, Rockport, and Salem are some of the most popular.

After that you have tons of choices...Portsmouth New Hamshire, Portland Maine, the White Mountains in New Hampshire, Vermont around Burlington and Lake Champlain, Newport RI, the Berkshires....thats just a smattering. If you want to see foliage, then recommendations will really depend a bit on exact dates. earlier in October you should go further north. By mid October, southern New Hampshire and most of Massachusetts will be getting to peak. Do a search on this forum for New England or foliage or leaf peeping trips, and you will see lots of ideas for itineraries and places to go.

Are you flying or driving?

There have been tons of recent posts on this topic if you can use the search function.

china_cat's advice is excellent with two exceptions: don't go to Salem after October 15 (Halloween foolishness) or plan to be in Boston the weekend of the Head of the Charles Regatta, October 20-21.

Priceline is good for Boston hotels but be careful where you are bidding. The closer to the center, the better. In general you can get to the places you and others mention by T (subway and trolley) or commuter rail. There is a terrific fast ferry to Salem but it may quit around Columbus Day.

Lodging is expensive in Boston and food might be, but there are fantastic inexpensive options we can help you with when you are more certain where you will be.

<<<or plan to be in Boston the weekend of the Head of the Charles Regatta, October 20-21.>>>

Unless you want to see the Regatta, of course Didn't someone on Fodor's go last year and post that it worked out well, including good views. Maybe that wasn't the Head of the Charles?

The regatta itself is fabulous if it is not bucketing down rain and blowing a gale. It is best watched, I think, on Mmeorial Drive near Weeks Bridge across from the B School. You don't have a clue who won, of course, but the views of the passing boats is terrific.

No, my issue is crowded hotels and restaurants and large numbers of very large young people wandering around everywhere. Traffic is seriously disrupted, and the T is packed. But a wonderful good time.

http://www.newburyguesthouse.com/directions/index.cfm

this is a centrally located guest house which is reasonably priced. you can walk or take public transportation to most of the city from here. Parking is free if you have a car.
I recommend the Gardner Museum, Boston Fine Arts, an orientation tour of the city, the Freedom Trail and the Fanueil Hall area as a start to your visit. Day trips to Lexington, etc are very nice and October is the perfect time to see it.

Boston for a few days and then drive to Acadia National Park. Stay in Bar Harbor while visiting the park for 2-3 days.

Since you're still thinking about this trip, beware that you'll have major hotel sticker shock if you visit Boston in October. Unless you really want to see fall foliage, pushing your trip to November may save you a bit of money on lodging.

Concord and Lexington is an easy drive out of the city. Although you can possibly visit them via commuter rail, it's not that convenient without a car. OTOH, towns like Salem is totally doable by commuter rail, and (I think?) Gloucester.

<<<Although you can possibly visit them via commuter rail, it's not that convenient without a car.>>>

Out of curiosity, how would you get from site to site within Concord, for example, without a car? (ex. from the battlefield to Louisa May Alcott's home to Walden Pond, and even to downtown Concord)?

on horseback or a days march like the minutemen?

A car is worse the useless in Boston - stay in the center and you can walk to a huge number of sights or grab public transit to anything too far.

You can get to NYC easily vie either Amtrak (buy tickets in advance to get a discount) or vis one of hte reliable (not china town buses).

Since this is a very busy time of year I would start looking for hotels now and see if you can get a prepay discount. (SOrry I can;t give specifics - had family there that I stayed with on most trips - so my only hotel experiences are congresses - one of the hotels attached to the convention center - and they often don;t have deals.)

sf, if one is ambitious, one can possibly walk from one site to another. Concord itself isn't that large.

But during tourist season, there is a trolley tour bus that has loops around the main sites: http://www.libertyride.us/libertyride.html

Both food tours of Boston, the North End (Italian) and Chinatown, include fascinating history as well as wonderful food samples. You can fly in and not need a car at all unless you are going to visit other places. The JFK Library is also very interesting as well as all the Freedom Trail stops.

One way to get to and around Concord and Lexington without a car is on a bicycle.

The wonderful Minuteman Bikeway goes from Alewife station in Cambridge to Lexington and eventually to Bedford. It's about a 7-mile trip on the Bikeway from Alewife to Lexington and the Battle Green, and then a mile or so more up Mass Ave to the Minute Man National Historical Park. At the latter, there's a wonderful pedestrian and bike trail, the Battle Road Trail. From there, you could work your way into Concord Center and to Bedford, where you'd catch the Minuteman Trail back to Alewife.

That route is roughly 25 miles, with a very gentle uphill from Alewife to Concord. If you can get yourself to Bedford (there's a MBTA bus), you can rent a bicycle at The Bikeway Source (a shop at the Bedford end of the bikeway), then pop over to Concord and Lexington.

With the exception of Walden Pond (which is a good bit further out of the way), it's entirely possible to walk between Concord MA tourist sites and the commuter rail station. Being a hearty walker like me helps, but it's not in my experience out of the question to reasonably see all but Walden Pond on foot from the station. Of course, if a seasonal trolley exists, I say take full advantage.

Lexington is not reached via commuter rail, though last I knew it was easy enough to take a local bus (weekdays only, though) between the Alewife subway stop (last stop on the Red Line in that direction) and the attractions there.

The Minuteman Bike Trail is a very good idea as well for visiting Lexington (it goes right through the center of town), if you're a cyclist. You'll need to go beyond the end of the bike trail (it stops in Bedford) to visit Concord via bike, but I've seen people do so.

