New York - New England Road Trip
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New York - New England Road Trip
Hello!
My wife and I are planning for a 2 week (13 days to be exact minus the flying) road trip which starts and ends from New York, EWR airport (We are sitting the new direct flight by Singapore Airlines from Singapore). The trip will be from end Oct to mid Nov, exact dates as shown below. I've done some research, and have came out with a draft plan as shown below.
My wife and I loves nature and enjoy strolls and "gentle" hikes. I know it is a little late in the fall season to catch the peak foliage, but unfortunately we will not be able to leave any earlier. We prefer quiet towns as opposed to busy cities, which is why I did not allocate much time in Boston and New York. We do like some shopping as well, and I have four outlets marked along the route (The Kittery Outlets, Settlers Green Outlet Village, Manchester Designer Outlets. Woodbury Common Premium Outlets). And of course, we enjoy great food!
27 Oct - Flight out from Singapore.
28 Oct - Arrive in New York EWR Airport. Depart for Boston via Amtrak.
29 Oct - Boston
30 Oct - Boston to Portland via US highway 1. Will rent a car from here. Will stop along places like Portsmouth, Ogunquit and Kennebunkport (not sure if there is enough time to stop at so many places?).
31 Oct - Portland to Bar Harbor via US highway 1. Will stop along Camden.
01 Nov - Bar Harbour / Acadia National Park
02 Nov - Bar Harbour / Acadia National Park
03 Nov - Bar Harbor to Jackson (White Mountains).
04 Nov - Jackson
05 Nov - Jackson to Manchester (Green Mountain and Finger Lake). Will drive through Route 112.
06 Nov - Manchester
07 Nov - Manchester to New York City. Will return the car at New York City.
08 Nov - New York City
09 Nov - New York City
10 Nov - Morning flight out of New York EWR Airport.
Let me know if the above itinerary is feasible at a comfortable pace, and any scenic routes/stops to recommend along the way as opposed to the fastest interstate route. Also any potential road closures to take note during that period, and if I am going to encounter closure of services/places at many areas which might make this trip not worth taking in Nov.
Lastly, if I am able to add 2 more days to this itinerary (wife negotiating with her boss!), where would you suggest to add/change/give more time? Perhaps an additional day along the Portsmouth - Ogunquit - Kennebunkport - Portland route, or in one of the major cities?
Thank you very much!
My wife and I are planning for a 2 week (13 days to be exact minus the flying) road trip which starts and ends from New York, EWR airport (We are sitting the new direct flight by Singapore Airlines from Singapore). The trip will be from end Oct to mid Nov, exact dates as shown below. I've done some research, and have came out with a draft plan as shown below.
My wife and I loves nature and enjoy strolls and "gentle" hikes. I know it is a little late in the fall season to catch the peak foliage, but unfortunately we will not be able to leave any earlier. We prefer quiet towns as opposed to busy cities, which is why I did not allocate much time in Boston and New York. We do like some shopping as well, and I have four outlets marked along the route (The Kittery Outlets, Settlers Green Outlet Village, Manchester Designer Outlets. Woodbury Common Premium Outlets). And of course, we enjoy great food!
27 Oct - Flight out from Singapore.
28 Oct - Arrive in New York EWR Airport. Depart for Boston via Amtrak.
29 Oct - Boston
30 Oct - Boston to Portland via US highway 1. Will rent a car from here. Will stop along places like Portsmouth, Ogunquit and Kennebunkport (not sure if there is enough time to stop at so many places?).
31 Oct - Portland to Bar Harbor via US highway 1. Will stop along Camden.
01 Nov - Bar Harbour / Acadia National Park
02 Nov - Bar Harbour / Acadia National Park
03 Nov - Bar Harbor to Jackson (White Mountains).
04 Nov - Jackson
05 Nov - Jackson to Manchester (Green Mountain and Finger Lake). Will drive through Route 112.
06 Nov - Manchester
07 Nov - Manchester to New York City. Will return the car at New York City.
08 Nov - New York City
09 Nov - New York City
10 Nov - Morning flight out of New York EWR Airport.
Let me know if the above itinerary is feasible at a comfortable pace, and any scenic routes/stops to recommend along the way as opposed to the fastest interstate route. Also any potential road closures to take note during that period, and if I am going to encounter closure of services/places at many areas which might make this trip not worth taking in Nov.
Lastly, if I am able to add 2 more days to this itinerary (wife negotiating with her boss!), where would you suggest to add/change/give more time? Perhaps an additional day along the Portsmouth - Ogunquit - Kennebunkport - Portland route, or in one of the major cities?
