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New England Road Trip: Start in NYC or Boston?

New England Road Trip: Start in NYC or Boston?

Old Mar 28th, 2018, 12:16 PM
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Join Date: Mar 2018
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New England Road Trip: Start in NYC or Boston?

Hello! I'm sure this has been talked about many of times over, but I was hoping to get some first-hand answers before I make a decision.

My boyfriend and I were looking to do a New England road trip up to Acadia State Park, but starting either in Boston or NYC. The only reason we are looking at NYC is that it would give us 1 day there and we would pass through New Haven to grab some iconic pizza. We are looking at going May 24 - May 30, flying into either Boston or NYC the evening of May 23 and flying out of Portland, ME on May 30 back to Atlanta. Given the 1 week timeframe, should we just stick with Boston?

We are a couple, mainly interested in good food and scenery. Hiking/sailing is fun. Like arts and culture, but definitely don't like the usual touristy things. I'm interested in seeing moose and puffins in Maine, as well as the coastline and some lighthouses.

Here was my *initial* thought on flying into NYC:
Wed night: Fly into NYC
Thursday: NYC
Friday: Rent car, drive up to New Haven (2.5 hours)
End up in Boston (2 hours)
Saturday: Boston
Sunday: Salem/Portsmouth/Portland, ME
Monday: Camden/Acadia
Tuesday: Acadia
Wednesday: Drive back to Portland (2-3 hours) fly home evening

Flying into Boston would of course allow more time to leisurely explore the coast.

Any suggestions on which way to go? Also, suggestions on must see/must eat/and things to skip?
ogmartabus is offline  
Old Mar 28th, 2018, 01:12 PM
Join Date: Mar 2003
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I would start the trip in Boston, but if starting it in NYC, you might be interested in the historic ships in Mystic--https://www.tripadvisor.com/Tourism-g33845-Mystic_Connecticut-Vacations.html
Michael is offline  
Old Mar 28th, 2018, 02:15 PM
Join Date: Sep 2007
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I'd start the trip in Boston. While New Haven has a way with "apizza" as they call it, I'm sure you would be more than satisfied by Regina Pizza at 11 1/2 Thacher Street in Boston's North End. Stick with the simpler traditional toppings for the best flavor. Be prepared to stand in line a while, though.

Last edited by Fra_Diavolo; Mar 28th, 2018 at 02:37 PM.
Fra_Diavolo is online now  
Old Mar 28th, 2018, 02:30 PM
Join Date: Dec 2008
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If you care about money, you might want to look at the cost of dropping the car at a site that you didn't get it from.

You could fly into NYC spend the night in NYC, take the train to New Haven, get the pizza then head to Boston on the train. Rent the car when you leave Boston to see Salem etc.. I'm thrifty enough to drive back to Boston and fly out of there to avoid the drop fee and probably BOS>ATL will be a less expensive leg than from Portland.
emalloy is offline  
Old Mar 28th, 2018, 07:12 PM
Join Date: Nov 2013
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I too would skip nyc and new haven and fly in and out of Boston. Checking out Santarpose and Reginas in NE. Frankly traveling thru New Haven will be a pricy slice of pizza. Chestnut Hill In Boston is a treck but opened a Frank pepez pizza - I haven't beeb,

That will give you more time to see and feel the vibe of Maine and northern MA. Unless you want a drive by vacation.
Inakauaidavidababy is online now  
Old Mar 28th, 2018, 08:06 PM
Join Date: Nov 2010
Posts: 10,596
Fly to Boston. Rent a car for 1 day to see things within a couple hours drive of Boston. Return the car in Boston and then take the Amtrak Downeaster to Portland from the Boston North station. Rent another car in Portland for all that you want to see in Maine. Return the car where you rented it and fly home from Portland. New Haven is much too far to go for a pizza.
tomfuller is online now  
Old Mar 29th, 2018, 03:56 AM
Join Date: Jan 2003
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tomfuller makes a great suggestion. You can also get bus service from South Station which is an easy link from Logan. The buses pick you up at Logan and then stop at South Station where you can buy tickets. But, if you plan to spend some time in Boston you can either take a taxi or use the mass transit system. The silver line picks up at Logan. Boston's North End would be a great place for pizza.

Portsmouth NH is a wonderful stop. Take a boat ride. Explore Market Square. Eat at one of the restaurants that share a deck that looks out on the harbor. Hippo is a free weekly newspaper that covers activities in the Portsmouth area as well as Concord, Manchester and Nashua. See their website.

