New England Road Trip: my step-by-step itinerary

New England Road Trip

Our 2015 summer trip was really a last minute one and so I couldn’t organize it very well like I usually do (and like).
Anyway, with just an e-book guide by our side and relying on Wi-Fi connections to check Airbnb rooms to stay while on the go, we were ready for a new adventure!

New England Road Trip:

my step-by-step itinerary for an exciting journey of 15 days

We couldn’t buy a plane ticket well in advance because of work obligations, so what did we do? We used a very useful mode on the Skyscanner website: the “everywhere” destination. After some brainstorming, we thought that the best value for money was New York City! We have already visited it (not that we wouldn’t have liked to see it again) but I immediately had the idea of doing an East Coast / New England trip!
At the end, we bought the plane tickets on Kayak, as we couldn’t use our credit cards on the websites provided by Skyscanner after many frustrating tries 🙁
Well, August has come and so the time of our holidays.
We landed at midday in JFK airport and made our way to the bus stop of the Megabus company in Manhattan (not an easy task…but that’s another story).

New England Road Trip
Welcome to New York!

We have decided to begin our trip in Boston and to take the car after our 3-day stay. Public transportation is good in the city so you won’t need a car. Besides, parking prices are very expensive.
We used the Wanderu website to know which company and which time were the best for us. Wanderu is a great service designed to find and book bus and train tickets to travel in North America. So happy I have found such a good website, it would be nice to have a similar service in Europe!
We didn’t try trains as they were all very expensive, but we can really recommend using buses to go to major cities as they are really cheap, comfortable and reliable…no complains whatsoever!

After a very pleasant journey, we arrived in Boston and we went by subway to our Airbnb host (we have previously booked this first room at home). The area is called Brookline and it’s a really nice and safe neighborhood. I can highly recommend it as it’s surely cheaper than the city center (room prices are steep!) but it’s still very easy to reach everything in Boston by public transportation. There are also nice places nearby to eat and drink…we had a good first dinner here (although it was really too expensive).

BOSTON day 1
We decided to begin our visit going to Harvard University with its huge buildings and lively Cambridge Square (Red Line: Harvard Square St.) before walking to the outstanding MIT (Massachusetts Institute of Technology).
Well, instead of going straight to MIT we went to the opposite way for nearly 30 minutes…but that’s just because we love to walk, right?
On our way to nowhere we accidentally stumbled upon a backyard party so it wasn’t bad after all 😀
The area of MIT is full of amazing architecture such as the Stata Center, an academic complex designed by the great architect Frank Gehry, and a great waterfront overlooking central Boston.

New England Road Trip
Stata Center by Frank Gehry

BOSTON day 2
Next day the sun was shining and we have decided to join the “Free Tour by Foot” (meeting was at 10.30 at Park Street St.).
Every time I go to a city, I check if there is a free tour…I think it’s ideal to go to tours where passionate people lead you around and then, at the end of the walk, you tip them based on what you feel it’s right.

New England Road Trip
Massachusetts State House

Our Boston tour guide was knowledgeable and witty…we followed him explaining the history of the first monuments on the Freedom Trail (it’s a 4 km path leading to 16 locations significant to the history of the US), until we arrived near the Faneuil Hall. He left us there and we went inside it to eat at the Quincy Market.
That place is definitely a must go for food lovers although it can be expensive (looks like a Boston pattern here).
Afterwards we checked by ourselves the remaining monuments on the Freedom Trail until the last ones: the Bunker Hill Monument and the USS Constitution.

New England Road Trip
Bunker Hill Monument

There are also many other walking tours of course, but we were happy with the one we chose.
Going back, we explored also North End, the Italian American neighborhood. I was skeptical about it as always regarding so-called Italian places abroad, but I have to admit that, in this case, it was a very nice area to walk.

