I personally find the drive on the interstate from Philadelphia to Boston very boring so in the wish to save 6 or more hours of driving time would fly from Philadelphia to Boston. If you were to land in boston on the 14th in the evening you would stay the night. On the 15th take the 1.5 hours drive to Portland and have some Maine lobster. From there drive up to Acadia National Park and do some hiking. Spend two days there and head east to Bethel Me (about 4 hours). Stay at the Chapman Inn because the owner bakes muffins and cinnamon rolls every morning and the rooms are very neat. This would be the 17th and you could drive up the mount washington auto road, which you can see over 100 miles from the summit of on a clear day. On the way down make sure that you do not only use your brakes. If you have a automatic transmission which you can manually change the gears on, shift down to second gear and the engine will slow down your tires without you having to use your brakes. You can return back to the hotel for the night and drive the hour and a half to Littleton with one night there. On the way back you could either drive down to the Berkshires through Vermont or down through Southern New Hampshire. If NH I recommend you hike Mt Monadnock although you should prepare for some cold weather at the top. I once hiked it the last weekend of April and it was 60's at the bottom and 35 degrees windy, and snowing at the top. There are many scenic routes through VT and you should use Rt 2 to drive from North Adams, MA back to Boston. Avoid 95 at all costs because it is the ugliest stretch of highway with the most beauty all around it. Also foliage will be in peak in late october in MA.

Hope this helps a little

I'll chime in and suggest you look for flights to Manchester, NH. That brings you closer to where you want to be. I would always recommend visiting Boston, but if that's not in your plans this trip, Manchester will be easier. Southwest flies there.

The drive north from PA should take your thru some nice color. I would take a that goes from Hartford up thru western MA to VT (I90) or up to Albany and over to Bennington VT then across to Brattleboro (southern VT). From Brattleboro cross over to Keene and then take Rt 101 that will get you to Mt Monadnock.

I agree with poster that I95 is ugly and a trip thru western MA is much more scenic.

PAY ATTENTION to weather and clothing requirements because that time of year can be dangerous because of hypothermia. Check the Audubon Society website for info on the hawk migration. http://www.nhaudubon.org/locations/raptor-observatories There is an observation area on Pack Monadnock and also near Concord NH. We haven't done this and I don't know why not since we love watching birds.

Peterborough is a beautiful town for a stop. You can continue on to the coast via Rt 101 but it's the most boring route in NH. If you want something more scenic, go north to Concord and head east on Rt 4. This approach will take you thru Dover Point and over the beautiful bridges that cross Great Bay. This will connect with I95 for your trip north to Acadia. Would suggest a stop in Portland for dining and shopping fun (Old Port Area). On the way north if you don't go I95 most of the way, you can stop in Rockland for the easy hike/walk to Owls Head Light etc. Visit Mt Battie just north of Camden. Don't forget binnoculars!

When you head south you can take the most direct route to Littleton or you can continue back to Portland and then west to NH. From Portland to NH Conway area is about an hour. You could take the Kancamagus Hwy over to I93 and then north to Littleton. I93 cuts thru White Mountains.

Littleton is right next to VT so after the wedding you could go over to VT and south. That would be a pretty drive any time of year. Keep in mind just about all of VT has a rural feel. In NH, from Concord south is pretty built up. I93 goes thru mostly wooded areas with little advertising (except for the state liquor stores) but once you get to the MA line, it will start to look very industrial.

Check conditions and open times. The Flume is a pricey tourist attraction but is a strenuous walk for a non-hiker and interesting enough for a hiker (I think). There are books on hiking in the White Mountains or you might get some good advice here on hikes from another poster. (Akislanders?)

Thank you, thank you, thank you for all your generous advice. It is so greatly appreciated. I'm going to sit down tonight with a map and plan my route based on all your wonderful advice.
Laurie

IMO Acadia is too out of the way with only one week.

Check out the hike to Lonesome Lake in the Franconia Notch area. It's very nice and there is an AMC hut where you can get a drink/snack. My four year old did most of it on his own, although it took a while. This is in NH by the way.

You could stop at King Arthur Flour in Norwich VT.

In Walpole NH, LA Burdick chocolate is a great place to check out...yummy too!

In Quechee VT there is a short "hike" to the gorge. There is also a Cabot cheese store there and Simon Pearce.

Sorry it's in a jumbled order....

No need to fly from Philadelphia to Maine. How about taking an Amtrak NE corridor train from PHL to BOS? Rent your car in Boston to go northeast to Maine. Make your loop with the rental car to NH to go to the second wedding. Return the car to Boston and fly home from there.
At that time of year, New Hampshire is not that much different from Vermont if you run short of time.

Thanks again for all the great suggestions. I think what makes this somewhat difficult is I only have so many days, and Philly and Acadia are so far apart. I think by the time we check our luggage and fly to either Boston or Manchester, wait for our luggage, and then rent a car we probably won't be saving that much time as we'd still have a fairly long way to drive. I like the train idea, but we wouldn't be able to check our luggage. Would there be a scenic place to stop between Philly and Portland to break up that loooong day.

Sun. - Wedding in Audubon, PA
Mon. ?
Tues. - Portland
Wed and Thurs - Bar Harbor (or the quieter side)
Fri. - Bethel
Sat - Wedding in Whitefield, NH

Is that crazy? Any suggestions for Mon?

Thanks,
Laurie

googlemaps says its 10 hours to Bar Harbor
It's about 6 hours to Portsmouth NH

Portsmouth is on the coast, has some terrific restaurant and with only 4 more hours to Bar Harbor you could take your time, say stop for lunch in Portland (if you're late sleepers and want to do a bit of sit seeing in southern Maine)
A slight detour to Owls Head Light to stretch your legs, maybe stop at the winery
Continue on Rt 1 to Bar Harbor with a stop at the top of Mt Battie.
But if you don't mind a slightly longer route to Portsmouth, I would go up thru western MA and across Rt 101 with a visit to Mt Monadnock (check out hawk viewing spot) then up to Concord and over to Portsmouth as described above.

The route thru western MA should be very pretty and perhaps you could stop sooner then Portsmouth esp if you wanted to do something along the way. Plus if you are driving over the Great Bay Bridges/Dover Pt area in the dark, it wouldn't be so pretty. Check what time sun sets that time of year.

My suggestion for Monday would be to get on the #190 Northeast Corridor train. It leaves PHL at 5:15AM and arrives at Boston South station (BOS) about 11AM. The fare for 2 of you would be $118 if you buy more than 2 weeks in advance.
Rent the car in Boston after eating lunch. You can be at Acadia before the sun goes down.
Don't get on the Acela for more than twice as much to save only 40 minutes on the trip,

Thanks everyone. I finally made a decision/commitment. I booked a 12:45 p.m. flight from Philly to Portland at a great rate of just $120 each. This will allow us to sleep in after the wedding and not have to face such a looooong drive. There is a 2-hour layover in D.C., but we get into Portland at 6:30, will have a late lobster dinner somewhere, stay the night, and get an early start the next morning. I've also booked 2 nights at Acadia Cottages. I can't thank you enough for taking up your valuable time and for all your great suggestions. I'm really looking forward to this trip and will, I'm sure, be back for more advice.