Thank you very much!
Last edited by Linus1987; Jul 17th, 2018 at 07:30 PM.
#2
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The bad news is we can have some very rainy weather starting mid-October. Just cross your fingers and hope for the best.
Do not take Rt 1 all the way from Boston to Portland. It will take forever and have a lot of local traffic even that time of year. Take I95 but get off in Portsmouth NH. Have lunch some place, there are lots of choices in the Market Square area. You could take Rt 1 to Kittery which is just over the bridge. Shopping is going to take some time but you have only allotted one day to get to Portland. Get back on I95 to Portland or continue Rt 1 to Kennebunkport. If you have to choose one, that's the one I would pick over Ogunquit.
Rt 1 is a very old turnpike so again, I advise taking I95/295 north at least as far as Brunswick. Lobster "shacks" will be closed but there are plenty of year round restaurants and Brunswick offers a lot.
I think you are going to have to make a decision about going to Acadia. If the weather is dismal, I would spend time elsewhere. It is also a long drive and your on limited time. I also think Rt 112, the Kancamagus Hwy is not a good choice because of the time of year. If you go further south via Rt 16 to Tamworth and then west thru the town of Sandwich, I think it will be a more interesting drive. It's my favorite any time of the year. Then head to Moultonborough and Meredith. Meredith has a nice little shopping area plus a grand view of Lake Winnipesaukee. Then maybe south on I93 and find your way to Rt 11 which will be less traveled road and will take you to the charming college town of New London. There's different options for getting to Manchester VT from there but none seem to stand out.
Do not take Rt 1 all the way from Boston to Portland. It will take forever and have a lot of local traffic even that time of year. Take I95 but get off in Portsmouth NH. Have lunch some place, there are lots of choices in the Market Square area. You could take Rt 1 to Kittery which is just over the bridge. Shopping is going to take some time but you have only allotted one day to get to Portland. Get back on I95 to Portland or continue Rt 1 to Kennebunkport. If you have to choose one, that's the one I would pick over Ogunquit.
Rt 1 is a very old turnpike so again, I advise taking I95/295 north at least as far as Brunswick. Lobster "shacks" will be closed but there are plenty of year round restaurants and Brunswick offers a lot.
I think you are going to have to make a decision about going to Acadia. If the weather is dismal, I would spend time elsewhere. It is also a long drive and your on limited time. I also think Rt 112, the Kancamagus Hwy is not a good choice because of the time of year. If you go further south via Rt 16 to Tamworth and then west thru the town of Sandwich, I think it will be a more interesting drive. It's my favorite any time of the year. Then head to Moultonborough and Meredith. Meredith has a nice little shopping area plus a grand view of Lake Winnipesaukee. Then maybe south on I93 and find your way to Rt 11 which will be less traveled road and will take you to the charming college town of New London. There's different options for getting to Manchester VT from there but none seem to stand out.
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Good advice fro dfrostnh. One eye should always be on the weather as in addition to rain we have had snow at that time of year. If you have not driven in the snow and it is forecast, the farther north, the more likely, have a plan B.
Perhaps visit places like Cape Cod, MA, Newport, RI, Mystic, CT, etc as they are farther south and near the coast where snow is less likely.
Perhaps visit places like Cape Cod, MA, Newport, RI, Mystic, CT, etc as they are farther south and near the coast where snow is less likely.
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November can be a dismal time in northern New England - everything is grey and brown, and sleet and snow is possible. Of course, you could also have some nice weather, but it will still be chilly. Acadia is a very long drive, you might want to consider exploring the Ogunquit, York, Kennebunkport area of Maine instead. The suggestion to be further south is a good one as it will be a little warmer - Cape Cod will be empty this time of year, you will have miles of deserted beaches to walk. Also - 'Finger lakes' is not anywhere near New England, this is a typo on several internet maps.
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I wouldn't be too alarmed about the weather as you will be going in early November. Yes, there is a slight possibility of light snow but it won't be too bad along the coast. We have done that trip numerous times that time of year and never had an issue. I agree you do not want to take Route 1 the entire trip, it would take forever! Take the highway to Portsmouth and then get off to visit that area and perhaps shop in Kittery. Get back on the highway and head towards York. You could then drive along the coast from York through Ogunquit (take a walk on the Marginal Way) up to Kennebunkport and then stay in Portland. The next day you could drive Route 1 along the coast up to Camden and have lunch (about 1 hour 45 minutes to Camden if you don't stop, which you will want to do). You could then drive on to Bar Harbor and Acadia. It is a beautiful drive and Acadia is beautiful any time of year. Some things will be closed due to the time of year but there will still be things open in Bar Harbor and the advantage is there will be no crowds!