New England Road Trip
North End…the Italian American neighborhood

We were then going back to the center when, near Quincy Market, we stumbled upon the New England Holocaust Memorial…six tall illuminated towers and perpetual smoke from the ground bring terrible past alive. It was really touching; we were lucky to have found it by chance. It’s a simple structure depicting a very strong message.

New England Road Trip
New England Holocaust Memorial

Before going home, we concluded the day at Falafel King (260 Washington Street), eating falafel like there was no tomorrow. No frills place, but very good food (not only falafel)! They even give you a falafel for free while waiting for your order to arrive!

BOSTON day 3
On our last day in Boston, it was unfortunately raining a lot, but we had one important thing to do, to pay homage to a great invention of humankind: beer! We went to visit the “Samuel Adams Brewery”. You will find it easily after getting out at Stony Brook St. on the Orange Line. The tour is completely FREE of charge and it has amazing beer samples at the end! What else would you want if you are a beer lover like us?

New England Road Trip
Samuel Adams Brewery

We then went to visit Copley Square with its beautiful churches (the oldest one being Trinity Church) and to have a light lunch in Newbury Street, a road famous for high-end shops and restaurants.

New England Road Trip
Copley Square

The area is very nice, it has many historical houses and it’s great to have a relaxing stroll around looking at them. You can also visit the waterfront park…it’s easy to reach with interesting pedestrian bridges crossing high speed roads and it’s really wide and full of things to do.
Unfortunately for us, it was still raining and so we didn’t stay long.
Afterwards, we explored Chinatown and found it very interesting with its little shops, Chinese signs and the colorful gate…it was soon dinnertime and we found a cool Malaysian restaurant. We ate so well and cheap (gorgeous big bowls of noodles) that Malaysia is now high on our bucket list!

BOSTON – SCARBOROUGH (near Portland)
It was time to leave beautiful Boston and so we went to Alamo, the rental car company we have chosen, to take the car we have already booked online and to begin our New England road trip!
Our first stop was Salem (only 15 km from Boston) and I really loved its quiet roads and quirky shops. Salem is famous for the witch trials in 1692 – 1693 and there are witchcraft shops and museums everywhere you look.
One can think it’s only marketing, just a way to sell goods, but nevertheless I felt something magical hidden behind the cheesy stuff.

New England Road Trip
Amazing installation in Salem

After eating something quick, we head to Gloucester, Cape Ann in Rockport, Plum Cove Beach and Portsmouth…parking when we could and taking many pictures at the wonderful coastline.

New England Road Trip
The amazing Maine coast

In Portsmouth, we parked longer and had dinner in a nice place, the “British Beer Co.” with good beers.
We arrived late in the evening in our new Airbnb house and fell soon asleep after a good tea and some nice talks with our host.

SCARBOROUGH (near Portland) – OLD TOWN (near Bangor)
We kept driving up north on the Maine coast and the first place we stopped for a while was the famous Cape Neddick “Nubble” Lighthouse (York Beach): amazing coves and bays dominated by an impressive lighthouse.

New England Road Trip
Cape Neddick Lighthouse

We then had a walk and a quick lunch in the college town of Brunswick (the guide suggests to stop here but, to be honest, there’s not so much to see; it was still a quiet and peaceful place).
A town you should visit for real is Wiscasset, called the “Prettiest Village in Maine” and it’s not a lie. It’s really tiny and with perfect homes on a river with a long bridge taking you to Boothbay Harbor.

New England Road Trip
Wiscasset bridge to Boothbay Harbor

This is another perfect Maine village…bigger and livelier than the previous one; it has many restaurants and several opportunities of taking a boat and do ocean tours of various distances and lengths. We would have loved to go whale watching (Maine is the perfect spot during summer), but unfortunately we didn’t have time 🙁

New England Road Trip
Boothbay Harbor port

We arrived quite late also today at our new Airbnb room and we panicked for a while as there was no one inside the house but, after a while, our host arrived, telling us the door was open! From now on, we came to understand the majority of people doesn’t close their house door!