Depending on interests, I'd think a minimum of three days for Boston/Cambridge is good, and more wouldn't be unreasonable. Definitely take a look at some good guidebooks and search posts here.

Should also add that if the plan is to spend 10 days in Boston, you'll be able to see most everything Boston/Cambridge have to offer as well as take several of the sizable number of excellent day trip options available from there: in Massachusetts alone you can consider Plymouth, Salem, Lexington, Concord, New Bedford, Marblehead, Gloucester, Rockport, Lowell, Essex/Ipswich, or the fast ferry to Provincetown. Or as was suggested, you could spend a couple days exploring areas beyond simple day-trip realms, like The Berkshires, Pioneer Valley (with or without Old Sturbridge Village or Worcester), Cape Cod and the Islands, or places in neighboring states.

If you like pizza, go to Pizzeria Regina's in the North End, fabulous but be prepared for a line, especially on weekends. Well worth it, and you can make new friends. They've been around for about 100 years-seriously.

Rick

Regina's is great - be sure to go to the original rather than outposts such as Faneuil Hall ( where we were served slices that weren't hot)

Finally had a chance to get back here!

Hubby wants to fly into NYC (we were there 3.5 days in April), stay 4-5 days, then take amtrak to Boston, similarly to how we got to NYC from DC in April. Leaving Fresno on a Tuesday, October 2 or 9, returning on a Thursday, October 11 or 18. He's vetoed going to New England this trip. Living near Yosemite, we've seen mountainsides full of color, so that's okay.

As I posted, we like walking around but not marathoners. And we're not hikers. We raced around DC and NYC, but hope to take things slower this time.

Since we saw a lot of our "must see's" in NYC in our crazy race, we can take things slower in general and enjoy more. Catch things we missed and repeat where we wanted to spend more time. Funny, when talking with Hubby, the things he mentioned were all FOOD! We're familiar enough to figure out what else we want to see--the NY Public Library in more depth, that museum on the Lower East Side (can't remember the name), St John the Divine, maybe the High Line and a play or musical, and spend at least half a day in Central Park if the weather's good.

As for Boston, we're looking at the Freedom Trail, walking around Harvard and MIT, Fenway Park. Things like that. By not leaving the immediate area, we figure we can take it slower, since Boston's doesn't look huge and there's a good chance this will be our only visit. The "T" looks like great transportation, so I don't think we'll need a car. I grew up in the LA area, where a car is needed because everything you want to see is at least 20 from everything else you want to see.

I guess what I'm seeking is help on places to stay in Boston...In the city? In Cambridge? Elsewhere? Any specific deals on hotels? We're hoping for $200 or less (much less?) a night.

Early/mid October is HIGH season in Boston - between the leaf-peepers and parents of students here for parents' weekends, it'll be impossible to find anything <$200. You will NOT find any deal for that time period. I suggest you start looking for a place to stay right away. Some Fodorites have had good luck with John Jeffries Guest House.

I'd choose staying in Boston proper over Cambridge, but if you can find something affordable in Cambridge, then by all means book it!

Many years ago I went to a wedding somewhere SE of Boston.
We stayed in a hotel near Braintree and got a ride to the T station to go into the city of Boston. http://www.mbta.com/schedules_and_maps/rail/
As I recall the nice hotel was somewhat cheaper than staying in the city. We enjoyed the Science Museum which had Van DeGraff generators built by VanDeGraff himself. A man standing in a steel cage talks to you while lightning hits the cage.

I think tomfuller may be talking about the Sheraton in Braintree. No atmosphere, busy commercial area, but generally good prices.

The Hilton in Dedham is within walking distance of a commuter rail station. This isn't as convenient as the T, but their prices have been consistently much cheaper than city hotels and are often available on Priceline.

Both of the **** hotels at Logan are not terrible places to be for touring, but I would not bid on any of the *** on Priceline because of location issues.

There is a reasonably priced guest house on Newbury Street...it may even be called the Newbury Street Guest House or inn. You really do need to book soon.
If you do decide to rent a car for an excursion I second the recommendation for Portsmouth NH ( about an hr north) you would not be disappointed.

Now, after all this great info, things don't look so good. Hubby's job is going a bit strange. Not a threat of losing it, but he's frustrated. Very toxic place. He's trying to transfer. In the meantime, a friend living in Hawaii until the end of the year invited us to stay with her for a vacation. We might have to do that (yes, HAVE) for the bargain, to see our friend, and because Hubby needs a break before he breaks.

Well, I don't know how far it is for you to go to Hawaii, but I will say, if you need a break, Hawaii is the place to do it! Hope things get better.

We're in Fresno, CA. Any flight would transfer from LAX or SFO, but that's fine.

Our Friend is in a 2bd/2ba place, with parking for 2d car and car rental 2 bulks away! How perfect can you get. I just need to wear long sleeves or use high level sunblock. I went to Hawaii 26 years ago with my parents and did not use a high enough sunblock. Severe 2d degree burns from shoulder to shoulder across the top 3" (skin exposed when standing in water), leading to ER visit. So laying in the sun is not for me; laying in the shade is just fine.

Friend suggests a 3-4 day tour of the other islands, so I'm looking into that. We could have as much as 11 day. Hubby wants to see Oearl Harbor/Arizona Memorial.

All dependent on Hubby actually being able to get the time off. Assuming he does, are there things/places that advanced reservations are really required?

you should definitely start a new topic, and tag it hawaii. Otherwise you will not get the right people looking to help you out.

It sounds like a great idea though..Hawaii is the place for a real break