The drive to Jackson will be a bit long but you will pass through some nice towns once you get off the highway. Jackson is a beautiful area. The day you are there you should drive up 302 and stop at the Mount Washington Hotel. You could actually do a loop and leave from Jackson, go up 302 and then come back the Kancamangus (Route 112 back to Jackson). When we have company we often do that loop in a day as it is a beautiful drive. When you leave you could do as dfrostnh says and head down to Lake Winnipesaukee. It is also a beautiful section of NH. I have never been to Manchester, VT so I'm no help there.
Cape Cod is beautiful too but it sounds like you have your heart set on Maine. If that's what you want to do then go for it! If you have an extra day or two you might want to spend another night in Boston. Boston is a small city as cities go and is very walkable. There is a lot of history there, lots of restaurants and many things to do. Hope you have a great trip!
The drive to Jackson will be a bit long but you will pass through some nice towns once you get off the highway. Jackson is a beautiful area. The day you are there you should drive up 302 and stop at the Mount Washington Hotel. You could actually do a loop and leave from Jackson, go up 302 and then come back the Kancamangus (Route 112 back to Jackson). When we have company we often do that loop in a day as it is a beautiful drive. When you leave you could do as dfrostnh says and head down to Lake Winnipesaukee. It is also a beautiful section of NH. I have never been to Manchester, VT so I'm no help there.
Cape Cod is beautiful too but it sounds like you have your heart set on Maine. If that's what you want to do then go for it! If you have an extra day or two you might want to spend another night in Boston. Boston is a small city as cities go and is very walkable. There is a lot of history there, lots of restaurants and many things to do. Hope you have a great trip!
#6
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Very much thanks for all your responses. I've been quiet lately due to work and finally had some time to go back researching for my trip. I've just booked my flights, very excited!
I've tweaked my itinerary, main changes are starting with NYC instead of ending with it, reason being I can return the car straight @ EWR when i depart from NYC (vs having to drag luggage from Manhattan if i were to leave touring NYC to the last). I've also removed Boston after reviewing the things to do and being not really interested in universities and history (I know Freedom Trail is a must-do), and replacing it with Provincetown Cape Cod.
My revised itinerary is as follows:
27 Oct (Sat): Arriving in New York EWR @ 6am. New York (Museum of Natural History, Central Park)
28 Oct (Sun): New York (Midtown)
29 Oct (Mon): New York (Statue of Liberty, 9/11 Memorial, Brooklyn Bridge)
30 Oct (Tue): Rent a car from Manhattan. Drive to Provincetown Cape Cod, with a stop for lunch @ Newport.
31 Oct (Wed): Cape Cod
01 Nov (Thu): Provincetown Cape Cod - Portsmouth (For lunch and some outlet shopping @ Kittery) - Portland
02 Nov (Fri): Portland - Camden - Bar Harbour (Acadia National Park)
03 Nov (Sat): Bar Harbour (Acadia National Park)
04 Nov (Sun): Bar Harbour (Acadia National Park)
05 Nov (Mon) - Bar Harbor - Jackson (White Mountains).
06 Nov (Tue): Jackson (White Mountains)
07 Nov (Wed): Jackson to Manchester (Green Mountain). Will drive through Route 112.
08 Nov (Thu): Manchester (Green Mountain)
09 Nov (Fri): Manchester - WoodBury Common Outlets - Newark
10 Nov( Sat): Return Car @ EWR Airport. Flight @ 9.45am.
Will welcome any advice.
I've tweaked my itinerary, main changes are starting with NYC instead of ending with it, reason being I can return the car straight @ EWR when i depart from NYC (vs having to drag luggage from Manhattan if i were to leave touring NYC to the last). I've also removed Boston after reviewing the things to do and being not really interested in universities and history (I know Freedom Trail is a must-do), and replacing it with Provincetown Cape Cod.
