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SirSaintly
New Orleans Saints Fan
Uptown, New Orleans
Member since Feb 2013
2882 posts

Need Help Planning 7 Day Road trip to New England
We're planning a 7 Day road trip to New England from 10/9 thru 10/16.

Planning on flying into and out of Boston Logan as I've found it's cheaper than smaller airports and American flies there direct. Coming from DFW btw.

One caveat, I have 120,000 Hyatt points so hoping to stay mostly at Hyatt's if possible.

Here's what I have so far:

Fly into Boston 10/9 around 1pm. Pick up rental car and drive to Warwick, RI(Hyatt here). Do a day trip to Newport on 10/10.

Wife is interested in Provincetown, but it's a 2 hr drive from Warwick. If she gets her way, we'll do that 10/11, but I'd rather get headed towards ME.

Check out of Hyatt Warwick on 10/11 or 10/12 and this is where I get lost. We went to go to Portland, Kennebunkport, and Freeport in ME. What's a good scenic loop that would get us there, possibly going through VT or NH? Plan on 2 days at the Hyatt in Portland(would do day trips to Freeport and Kennebunkport from here). Would leave about 10/14.

Want to make a stop in Salem and then 2 days in Boston before flying out.

Not opposed to checking out Nantucket or Martha's Vineyard instead of P-Town if that's more on the way of this road trip?

Main things we definitely want to do is Portland and Boston, but I figured 7 days gives us time to hit up some other areas.

Not opposed to altering this itenary as I've never been to New England before and I may be trying to squeeze in too much.

Please help me figure this out


soccerfüt
Location: A Series of Tubes
Member since May 2013
48316 posts

re: Need Help Planning 7 Day Road trip to New England
It sounds like you’re trying to get 18 eggs to fit into a dozen egg carton.

Nantucket or Martha’s Vineyard are wonderful in Fall, but you need to spend at least a night on either and the whole day before & after.

Woods Hole (near Kennebunkport) is nice too, Kennebunkport is where the Nantucket ferry lands.

The manor houses in Newport are interesting to see, Boston is chock full of sights and very walkable.

The foliage will probably be already past peak, but who knows?

Get with your wife and pare down the list to three or four destinations.


AbitaFan08
LSU Fan
Boston, MA
Member since Apr 2008
21928 posts

re: Need Help Planning 7 Day Road trip to New England
quote:

It sounds like you’re trying to get 18 eggs to fit into a dozen egg carton.


Bingo.


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nctiger71
LSU Fan
North Carolina
Member since Oct 2017
924 posts

re: Need Help Planning 7 Day Road trip to New England
quote:

We went to go to Portland, Kennebunkport, and Freeport in ME.

Are you going to Freeport to go to L .L. Bean?


AbitaFan08
LSU Fan
Boston, MA
Member since Apr 2008
21928 posts

re: Need Help Planning 7 Day Road trip to New England
quote:

Are you going to Freeport to go to L .L. Bean?


Maine Beer Co. is a more worthy stop whilst in Freeport.


nctiger71
LSU Fan
North Carolina
Member since Oct 2017
924 posts

re: Need Help Planning 7 Day Road trip to New England
quote:

Maine Beer Co. is a more worthy stop whilst in Freeport.
I’m sure that’s right. We stopped by L. L. Bean on the way from Bar Harbour to Portland and it’s just a store IMO. Good to know there’s something else to do there.


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SirSaintly
New Orleans Saints Fan
Uptown, New Orleans
Member since Feb 2013
2882 posts

re: Need Help Planning 7 Day Road trip to New England
quote:

Are you going to Freeport to go to L .L. Bean?




Yep. Have always wanted to go to the Flagship. It's only 20 mins from Portland so figured I'd spend an hour there.

I'm now also considering flying into Portland and out of Boston or Providence. Figured that would save some unneeded driving but flights are pretty high right now and I can't find any direct flights to either of the smaller cities. Would rather not spend 6+ hrs flying aroundb making stops and connections on that first day. Thats the main reason we're looking at Logan although I'd prefer either Providence to Portland or vice versa.

