Fall trip - Boston-Hampshire-Vermont-Maine - Itinerary suggestions - 5 Days
 

Planning to visit Boston-Hampshire-Vermont-Maine this fall 2018 mostly in 1st week of October for 5 days. Currently planning to fly down to Boston and fly out of Maine.
Requesting suggestions to form an Itinerary and identify a route plan. Our main priority is fall foliage and scenic drives

Suggestions appreciated.

Best is to do a search here on Fodors because this is a frequently asked question.
I always recommend an inland rivers cruise from Portsmouth NH. It's a great trip any time. You can walk to the dock from the parking garage and almost everywhere around Portsmouth is scenic. You need to find some back roads like Kittery to York (without going on Rt 1 which is outlet mall hell). You might explore Yankee magazine's website. Where you go depends on your interests. Do you want to walk on a beach? Visit a historic museum? Portsmouth has some great restaurants but Portland ME seems to beating out everyone as the most popular destination for dining.
In Portland, if Bite Into ME food truck is still parked at Fort Williams, they sell excellent lobster rolls and the view looking out to Casco Bay is beautiful. There is also a nice view from the north if you drive up the Eastern Promenade. Huge park popular with locals. Portland's Old Port Area should satisfy any desires to go shopping.

4 states in 5 days, that's a lot of driving. Are you planning to visit Boston at all or are you just hopping in the car and heading for the fall colors?

It's a very busy week for New England travel and you'll need to lock in your lodging soon. Have you got the car reserved?

Are you planning on flying out of Portland, ME? Five days is not very long for a visit and you can not visit that many states. If you are flying out of Portland you could leave Boston and drive up through the white mountains in NH for a few days (stay somewhere near North Conway so you can drive over the Kancamagus Highway and route 302)) then go over to the southern ME coast for a few days (stay near Portland so you could explore the area). Where ever you are going you need to look into lodging quickly as it is very busy that time of year.

You need to narrow your focus and get hotel reservations ASAP.

I am also planning on doing a fall NE trip into Boston for a week. I am planning an itinerary right now. I am trying to figure it out and am reading this trying to get ideas. To you I would suggest sticking to coastal towns. You can smash Boston into one day, run over to the Berkshires if you want and hit Lennox. Perfect for leaf peeping and super cute, a nice drive too. Fly over to Gloucester and zip in a tour of that coastal town and then scoot up north into NH and ME. Towns are not that far apart, even though they look like it on the map so don't be too daunted by that.

To give a more specific itinerary suggestion we need to know if you plan to spend a day in Boston or not, and do you have five full days, or is it five nights (so really four days).


But one possibility is spend one day driving from Boston to Vermont through southern NH (via Portsmouth and Concord - driving time that route is 3 and a half hours so full day with stops) and spend a night in southern Vermont somewhere (Newfane area). Then next day drive up through Vermont (Rt 100) to somewhere around Franconia NH (also 3 and a half hours drive time so full day with stops). Third day drive from there through the white mountains to Camden Maine (again, 3 and a half hours drive time so full day). Spend rest of your time between Camden and Portland and fly out of Portland.

This information is not at all accurate. I wouldn't suggest to either of you to run over to the Berkshires then zip over to Gloucester then scoot up to NH and ME. The states in New England are not as big as western states but they are not THATclose and there is a lot of traffic to deal with. With only 5 days you would be driving the entire time which does not seem to me to be a very enjoyable vacation.

Given that mapquest suggests I90 from Boston to Lenox, a 2 hour drive, I think the difficulty for visitors is knowing which highways are to be avoided and which aren't too bad. I do my best to never ever drive on I90. It's a very boring limited access highway. Maybe 2 hours is ok if you have a good reason to visit Lenox. Personally I think it is too far out of the way on limited time to go there and then return to the coast to visit Gloucester.
Boston to Portsmouth to Concord to Newfane is also a questionable route if you use Mapquest but that's because MapQuest always suggests Rt 101 from Portsmouth to Concord and I don't like that limited access highway either. If you take Rt 16 to Rt 4 from Portsmouth to Concord, it's a more scenic but slower route (3 hrs 45 minutes) but a great choice if you want to stop in antique shops. It also takes you past Wagon Hill Farm which is a great place for a short hike if you want to stretch your legs. From the road you can't see that there's a trail that leads to the water. You can do a loop along the shore and back to the farm house. MapQuest takes you south on I93 to west on I89 in Concord and eventually puts you on Rt 202/9 which is a country highway but you've bypassed Concord's attractive and walkable downtown and, more importantly, a couple of the prettiest towns in NH. If you follow signs to the hospital and then continue west you'll go thru Hopkinton (highly recommend the slight detour to Gould Hill Orchard which has a lovely view to distant mountains) and Contoocook. Take Rt 127 over to Rt 202 and you'll go by a small covered bridge. Rest of mapquest directions to Newfane are good enough. You've sacrificed some time but gain prettier scenery.

