With only 5 days, consider flying into Portland, Maine or Manchester, NH if you want to visit Northern NE. For Southern NE, consider flying into Providence, RI. You'll save a few hours of driving and lots of headaches.

What is the goal of your trip? Do you want to see coastal NE, or do you want to see fall foliage? Foliage tends to be more intense inland in the mountains and less so along the coast.

Mid-Oct is peak foliage season in NE, so you may not be able to stay at cute B&Bs as those are likely fully booked. OTOH, coastal Maine is less popular than inland NH/VT, so you may be able to find decent logding.

Mid Oct is the start of low season up the coast, with most of the lobster shacks etc closing after Columbus Day. You should feel comfortable just winging it with a B&B guidebook in hand. Towns to search here on the fodors forum for previous trip reports etc include Rockport MA, Portsmouth NH, Ogunquit Me, Kennebunkport Me or Cape Porpoise, Camden Me, Boothbay Harbor.
Note that "coastal route 1" does not hug the coast like it does in California and is not particularly scenic for the most part. Most of your destinations will branch out a few miles from the coastal route.
I would think you'd need to keep a sharp eye on the weather and possibly change plans if the Maine coast is cool and windy, or rainy. Heading south and exploring Cape Cod would be an idea, not crowded at this time of year but might be a little warmer than Maine. Maybe combine a 3 night trip to the Cape with a couple of nights in NEwport RI?

From Denver, it's possible to get nonstop flights into Boston while Portland or Manchester involve connections. So, depending on your final choice of destinations, Boston could save you some time in the long run. Because of the 2 hour time gain, a return flight from Boston at 8pm will get you back to Denver at 10:30pm and afford you some extra time to explore on that final day. Boston traffic wll be heavy at 6pm however so plan accordingly, maybe exploring the coast near Boston on that final afternoon/early evening

Agree with yk. If you really want coast, don't expect much foliage and it's really true that the "coastal route", Rt. 1 isn't on the coast for the most part. You have to go down dead end peninsulas to get to the ocean. Having said that, off season can be delightful along the NE coast, less crowded, going without reservations is possible but some places are closed and weather could range from lovely to cold and rainy. Let us know a little more about what you're looking for and we may be able to offer more help.

Thanks for all the info! Being from SoCal I had no idea the beach towns shut down in fall/winter or that Rt 1 was not coastal like the Pacific Coast Hwy (which I grew up on). The reason for flying into Boston is that we have Frontier flight passes and that is as far North as we can get on Frontier. I want the fall foliage, so inland it is. I'm completely open to suggestions for a 5 day trip out of Boston...so which direction would be best? Massachusetts, Connecticut, New Hampshire, Vermont? I want to see it all..but maybe not all in one trip. Thanks!

One option would be drive west from Boston along Rt 2 (the Mohawk Trail) out to Western MA/Berkshires. Spend 1-2 days there. Then head north to VT and then east over to NH, and loop south back to Boston. Can't help with VT/NH routes but there are many more knowledgeable posters who hopefully will pitch in.
http://www.massvacation.com/rtc/mohawk.php

I would not suggest doing Rt 2 west from Boston. Between Boston and Greenfield it's a rather boring drive - not un-pretty but not a 'destination' drive. No quaint towns or anything. It's a highway. Between Boston and Charlemont is more interesting but still not that great. And Rt 2 west of Charlemont is closed due to damage from Hurricane Irene and will not re-open for several more months.

If you want Massachusetts I would take the Mass Pike (boring, but faster). Sturbridge Village is a living history museum that is worthwhile. It's very pretty in the fall, plus there is lots other to see besides leaves. Then continue on the Pike to the Stockbridge/Lee area. Or if you want to head north then get on I-91 and stop in Northampton and Deerfield as you head to Vermont. Then you could do a little of Vermont and loop back through NH back to Boston.

HOWEVER - unless things change drastically in the next week this is going to be the worst year for fall foliage in decades. Seriously, there is hardly any color and the leaves are just turning a lame yellow/brown and falling off.