My revised itinerary is as follows:
27 Oct (Sat): Arriving in New York EWR @ 6am. New York (Museum of Natural History, Central Park)
28 Oct (Sun): New York (Midtown)
29 Oct (Mon): New York (Statue of Liberty, 9/11 Memorial, Brooklyn Bridge)
30 Oct (Tue): Rent a car from Manhattan. Drive to Provincetown Cape Cod, with a stop for lunch @ Newport.
31 Oct (Wed): Cape Cod
01 Nov (Thu): Provincetown Cape Cod - Portsmouth (For lunch and some outlet shopping @ Kittery) - Portland
02 Nov (Fri): Portland - Camden - Bar Harbour (Acadia National Park)
03 Nov (Sat): Bar Harbour (Acadia National Park)
04 Nov (Sun): Bar Harbour (Acadia National Park)
05 Nov (Mon) - Bar Harbor - Jackson (White Mountains).
06 Nov (Tue): Jackson (White Mountains)
07 Nov (Wed): Jackson to Manchester (Green Mountain). Will drive through Route 112.
08 Nov (Thu): Manchester (Green Mountain)
09 Nov (Fri): Manchester - WoodBury Common Outlets - Newark
10 Nov( Sat): Return Car @ EWR Airport. Flight @ 9.45am.
Will welcome any advice.

#7
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I do not think your replacement with Cape Cod is very doable. Provincetown is on the tip of Cape Cod and is a long drive. All you will be doing is driving onto the Cape and then back off of it. The drive from Provincetown to Portsmouth is also quite long. Why don't you stay in Newport if you are stopping there for lunch. It is a beautiful time of year to be there as there will be less people. You could visit some mansions, do the cliff walk, enjoy the restaurants and the area. It is a destination in itself and that time of the year on the Cape you might find a lot of things closed. If you do go to the Cape stay in Chatham. It is not so far out on the Cape and is a beautiful town.
#8
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Thank you Sberg. You made me rethink my itinerary more, and maybe heading straight to Portsmouth from NYC will free up some travelling time and allow me to spend more time on the eastern coast of NH & Maine. Newport was meant to be only a stopover if im heading towards Cape Cod.
I've changed the "30 Oct to 02 Nov" portion of the trip as follows:
30 Oct (Tue): Rent a car from Manhattan. Early morning drive to Portsmouth.
31 Oct (Wed): Portsmouth - Kittery - Ogunqit - Kennebunkport - Portland
01 Nov (Thu): Portland & Cape Elizabeth
02 Nov (Fri): Portland - Camden - Bar Harbour (Acadia National Park)
How does it look? What will be the best time to leave Manhattan on a Tue morning, and what is a good stopover between NYC and Portsmouth?
Thanks!
I've changed the "30 Oct to 02 Nov" portion of the trip as follows:
30 Oct (Tue): Rent a car from Manhattan. Early morning drive to Portsmouth.
31 Oct (Wed): Portsmouth - Kittery - Ogunqit - Kennebunkport - Portland
01 Nov (Thu): Portland & Cape Elizabeth
02 Nov (Fri): Portland - Camden - Bar Harbour (Acadia National Park)
How does it look? What will be the best time to leave Manhattan on a Tue morning, and what is a good stopover between NYC and Portsmouth?
Thanks!
#9
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I’m not sure there is ever a good time to drive in or out of NYC but I am not the best person to ask as whenever I drive through there I try to be on the other side by 6 a.m! Hopefully someone else can give more information as I tend to avoid that area.
The drive from there to Portsmouth is all highway and pretty boring but it is the quickest and best route ( don’t take back roads as it will take forever!) Depending when you get there Sturbridge might be a good place to stop.
I think your decision to drop the Cape is a good one. You are trying to cover too much area if you try to do the Cape and Maine.
The drive from there to Portsmouth is all highway and pretty boring but it is the quickest and best route ( don’t take back roads as it will take forever!) Depending when you get there Sturbridge might be a good place to stop.
I think your decision to drop the Cape is a good one. You are trying to cover too much area if you try to do the Cape and Maine.
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Thank you Sberg. You made me rethink my itinerary more, and maybe heading straight to Portsmouth from NYC will free up some travelling time and allow me to spend more time on the eastern coast of NH & Maine. Newport was meant to be only a stopover if im heading towards Cape Cod.
I've changed the "30 Oct to 02 Nov" portion of the trip as follows:
30 Oct (Tue): Rent a car from Manhattan. Early morning drive to Portsmouth.
31 Oct (Wed): Portsmouth - Kittery - Ogunqit - Kennebunkport - Portland
01 Nov (Thu): Portland & Cape Elizabeth
02 Nov (Fri): Portland - Camden - Bar Harbour (Acadia National Park)
How does it look? What will be the best time to leave Manhattan on a Tue morning, and what is a good stopover between NYC and Portsmouth?
Thanks!
I've changed the "30 Oct to 02 Nov" portion of the trip as follows:
30 Oct (Tue): Rent a car from Manhattan. Early morning drive to Portsmouth.
31 Oct (Wed): Portsmouth - Kittery - Ogunqit - Kennebunkport - Portland
01 Nov (Thu): Portland & Cape Elizabeth
02 Nov (Fri): Portland - Camden - Bar Harbour (Acadia National Park)
How does it look? What will be the best time to leave Manhattan on a Tue morning, and what is a good stopover between NYC and Portsmouth?