If we can find decent airfare we'd do:

Portland, ME(day trips to Kennebunkport, Freeport, etc)

Salem, MA(a half day)

Boston, MA

Newport, RI

Providence, RI

Or the reverse

Is Newport worth the trip or should I just concentrate on MA, ME, and maybe some NH?



McVick
Michigan Fan
Member since Jan 2011
3633 posts
 Online 

re: Need Help Planning 7 Day Road trip to New England
quote:

Woods Hole (near Kennebunkport) is nice too, Kennebunkport is where the Nantucket ferry lands.



Wait, what?
I know Woods Hole is near Falmouth on the Cape, and there is a ferry from Woods Hole to Martha's Vineyard but I didn't think there was a ferry from Woods Hole to Nantucket. And Kennebunkport is nowhere near Woods Hole. Maybe you were thinking of Hyannis Port, the location of another presidential family compound?
This post was edited on 5/5 at 6:20 am


soccerfüt
Location: A Series of Tubes
Member since May 2013
48316 posts

re: Need Help Planning 7 Day Road trip to New England
Yep, my bad. High anus port.

I sit corrected.


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longhorn22
North Carolina Fan
Nicholls St. Fan
Member since Jan 2007
39905 posts

re: Need Help Planning 7 Day Road trip to New England
Me and the wife did a road trip in cali a few months back, enjoyed that type of trip...

Told her one of my next road trips was the NE area... so definitely will be following this thread.. hope you button it up some and narrow it down so its easier to follow, lol... currently sounds like you're trying to cram alot into a little... might be best to do the trip in 2 and just go back that way another time..


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nicholastiger
LSU Fan
Baton Rouge
Member since Jan 2004
25173 posts
 Online 

re: Need Help Planning 7 Day Road trip to New England
Newport Rhode Island and the large mansions is a good first stop
I would skip Provincetown
You could maybe take the ferry to Martha's Vineyard or Nantucket for a day trip or just explore the southern part of Cape Cod like Hyannis, Chatham, Yarmouth, Dennis, etc.

From there you could make your way up and briefly stop in Salem and also Marblehead, Rockport MA and Gloucester are right there.

Once you get to New Hampshire you could get off at Portsmouth and make you way up coastal area of York and Kennebunkport Maine.

From there it's not far from Portland and Freeport.


McVick
Michigan Fan
Member since Jan 2011
3633 posts
 Online 

re: Need Help Planning 7 Day Road trip to New England
This question gets asked about every year for summer trips and Fall Foliage season. I'm too lazy and don't have much time to devote to a proposed project all by myself, but from the collective knowledge of some of the posters here we could create a New England tour guide. And in my mind it could be broken down into two parts- Coastal New England and Northern New England/Mountains. Each of these areas can have an itinerary for a week of travel and could be linked for trips longer than seven days.


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nctiger71
LSU Fan
North Carolina
Member since Oct 2017
924 posts

re: Need Help Planning 7 Day Road trip to New England
TD Travel Board Fall 2020 Road Trip post
This is a link to a travel board road trip from last fall. Or you can google Tigerdroppings Travel New England and find it. It might be helpful for you.

When we left Portland to drive home we went to Conway New Hampshire. Spent the night there and took the Kancamagus Highway to Lincoln NH, and then into Vermont and then south. You could do something similar but go to Boston.

I've been there once. Take that for what it's worth. But this is what I would do.
Fly into Boston
Drive to Portland - 2 nights
Drive to North Conway - 2 nights
Drive to Boston - 3 nights,
Fly home

Get off the interstates as much as possible. Don't be in a hurry to get anywhere.


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JonTheTigerFan
LSU Fan
Central, LA
Member since Nov 2003
6074 posts
 Online 

re: Need Help Planning 7 Day Road trip to New England
My wife and I went a couple summers ago. Flew into Boston and stayed there 3 nights. Rented a car and drove to Newport, RI for one night. Drove to New Hampshire and went to Mt. Washington and stayed there 1 night. Drove to Portland, ME and stayed there 2 nights. Was a great trip even though it was a lot of driving and moving around but that’s kinda what we like to do anyway.