New England is still one of most beautiful parts of the country, but if you are coming here for the fall foliage this year I suggest you make sure there is something else you want to see besides leaves! I really think the coast would be your best bet this year. Not as color dependent as western New England for pretty scenery. There ARE trees on the coast, just not vast hillsides of them. And this year the vast hillsides are going to be kind of disappointing. The gorgeous, rocky, New England Coast will still be gorgeous.

With five days in mid-Oct I would go up the coast as far as Camden Maine and then work my way down: Boothbay, Portland, Kennebunkport, Ogunquit, York. Then spend the last couple days on Cape Ann (the 'North Shore' of Boston) - Gloucester, Rockport, Hammond Castle, Salem. Have you been to Boston itself? Definitely worth a couple days there. But now that's more than five days.

I am in eastern/central MA & unfortunately, I have to agree with Isabel that right now there is very little fall foliage. The leaves are either still green or brown/dull yellow. I don't know what it's like up north or in Western MA.

So I'm inclined to suggest a coastal route as well, either north of Boston as far as Maine. If you have the time, Acadia NP & the Schoodic Peninsula has spectacular rocky coastline. Or the Cape is beautiful this time of year & would be warmer as someone else suggested. The Cape Cod National Seashore is beautiful & I recommend staying in towns such as Eastham, Wellfleet, Truro or Provincetown. Wellfleet hosts the Oyster festival in mid-October. Chatham is also a nice place to stay.

If you want to chance the mountains looking for foliage, I think the Berkshires in western MA would be a great choice. It is beautiful & if there isn't any great foliage or you have rainy weather, there are some wonderful museums, such as Norman Rockwell Museum, Berkshire Museum, Clark Art Insitute, to name a few. And you could also spend a few days in southern Vermont, too.

Thank you all for the help. After much thought thinking of staying near Boston and a couple nights somewhere near Cape Cod, any suggestions?

ArDelucc, Since you have decided to do Boston and Cape Cod, consider not getting a car until you leave Boston. The public transportation is good, so get lodging that is an easy walk to the T, you will save both rental costs and parking fees as well as the headache of finding parking, and dealing with the unique rules for driving in Boston. If you want a sea adventure, take the ferry from Boston to Provincetown and get a car there.

You don't want to be "near Cape Cod", you want to be on Cape Cod. My preference is somewhere from Eastham to Ptown.

Color is just starting in southern New England, but much more muted due to the beating hurricane Irene gave the trees.

Have a great trip.

Thank you so much for this information emalloy..it is very much appreciated!

ArDelucc...a boost for my hometown, Quincy. If you are staying in Boston or heading south to the Cape, a short ride off the interstate will take you to Quincy....the birthplaces of John and John Quincy Adams. The Adams Mansion on Adams Street is a great piece of colonial Americana. A few miles south, the two Adams houses in West Quincy are well preserved and make for an interesting visit. The Thomas Crane Public Library is a magnificent piece of unusual 19th century architecture. Across Washington Street is the First Parish Church, the resting place for John, John Quincy and their wives.

There, I've done my job as a transplanted Quincy-ite (L.A.), after being away for the last 54 years (I do get back for visits). By the way, it's pronounced "KwinZee" ... From there it's a pleasant quick ride to the cape, with Plimouth (Plymouth)Plantation, a replica of the Mayflower and Plymouth Rock can be visited.

stu tower, a son of Quincy.

dunno if this is still true, but at one time, Orleans was one of the nicer towns to visit on the Cape...many visitors go all the way to P-town, too. At any rate, the summer hordes will be gone by the time you visit.
stu

Orleans is a good centrally located spot to base oneself on the Eastern part of Cape Cod, especially if you want to forgo a car. However, I'd choose Wellfleet if you prefer more charm, or Chatham if you want a full and somewhat upscale feel to your home base town. And Provincetown is indeed excellent to visit.

