Another New England Newbie needs help with itinerary
 

That's an excellent time for leaves, all through NY, western MA, VT & NH. Much of Maine is more evergreen forest so the colors tend to be better MA/VT/NH. A Fri / Sat drive will be more crowded than weekday since it's peak leaf peeping season, but except for some congestion as you pass through small towns I think you'll be ok.

We drive to Boothbay a few times a year and personally I don't like the drive across VT/NH. Even though it's more miles we take I90 through Albany, loop around Boston then take I95 up through ME. Since you'll already be in VT & NH your route sounds ok.

Since you'll be in relax mode in BBH I would not try to squeeze in the Portland lighthouse the same day you arrive. Pemaquid (sp?) point lighthouse is not far from BBH, and there are others you can stop & see.

Let me know if you need more info for your week at the cabin.

The route across VT/NH is about 40 miles shorter distance and about 30min slower. It's a slower drive with more stopping along the way as you pass through small towns.
I have no interest in sightseeing along the way, just getting to the destination with the least hassle. Six hrs butts in car is already long enough - don't need to add to the misery.

Some things to note:
Foliage time is peak season in N.E. So, you will hit a lot of traffic going north, especially Boston north, on 95. 93 North will be busy too. However, since you mentioned Newburyport, that would be a lovely stop for your overnight on the 4th. It's a lovely historic town, and would be about 3-3.5 hrs from Boothbay. You could visit Plum Island while in NPort, walk the dunes, admire the historic seacaptain homes, and enjoy the town.

Then I'd head right for Boothbay Harbor. Don't miss the Botanical Gardens.

You will see plenty of leaves along the way, and just south of Boothbay is Camden, where you will find Mount Battie. An easy hike, if you like (about an hour up, an hour down) with views of the harbor.

There are plenty of small towns along the coast to stop and visit, an see some color, too.

However, I do understand the draw of the mountains in fall, and they are quite beautiful. With your short amount of time, I suggest you drop Vermont, and do perhaps NH and Maine, or just Maine itself.
The Kangamagus is indeed lovely in NH.

I would plan to head to Williamstown, MA on day 1. This will put you on MA route 2 which is the Mohawk Trail. Day 2 you can decide if you want to continue on rt 2 east to 495 then 95 N etc. to Boothbay, or to head north on 91 when you get to Greenfield and go into VT a way before going east through NH to get to Boothbay.

Make a reservation soon to stay in/near Williamstown as the lodging fills up during leaf peeping season.

I live in north central VT and that first week of October is usually peak foliage season here. The color peaks farther south a little later and would be considered "mid" in MA. This foliage map for New England gives you some idea of average times for good color
https://newengland.com/seasons/fall/...l-foliage-map/

Vermont does tend to be crowded that first weekend in October so you should definitely get lodging settled if you decide to take that route.

My apologies to J62 but I think the OP needs to figure where they will be during heaviest traffic times. NH I93 and I95 are always heavy during commuting times. Recently at 8:30 am on a Saturday northbound I95 in Seabrook area was already very heavy. It doesn't matter if the speed limit sign says 65. If there's a lot of traffic top speed might be 30.

According to google maps fastest speed might be a little more than 13 hours (using generic Roanoke and Boothbay Harbor) but 14 hrs 25 minutes if going north from Springfield MA via I91 to Brattleboro VT, then Keene to Concord NH and then east to Portsmouth/I95 via Rt 4 (had to drag route because google maps prefers Rt 101). I would avoid the Kancamagus on the weekend. Saturday travel to Boothbay is going to be tricky unless the OP gets an early start. The Keene to Concord NH route from Roanoke is almost 12 hours.

Keene is a great college town with some great restaurants. It might be a good choice for an overnight. Keene to Concord is state highways thru small towns and actually bypassing some. From Rt 202 you can take Rt 127 to Rt 103 thru the villages of Contoocook and Hopkinton NH with a slight detour to Gould Hill Farm for apples, hard cider, etc. (check hours for tastings) Then continue to Concord. Probably one of the most unique air b&bs would be in Loudon NH (look for pastoral farm) which is the Miles Smith Farm which raises Highland cattle. It would be a short detour but not far from getting to Rt 4 going east to Portsmouth/I95. Concord has two great bakeries (Crust and Crumb and Bread and Chocolate) but I think both would be closed in late afternoon. The cleaning fee makes one night at farm pricey. If a hotel is preferred the Marriott at Horseshoe Pond although it backs up to I93 is a beautiful walking area.

This route to Portsmouth takes you thru small towns and then Rt 16 at Dover Point area takes you over bridges, your first glimpse of water, before connecting with I95. Here's a list of popular cider donut places in NH https://www.10best.com/awards/travel...new-hampshire/

But, if you can stand it, getting closer to Boothbay on Friday might be the best idea. We usually fade around 8 hours in the car. I think timing on Friday is going to put you in commuter traffic at some point. Our goal is usually get thru Hartford CT during non-commuting hours. The gamble is also that the longer route will actually be faster due to less traffic. Last June on a Friday we traveled back from Sturbridge MA to Nashua NH after a long lunch and the traffic was horrible taking more than an hour longer (I90 to I495 ). Swore never to do that on a Friday again.

No apology necessary d. Your point about traffic is valid.
We've learned to time our drives to BBH specifically to avoid the traffic pinch points, and don't travel to ME on a Fri or Sat.

Coming from upstate NY the pinch points are Eastward bound
1. I90/I84 merge near Sturbridge. - usually only bad at the end of a holiday weekend.
2. I290 through Worchester & I495 through Lowell - avoid evening rush hour and end of holiday weekend.
3. I95 all through NH to ME border - avoid at all cost on Fri afternoon or summer Saturday except for early am. Generally we've not found issues with that section in the fall, and never in winter.
4. and the final stretch, Rt1 from Brunswick/Bath through Wiscasset - avoid weekends after 11am due pedestrians crossing the road in Wiscasset to get to the Reds. New traffic lights either planned or already completed are supposed to help with this.

We find if we can get past Lowell by early afternoon on a weekday then we have pretty smooth sailing.

Boothbay is not at all a good central locations for day trips out to see fall foliage. Nice place to stay and explore though.

Sounds like a good plan.

Rt7 East from Troy to VT is a pretty drive in the fall. One lane each direction over winding roads & rolling hills. You'll take I87 to Exit 23/Albany, then I787 North about 10miles from there to Troy where you'll pick up Rt7. The stretch from Albany to Troy can get backed up evening rush hour weekdays but it's not a long stretch.

The 1st day segment in VT especially the last ~1hr from Manchester to your Airbnb in Brownsville may be a bit tough after dark especially when you're tired. Sunset is ~6:30. An alternative which would add 40 more miles (but no more total driving time) is I87 to I90 to I91 up to Brownsville area. You can make that a game time call - but if you're going to hit that area at dusk/dark anyway the interstate would be an easier drive. Your decision point is Ex21A, about 15mi south of Albany where you'd the NYS Thruway/Berkshire connector east to pick up I90.

You'd still have all of your 2nd day for great sightseeing drives across VT/NH/ME.

If it's Saturday and you are going thru Norwich - I love King Arthur Flour but the farmers market opens at 9am and it's probably one of the best in New England. There are several prepared food vendors so you could have breakfast there. I usually get a pastry but the website says they have breakfast sandwiches. Norwich Farmers' Market - Home

12 hours of driving is not a "bit long", it's exhausting. Ten hours is about my limit, especially if you want so see or do anything at all along the way....like a meal for instance.