OLD TOWN (near Bangor)
The day after we headed to Acadia National Park. It’s located on Mount Desert Island and some surrounding smaller islands close to Maine / Canada border.

New England Road Trip
Acadia National Park from above…

You have to pay 20$ per car in order to do the Loop, an established road all around the main East area that follows the best stops to see. Before going that way, we also visited the Western part thanks to the tips of our hosts. That’s why I love Airbnb: you get to talk with real people and exchange stories, ideas and places to see!

New England Road Trip
One of the many gorgeous stops…

Thanks to them, we also ate our lunch at Thurston’s Lobster Pound in Bass Harbor, a great place right on the ocean. Rustic look, delicious food and amazing views: highly recommended!

New England Road Trip
The view from Cadillac Mountain

OLD TOWN (near Bangor) – BETHEL
We left our great two nights hosts and began going back south.
We should have gone inward (visiting another historical town) but we preferred visiting the Maine coast towns we should have seen before, but didn’t have the time to do. Time was running fast!
First stop was beautiful Camden with its quirky little shops (we bought some souvenirs here…like a giant lobster mug 😀 ).

New England road trip

We then passed through Rockport with a laid-back atmosphere and parked in Rockland where there was the “Maine Boats, Homes & Harbors Show”.
Without knowing it, we have found a boat event with many business pavilions and interesting food trucks. We were looking around trying to get what was going on, reading the entrance price was 12 $, thinking it was too much as we are not really into boats, when the women at the entrance gate gave us admission wristbands for FREE…thank you, kind souls!

New England road trip
Rockland boats show

We wandered around the beautiful waterfront and ate very good tacos at the “Fox on the Run” food truck. Sitting at a wooden table, a man began talking with us and we had a very long and interesting conversation with him about our lives. I love talking with locals!
We then said our goodbyes and headed to the stunning Owls Head Lighthouse…following a short and easy path in a wood, you will find it on a pointing cliff out in the blue ocean. To get to the lighthouse itself, you have to climb a steep staircase, but the view is worth the effort.
Pemaquid Point Lighthouse was our last and maybe best stop; we loved wandered around the rocks and perceiving the ocean…a relaxing end of our day.

New England Road Trip
Pemaquid Point Lighthouse

There was also a very nice guard who let us enter free of charge as it was closing soon…thank you, kind soul!
We then arrived at our new Airbnb host in the woods of Bethel, a romantic village in the mountains.
Thanks to her tip, we had a perfect dinner in a great place in town: the Mill Hill Inn. Unbelievably good “tapas style” food!

From Bethel we moved inward and took the scenic road n° 16 to get to Conway area.
North Conway is the place to go outlet shopping (although we didn’t) but this area (Albany in New Hampshire included) is famous because you will find many covered bridges…made of wood, they were covered to protect the fragile structure from the weather. I read that once upon a time there were 12.000 in the United States…now they are of course way less. I really liked to walk under their old roof looking at the river and thinking about the people who walked the same paths so many years ago.

New England road trip
One of many covered bridges

We then passed through the White Mountain Park. Inside, there is Mount Washington to visit too (you can climb it, go by your own car -beware of the very steep road- or by a train or bus tour), but as it was very expensive and we didn’t have so much time, we decided to skip it and just see it from below.
Our next Airbnb room was in Newbury, Vermont and it was really like a home away from home…so many dogs and cats (and two horses) made me feel like I was in paradise!

Thanks to our hosts tip, we went to Stowe to see the Trapp Family Lodge, the beautiful Austrian style resort built by the family who inspired the film “The Sound of Music”. They built it here as the mountains view made them think about their motherland.
It was really a nice surprise, as I’ve always loved this movie!

New England Road Trip
The Sound of Music lodge

After a good meal in the nearby town of Northfield, we went to visit a great microbrewery: Magic Hat (5 Bartlett Bay Road, South Burlington).