Because Portland has been affordable, there's a lot of great restaurants and start-ups. I have not been to the Portland Museum of Art but loved the Farnsworth in Rockland ME. You are missing a lot of Maine by jumping from Portland to Camden to Acadia. Start by looking into where you can go for puffins. It will require a boat ride. You probably won't see a moose in Maine. There are areas where seeing one is likely but it's more inland and woodsy. You could do a loop to that area or NH's White Mountains and then back to Portland. Check out this link https://visitmaine.com/things-to-do/...moose-watching Best times during the summer are dusk or dawn. You would have to plan an overnight.

Camden is beautiful, especially the view from Mt Battie overlooking the harbor but it's also where all the tourists go who didn't stop in Ogunquit or Kennebunk. If you get a map of lighthouses you can find some interesting stops where you might be the only people. Pemaquid is very popular but there are others. We like to set up bag chairs and sit awhile with binoculars, snack and books. I suggest you google a list of Maine's lighthouses. It's fun to do a boat tour of lighthouses. The one we liked best was an all day trip from the Maritime Museum in Bath. They no longer do all day trips but a half day would be great, too. A boat ride out to Monhegan Island would give you hiking as well as a lighthouse visit. Take a picnic lunch.

Unfortunately, your trip in late May might be before some of the boat tours really get going. There's a lot you can do and you only have a week. Check hiking conditions in Acadia. A friend says they don't have black flies and she lives in Bar Harbor. We usually don't visit Maine until mid-June or later. Do not be put off by claims that Maine is too crowded during the summer. It's only crowded in the popular tourist areas. I tend to like 4th of July week. Bath has a great parade and Heritage Days. In May it will be cold out on the ocean so bring warm jackets.
dfrostnh is offline  
Old Mar 29th, 2018, 06:56 AM
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Thank you all for the insight. Looks like my best bet will definitely be flying into Boston. I even found flights from Bar Harbor back to Atlanta for $50 so I won't have to drive back down to Portland. I'm not worried about the car rental, picking up in Boston and dropping off in Maine will still only be $130 total for the week!

I had a feeling late May will still be a little chilly but I'm ok with that. 4th of July is already pretty booked and flights/car rentals will be much more expensive.

I like tomfuller's suggestion and I will definitely look into that as an option too. After posting I realized I probably wasn't going to see moose, but that's ok. dfrostnh thank you for your suggestion as well. I definitely don't want to skip over a lot of Maine, I was kind of generalizing. Flying into Boston will give us extra time to drive around for sure.
ogmartabus is offline  
Old Mar 29th, 2018, 08:29 AM
Join Date: Nov 2010
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The Downeaster goes all the way to Brunswick. If you ride to Freeport, you can walk to the L.L. Bean flagship store from the train station.
My wife and I were in southern Maine on May 23 last year. Several of the places we wanted to eat at were still closed for the season.
tomfuller is online now  
Old Mar 30th, 2018, 01:56 PM
Join Date: Jan 2003
Posts: 6,887
I would not bother with two car rentals and a train. What's the point? Driving in Maine is easy. Train and two car rentals will be more expensive, and time limiting. The train doesn't run all that frequently (maybe just once a day?). Fly into Boston, spend a day (for the pizza in the north end, not to mention the rest of the city). Rent a car and drive to Acadia (which is a National Park by the way). There's actually lots of good stuff between Portsmouth and Portland as well as between Portland and Camden.
isabel is offline  
Old Apr 1st, 2018, 03:01 PM
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Just a few things. May is black fly season in Maine, so keep that in mind and that is Memorial Day weekend, the official kick off for summer/boating season, you will encounter lots of traffic.
odie1 is offline  
Old Apr 15th, 2018, 06:33 PM
Join Date: Apr 2013
Posts: 489
Great deal on the flights from Bar Harbor! That will give you much more time to explore. Fly into Boston, check it out and then drive up the coast. Portsmouth and Portland are great small cities with awesome restaurants. You can't beat the Maine coast. York is very old school New England coast. Ogunquit has a walk called the Marginal Way which is beautiful if you have a nice day. We went up to Acadia the end of April last year and it was beautiful, no snow and in the sixties! You never know about the weather. We spent a night in Camden on the way and loved it! Boothbay is also a great place and things should be opening up when you go. In April many things were still closed. In Acadia you will find things open as we had no trouble finding restaurants in April. Make sure you stop and have popovers at the Jordan Pond House in the park. It opens May 14th so you are in luck! Acadia is one of my favorite places in the world. Have fun!
Sberg is offline  
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