Up along the coast might be best or to the charming Cape. I was wondering about foliage this year and several have mentioned problems. Of course the Berkshires are worth visiting with lots of art and also Old Sturbridge Village en route. Thanks to yk for info on the Mohawk Trail.

Since (and before) moving to this area we've done some exploring. I like Old Strawberry Banks in Portsmouth, NH.
Also we've been to Maine on several occasions. Of course you might explore historic Boston area, including Lexington and Concord areas.
www.fodors.com/community/united-states/maine-minitrip.cfm

www.fodors.com/community/united-states/history-in-concord-mass.cfm

Bill in Boston

There are so many beautiful Cape towns to enjoy. If you don't want to venture too far onto Cape Cod from Boston you will enjoy a stay in Falmouth or Sandwich. Both are charming and typical New England, Cape towns. The ferries to Nantucket and Martha's Vineyard are nearby too.

If you continue to the outer and lower Cape areas you can consider staying at one of the many inns in Chatham, also one of the most charming towns I've ever seen.

Orleans is conveniently situated near Nauset Beach and enjoys a year-round population.

Fort Hill in Eastham is the only b&b directly in the National Seashore confines and they get great reviews. They have a cottage that is separate from the main house that would offer you privacy but availability might be limited.

The towns between Eastham and Provincetown offer the opportunity to really get a feel for the rural atmosphere of the Cape and gets you out of the Cape 'suburbs'. Provincetown has some of the best restaurants on Cape Cod. Make sure you make a visit to the beaches of Wellfleet, Truro, and Provincetown. They're stunning.

This is definitely 'off season' on Cape Cod (a favorite of many, including me) so the atmosphere is quite different than during the busy summer. You will find some places to be closed for the season but there are plenty of choices available to enjoy year round.

The hurricane blew so much salt water into the air on the Cape the chlorophyll was affected and things are largely painted with a brown brush this year. But the beige beach and blue water looks summerlike! Conversely, my little town in central Connecticut is bursting with reds, oranges, and golds!

I love Cape Cod in October, but wanted to mention that it doesn't have rocky coast like you'll find in Maine, and to some extent to the north of Boston in Cape Ann. Just wanted to make you sure you were aware of this since you said you hadn't been to the area before.

ArDelucc:

ArDelucc:
Sorry about the hiccup. PCH is a long series of hills winding up and down the coast with views across the water to the horizon. New England is much less long vistas and is in fact a series of snapshots of rocks and beaches. I'm not saying this well, but there is no comparison. Connecticut, Rhode Island, Massachusetts and Maine are different and special.There is no equivalent to the PCH. The only things linking them is the water and the fishing villages. It's kinda like the villages around the Straight of Juan de Fuca in Washington State. The cape is a series/grouping of small fishing villages. Lots of old houses with widow's walks. The beaches are super in season but frankly there is not much going on out of season. Many of the best restaurants are closed for the season. There is some whale watching but I'm not sure about the seasonality of that. Inland Maine, Vermont and New Hampshire have more of those quaint old New England homes. There are mountains (you might call them hills)and trees, valleys and more little villages. It may sound boring but each area has its charm. Like Amherst Mass.a little college town, Portsmouth N.H an old seafaring town, Manchester Vermont a resort town for longer than anyone alive can remember. However, in its early days it was almost exclusively for the rich and famous, still evidenced by Hildene, the summer home of Robert Todd Lincoln, the son of the President. As I said before each is special and one of a kind . I don't know if I've helped but I got the sense you were expecting PCH with covered bridges, and country churches. It's not. Having said all that I spend a couple of weeks each year around October in New Hampshire or Vermont. It is lovely and very relaxing. Finally whatever you decide do you research it will make the difference. Enjoy!

just to clarify: Actually, only a few of the best restaurants have closed for the season on Cape Cod and the abundant restaurants that remain are as wonderful as they were this summer. I never think of Cape Cod as a 'foodies' paradise but when it's done right up here it's really done right! If you decide to visit off-season you'll still be spoiled for choice.