Vermont is famous for its microbreweries and we really wanted to try at least one of them!
This place is great, full of bizarre and eccentric stuff; there are guided and self-guided free tours of the factory (no reservations needed) and some friendly bartenders will give you 4 delicious little samples of the week’s tap. Another great way to enjoy some time with the magic liquid. 😀

New England Road Trip
Magic Hat brewery

We then visited one beautiful city: Burlington. The largest city of Vermont is a college town and you can feel its young vibe.
I loved the lively pedestrian main street, the different restaurants and most of all the beautiful Lake Champlain and its stylish waterfront! It was so peaceful and relaxing to watch the amazing sunset from beautiful swing benches…

New England Road Trip
Burlington sunset

NEW HAVEN – CLARKSBURG (near North Adams)
After a good night sleep, we headed to Middlebury, a town known for marble works; we walked around relaxing in its parks on the river.

New England Road Trip
Marble…rocks 😀

We then arrived in Bennington, an historical town known for its Battle Monument, the tallest structure of the state. We didn’t get up but I loved the big moose statue in front of it: painted with covered bridges and nature, it was the perfect selfie subject 😀

New England Road Trip
The Moose (no selfies for now)

We then had to leave green Vermont; it was time to go back to Massachusetts!
We headed to North Adams, a town known for the largest contemporary art museum in the United States: the Massachusetts Museum of Contemporary Art (MASS MoCA). Unfortunately, we didn’t have the time to visit it, but I surely recommend going inside if you like this kind of art.
Anyway, you can really feel the innovative spirit of the city as there are many art galleries and murals around and you can see old factories converted into lofts for creatives…as well as many lively restaurants full of people.

New England Road Trip
“Do you believe in unicorns?” …wall art in North Adams

CLARKSBURG (near North Adams) – BECKET
Leaving our North Adams suburb, we drove to visit Great Barrington, Stockbridge and Lee, three towns in Berkshire County.
The Berkshires (how the locals called it) is a beautiful area full of renowned nature beauties and cultural activities.
We then passed through Tyringham looking for Santarella, the gingerbread house. At the beginning, we couldn’t find it so we just drove on the main road back and forth for some time, but we finally saw it with a big sign I still don’t know how we couldn’t see it before.

New England Road Trip
The gingerbread house

Sir Henry Hudson Kitson, an English sculptor, began making this fairytale building around 1920 and worked on it for the last 25 years of his life.
You have to see it to believe its magic, although you can walk inside only if you book a romantic getaway or a wedding/event…do you have any ideas? I would love to attend your celebration 😛
Before going to our new Airbnb place, we passed through Lee and stopped at a little outlet shopping center, Lee Premium Outlets.
Plenty of parking and nice layout, but we didn’t find great bargains. The prices weren’t good, so we ended up buy nearly anything.
We had a bit of a struggle to find our new home hidden in the Sherwood Forest area of Becket (yes, for real! You should have seen the name of the roads!), but there we were, in a beautiful big residence. After a very nice conversation with our new hosts, we went to have dinner in a place they recommended to us (after getting lost in the woods).
Dream Away Lodge is a very nice restaurant up on a hill with a big garden and an open fire. The interior is cozy and there was a jam session band on the night we went. The food was very unusual (and good) but, at the end of the end, it was also too expensive for my tastes…in addition, the service wasn’t exceptional. Overpriced.

Another different New England state today: Connecticut!
Hartford is the capitol city of Connecticut and I must admit I’ve never heard about it before organizing this trip. Well, it surely was a nice surprise! It’s really a beautiful city with some gorgeous buildings and a very nice and modern waterfront (recently made).

New England Road Trip
Connecticut State Capitol in Hartford

There is a downside: exorbitant parking prices! Unfortunately, we didn’t think about checking the situation beforehand and so we ended up spending a fortune! I surely recommend checking if there are some low price parking places or if it’s better to park outside of the city and reach it with public transportation.