Thanks!
On this route, Sturbridge would be out of the way otherwise I agree it would be a good stop for lunch or late breakfast.
#11
Car rentals in Manhattan can be unexpectedly expensive. Also, where will you return the car and will there be a fee for returning the car elsewhere? Consider a train to Boston or your first goal and renting a car there.
#12
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Our preferred route is up thru Hartford CT and Springfield MA then I91 to Brattleboro VT then to Portsmouth. According to google maps, this route takes 30 minutes more than the recommended routes like I95 thru MA. Be advised you don't want to go thru Hartford during commuting hours. Once you are north of Springfield MA is will be very rural. From Brattleboro east it will be very rural but mostly 55mph roads until Rt 202 joins up with I89 west of Concord NH.
On this route, Sturbridge would be out of the way otherwise I agree it would be a good stop for lunch or late breakfast.
On this route, Sturbridge would be out of the way otherwise I agree it would be a good stop for lunch or late breakfast.
Thanks AJPeabody! Yes, rental in Manhattan is a little more expensive than Boston, but after some calculations it is still cheaper than buying 2 Amtrak Tickets (even early bird price) from NYC to Boston. No I will not incur drop off fees as I'm renting in Manhattan and returning at EWR Airport. I will incur drop off fees if I rent in Boston and return at EWR Airport.
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I think it would add an hour to the route to go through Vermont but it would be a more scenic route, as we all know that driving on the highway is not so pretty, but it is quicker. I guess it depends how long you want to spend getting to Portsmouth. Hartford traffic could be bad from about 7:00 through 9:30. No guarantee on traffic on any of the roads through Connecticut as they are very heavily traveled at many times of the day.
#14
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I think it would add an hour to the route to go through Vermont but it would be a more scenic route, as we all know that driving on the highway is not so pretty, but it is quicker. I guess it depends how long you want to spend getting to Portsmouth. Hartford traffic could be bad from about 7:00 through 9:30. No guarantee on traffic on any of the roads through Connecticut as they are very heavily traveled at many times of the day.
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Yes, the VT route is much more scenic and we rarely encounter traffic. I generally dislike the Mass Turnpike I90 which is east/west so you can be driving directly into the sun at certain times of the day. It is a very limited access highway with exits many miles apart. We live in NH where the VT route makes life easier. We hate traffic. There's a gas station in NH just east of the CT river after leaving VT that we like stopping at. When our son used to visit from NC he would take this route. It was probably more relaxing after dealing with several hundred miles of traffic. Keep in mind once east of Keene NH, there's isn't much in the way of gas stations or fast food places until you get to Hillsborough or Concord.
I also greatly dislike google maps quickest route from Concord to Portsmouth via limited access boring Rt 101. We take I393 to Rt 4 to Rt 16 approaching Portsmouth from the west. Again, it's a 35-55 mph country highway with places to stop if you need (including a couple of traffic lights) but after you go thru Durham you are in beautiful country going past Wagon Hill Farm and the exit to Dover Point. There's some construction but it doesn't seem to be a problem except for ruining the view. You go over bridges so it's the first look at water and fishing boats. If you've been alert, you've noticed the "rivers" you've driven past are saltwater tidal rivers. If you take I95 you don't see water until you go from Portsmouth to Kittery ME. Rt 4 goes thru towns which slows things down but Rt 101 bypasses all the towns.
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Keep in mind we live in a rural area so heavy traffic is bothersome. If you can deal with the maybe half hour of Hartford rush hour, it might be worth it to get an early start to get to NH and ME as soon as possible. We always breathe a sigh of relief to get north of Springfield MA.
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You wouldn't have to leave NY at late as 10:00. You can check the traffic reports and leave as soon as you can reasonable get out, maybe 8:30 or 9:00. I don't know where you would be staying, if it is downtown or outside the city. There are a few different routes to leave the city and travel through CT. I would check with some local people before you leave.
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I can't speak to many of the places you are considering. But I wanted to address one misconception about Boston--while the Freedom Trail is fascinating and obviously a key part of the city, there is much more to the city and its outlying areas. One of my favorite days of travel as a young adult was visiting Concord. We toured Louisa May Alcott's house, went to Walden Pond, saw Hawthorne's house and ate at a really old pub in the area. A charming area with a lot of trees near the authors' homes. You might consider it on a future trip.
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