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SDVTiger
Hawaii Fan
Cabo San Lucas
Member since Nov 2011
52248 posts
 Online 

re: Need Help Planning 7 Day Road trip to New England
quote:

Pick up rental car and drive to Warwick, RI(Hyatt here). Do a day trip to Newport on 10/10.

Wife is interested in Provincetown


P Town is a must

Also Nordic Lodge for all you can eat Lobster (GOAT)


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Tigers13
LSU Fan
New Orleans
Member since Feb 2005
1444 posts

re: Need Help Planning 7 Day Road trip to New England
quote:

Salem, MA(a half day)


We did a half day stop here.....I would do something else. Plymouth Rock was a better quick stop.


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The Boat
Duke Fan
Tim McGraw Country
Member since Oct 2008
128566 posts

re: Need Help Planning 7 Day Road trip to New England
quote:

We're planning a 7 Day road trip to New England from 10/9 thru 10/16.

quote:

Planning on flying into and out of Boston Logan

Wut


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AbitaFan08
LSU Fan
Boston, MA
Member since Apr 2008
21928 posts

re: Need Help Planning 7 Day Road trip to New England
I've commented a couple times in this thread but haven't had time to give actual advice until now.

First, I do agree with what others have said already: you're trying to do too much in a week. You'll waste so much time driving and you'll be in these places so briefly that it won't be worth it.

I'd allot 2 full days for Boston, either on the front end or the back end of the trip (assuming you fly in and out of Logan). Normally I'd argue 3 days, but with only 7 for the trip and so many places on your list I think 2 is best.

As for Newport: it's a great little town and worth going to for a day/night. However, the one down side is that you're going the exact opposite direction of everywhere else you're looking to go, so to get from Newport to say, Kennebunkport, is going to take you at least 3 hours, probably longer.

Since you mentioned that Portland is a top priority (as it should be, I love Portland), I personally think you would be best served going north from Boston and hitting up a small place in Vermont for a night, then go to Kennebunkport for the day and getting to Portland that same night. Then spend a couple days in Portland (including a very short drive to Freeport since you want to go to LL Bean) before making your way back to Boston to head home.

If you're lucky, we'll get an unseasonably warm summer/early fall and you will have the chance to drive through during the foliage season, but usually that ends in mid to late September so I wouldn't count on it.

So essentially, the itinerary would look something like:

10/9-10/11 Fly into Boston and do stuff here
10/12: Drive to somewhere in southern Vermont for the day/night
10/13: Drive to Kennebunkport for the day, then go to your hotel in Portland that night
10/14-10/15: Spend in Portland and drive over to Freeport
10/16: Head back to Boston to fly home


Obviously this is just my $0.02, and you should do whatever you like. After all it's your vacation!

But doing the Cape in October isn't really worth it. And Newport, though a great town, would really derail the rest of the trip with all the extra driving.

Oh, and Salem is absolutely not worth it. Don't waste your time.

This post was edited on 5/5 at 6:01 pm


McVick
Michigan Fan
Member since Jan 2011
3633 posts
 Online 

re: Need Help Planning 7 Day Road trip to New England
As usual I agree with Abita. The Cape is pretty packed up and starting to get quiet that time of year. Also consider 2-3 nights in Boston, drive up the coast to Portland for 2 nights, then the rest of the time making a loop through NH and VT using Route 302 to go through Crawford Notch. Portland to Franconia is a little less than 3 hours, and then you can decide to either go down I-93 through Franconia Notch towards Lake Winnipesaukee (Wolfboro) or keep going west whichever way you want to VT towards Stowe or Warren/Sugarbush. If you go west into VT spend a night in either Southern VT, maybe Woodstock/Killington area, or the Lake Sunapee area in NH. Basically stick close to I-89. Then, drive back to Boston for the flight home.

Personally I'd end my trip in Burlington and fly out of there instead of driving back to Boston but it'll probably be a lot easier to fly and rent a car out if the same airport.


Tigre85
Houston Astros Fan
Louisiana
Member since Feb 2019
1114 posts

re: Need Help Planning 7 Day Road trip to New England
Do yourself a huge favor and listen to abitafan . He was spot on for our trip 3 years ago ...


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