Mystic is a nice little village in Connecticut known for Mystic Pizza, the restaurant in the homonymous film with Julia Roberts. We didn’t eat there but we took some pictures of it and walked around the pleasant streets.

New England Road Trip
Mystic Pizza

After crossing a bridge (4 $ fee, but it’s worth it as you will save a lot of time plus it’s also a nice structure), we reached Newport… we were in Rhode Island!
The heat was nearly unbearable but we managed to do a part of the Cliff Walk, a nice 5 km coastal path where you can see many big and beautiful mansions.

New England Road Trip
Newport Cliff Walk

Park in Narraganset Road (Forty Steps section) because, going right, you will find the best part of the Walk. Beware you have to pay a small parking fee and so, if you are not American, you will need some coins because the machine doesn’t accept international credit cards.
Some nice girls gave us some coins, as we were short of cash…thank you, kind souls!
After eating in downtown Newport, we proceeded to Plymouth, the place where the Pilgrim Fathers first set foot on American soil.
We saw the Mayflower reproduction and the 1620 stone said to have welcome the Pilgrims.

New England Road Trip
Pilgrim Fathers Stone

We wandered around before arriving to Weymouth, a town south of Boston where we have found a cheap room to sleep in before going to the big city the next morning.

This was our last day on New England soil…we drove to central Boston and left our car at the Alamo parking. Then we walked few blocks to the South Station. This time our bus for NYC was from Bolt bus company, but also in this case the ride was very smooth (although the Wi-Fi wasn’t working) and we arrived in Manhattan on late afternoon.
We reached our Airbnb host walking a bit through those well-known roads. We have found a great room right in the middle of the action: near Times Square and the Empire State Building!

New England Road Trip
Stunning view of the Empire State Building

Shortly afterwards we left or luggage and walked again around looking for a place to eat.
Easy task in New York City as it’s a food lover mecca! We really wanted to eat ramen so we looked for some Japanese restaurant and found one we liked nearby; it’s called Azuki and a Naruto drawing picked my attention.
My bf ate ramen, but I ended up eating veggie noodles; both were really good anyway. We then spent our last night in the US walking in the lively streets, gazing at lights and soaking everything happening around.

Last day of our trip! We headed to Central Park. Last time we were here, it was winter, so it was too cold to wander around. This was our new chance to enjoy the greenery, see the squirrels and just relax on some benches.

New England Road Trip
Central Park

Going back south, we went to Bryant Park, a little gem I loved in winter and found lovely in warm weather.
TRAVELLING METALHEAD FUN FACT: we saw a protest on the streets about “nipples”! It was really interesting to get past their weird appearance (everyone was bare-chested and men had funny bras and writings on their skin) and understand the deep meaning of their march: to free women nipples from their sexual connotation like men ones, a goal for gender equality.

New England Road Trip
Walking past the Rockfeller Center

It was lunchtime and so we went into a stylish place we didn’t see the other time (maybe it’s new)…it’s on the Seventh Avenue near Times Square and it’s called Wasabi – Sushi & Bento. The cool concept is there are many different types of box sets (bento) you can choose. There is also hot food you can order at the desk. You can then take the food away or you can eat at some tables.
We ate two delicious and very cheap box sets sitting at the window and people watching 🙂
Last thing we visited before taking the tube to JFK airport was the High Line, a place I always enjoy going to and probably one of my favorite part of the city. It is an abandoned railway track turned into a pathway with gardens, benches, flowers…it’s so lovely to walk into nature among skyscrapers.

New England Road Trip
The High Line

Maine coast and its lighthouses
Burlington (Vermont)
Hartford (Connecticut)
Unexpected acts of kindness from strangers kind souls

No time to go whale watching 🙁
Not a cheap destination so we had to struggle a bit to stay within our budget (Boston was particularly expensive)

The New England road trip was very different from the West Coast one we did in 2013 (it was probably more European in some way) but it was a great adventure. We could experience a new area of the States and understand once more how varied this country is.