There are lots of places you can go without going to the congested tourist meccas. I always feel a bit sorry for the people crawling along highways on foliage weekends. I recommend finding a few spots you'd really like to visit whether it be Lenox or Jackson NH and putting more time into seeing the details, local places.

Thank you so much everyone for the fantastic suggestions, it really helped me a lot.

This is what I have put together now for my 4 day 3 nights trip.
Boston->NewFane->Woodstock->LakeChamplain->Burlington->Stowe->WhiteMountains->KancamagnusPass->Concord->Portsmouth->Boston.

I removed Maine from my plan since as suggested as it would make the trip very hectic.

Need suggestions for places in the above list which I can choose for my overnight stay.

Still an awful lot of driving in a very short period of time!

If you really want to visit Maine, you can take an Amtrak Downeaster train to Portland or even Freeport. The LL Bean store is within walking distance of the Amtrak station in Freeport. The Downeaster starts from the Boston North station.
In May last year, I drove from Rochester NY east across Vermont and New Hampshire finding geocaches in each. Before sunset, we had checked into a motel in York Maine. I found a couple of geocaches near the coastline before driving into Massachusetts for a couple more cache finds. I then drove into Rhode Island for a couple in Providence. We spent that night in New London CT. The next day we visited the Submarine museum before heading to western CT. After finding geocaches in CT, we drove all the way to north central PA (Wellsboro) where I attended my 50th High School reunion.
It all depends on how much of each state you want to see. The states of the Northeast are much smaller than the states of the West.
Over the past 13 years I have found geocaches in all 50 states plus DC

Foliage starts in the north and at higher elevations. I suggest for that reason you go Boston Concord NH White Mountains. I93 is actually kind of scenic and going north you'll see mountains getting closer. You can go I93, east over Kancamagus then south on Rt 16 to loop back to I93 via Tamworth/Sandwich to Meredith in a leisurely half day but the Kanc is going to be crowded and Conway will be mobbed and you'll be seeing enough trees without doing the Kanc. So from the White Mountains over to Stowe then Burlington south along Lake Champlain. Then whatever route you want to go west. Middlebury is a nice college town. From Bristol you can take a route thru the mountains east to Rt 100 but if you head to Warren (I remember route as more mountainous) you can stop at the Warren Country store. Enjoy lunch on the deck and walk out back to see the mini gorge. I would go to Norwich VT instead of Woodstock (tourist mecca) but you can do both. Norwich Inn is very nice with a popular bar and a good restaurant across the street. Head to Newfane then over to Keene and then to Concord NH. It will be a state hwy mostly 55 mph. Then Concord to Portsmouth (if you have time) then Boston.

I would cut out the Kanc to Conway loop. You are probably going to have a hard time finding lodging for single nights if your visit is over a weekend. If it's a weekend, I would eliminate all tourist meccas. If you are here on a Saturday, Vermont has several wonderful farmers markets: Montpelier, Brattleboro, Burlington, Norwich (my favorite) with music and prepared foods. Festive and yummy. There are some outstanding apple orchards in NH. Both Apple Hill in Concord and Gould Hill in Hopkinton (could be on your route to Concord) grow a huge variety of apples. Gould Hill is now making hard cider with tastings on the weekends.

Fantastic! Thanks for these details about the foliage, I have adjusted my route to move to the north then towards the south.
Got the accommodation and cars sorted as well.

Would welcome any further suggestions or ideas though.

Visit the Pumpkin People in Jackson, NH. Located at the east end of the Kancamangus Hwy.

Return of the Pumpkin People - Jackson New Hampshire Chamber of Commerce

Don't bother with Ben and Jerry's unless you want to eat ice cream with three thousand other people.

Enjoy!!! It is gorgeous part of the country anytime of the year but Fall is a phenomenal time to visit.