12 Replies to “New England Road Trip: my step-by-step itinerary”

  1. I came across your blog while researching for our New England road trip in May. We are going on a similar itinerary but staying for about 8-9 days. You mentioned that took the Megabus, travelling from JFK to NYC. Can you give me some tips? We plan to do the same thing as we land in JFK. We are also going to pick up and return our rental car in Boston.

    1. hm_metalqueen says: Reply

      Hello Rowena,
      thanks for your comment!
      From JFK you have to take the Airtrain, a light train connecting terminals (for free) and a NYC subway stop (you pay once you get out: $5).
      Then you have to pay the ticket to ride the subway in order to reach the Manhattan address where the Megabus stop is located. For us, it was quite difficult because there were some works going on and so we could take the subway for very few stops and then we had to wait for a bus for ages as every bus coming was always full…well, just some adventures to tell 🙂
      But I’m sure you won’t have this problem and you’ll be able to reach the address much more easier than us!
      Anyway I highly recommend using the bus to arrive in Boston and then take the rental car after visiting the city.
      If you have any other question, please tell me.
      Have a great trip!

  2. Rhonda Gammon says: Reply

    Hi, enjoyed your New England blog…we plan to do something similar at the end of September. We will probably do a loop, by the way..starting in Boston (with no car for a day or so), make a loop of the New England States, but especially are wanting to spend time in Maine/Maine coast and New Hampshire. We are thinking about 2 weeks; do you think that is a good amount of time to see the “high lights”? It may sound bad, but we’re not that much into history/museums, but more the lighthouses, the coast/beaches, landscapes, mountains; any good scenery. I have to put together a good itinerary soon, as I know the hotels will fill up early. Any suggestions, I would be grateful for!?!

    1. hm_metalqueen says: Reply

      Hi Rhonda,
      thanks for stopping by!
      I think that 2 weeks are a good amount of days to see the most important things…we had the same time and didn’t feel rushed at all although we missed the opportunity of going whale watching (but I’m sure it’s our fault aka “wasting time somewhere”).
      September must be lovely for the autumn tree leaves and of course this could mean more people and less free places. I suggest you look into Airbnb as we found very nice homes to stay in.
      If you have any other specific questions, please let me know!
      Enjoy your trip, it will be amazing 🙂

  3. what a refreshing article it is..i really liked your all pictures but The view from Cadillac Mountain and Burlington sunset are have done justice to these places i must say..seems like heaven on earth

    1. hm_metalqueen says: Reply

      Thanks a lot, Albert!
      Those places are really heavenly 🙂

  4. Thanks for all this info! Will come in handy for planning my own trip.

    1. hm_metalqueen says: Reply

      Hello Rania,
      thanks to you for your comment 🙂
      Enjoy your trip!

  5. Hi, your trip sounds great and I will definitely adopt some of your ideas, several of them even!

    The only thing missing here for me is a map of your route, which would help give some additional perspective about how you traveled.

    Thanks for sharing.

    1. hm_metalqueen says: Reply

      Thanks a lot, Cindy, for your kind words! I’m glad you find the post useful 🙂
      And thanks for your advice, I will add a map as you suggested.
      Have a great trip!

  6. bob killion says: Reply

    My wife and I are planning to go to New England in August or September. Just started surfing the web and saw your article. Thank you so much for doing this.
    If you were going to stay in one place and take day trips any suggestions?
    The world would be better with more people like you who take the time to help others.

    1. hm_metalqueen says: Reply

      Dear Bob,
      I’m so sorry I didn’t see your message. I hope that your trip went well and that my itinerary was useful.
      Probably the area of Bangor is the ideal place to stay for a while, but I’m sure you chose well.
      Thanks a lot for your nice words.
      Take care

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