A 9-Day East Coast of America Road Trip: Travel Route

In July this year, my boyfriend and I embarked on a road trip across the East Coast of America.

After a quick 36 hours in New York City, we picked up our rental car and headed on our way. Our first stop was the Hamptons, then Providence, Boston, Cape Cod, Salem, Portland, Bar Harbor, Burlington, New Haven and then back to New York City for our flight home.

All in all we ticked off six states: New York, Rhode Island, Massachusetts, Maine, Vermont and Connecticut.

It was a lot of driving and a lot of sightseeing, amazing food and completely contrasting parts of America. I loved every minute of it and can’t wait for our next road trip across America.

Related blog posts to read:

Top tip: for mobile data around America, we used the Airalo eSim. This was super handy and easily installed onto our phones as soon as we landed in New York!

Below is my first YouTube video of the road trip. I’ve also added in vlogs from the other areas we visited, further down this post.

Table of Contents

Day 1-3: New York City

We arrived into New York City around 5pm on a Friday evening and it was hot. We grabbed our first Dunkin Donuts of the trip and walked along the west side of Manhattan. From TriBeCa down to Battery Park to see the Statue of Liberty.

We picked up dumplings from our favourite dumplings spot and walked around some more. Then grabbed a light dinner at one of our favourite restaurants, the Himalayan Cafe. It was then back to bed where we were staying at the Sheraton, TriBeCa, somewhere we’ve stayed previously before.

Our only full day in New York on the Saturday was an exciting one. We started off with breakfast at our favourite, Two Hands in TriBeCa. Then headed to Soho so I could finally get my hands on a bottle of the Glossier You fragrance.

It was then time to hunt for a tattoo shop and get my first ever tattoo!

After this it was insanely humid, so we stopped at Down the Hatch for a drink. Followed this with a slice of Joe’s Pizza and headed to Washington Square Park. Grabbed a Levain Cookie, walked north through Manhattan, and stopped at The Strand bookstore. Then it was on towards Central Park to nap in the shade for a while until it cooled down.

For dinner we headed to another favourite spot, Malatesta Trattoria in the West Village. The perfect spot for beautiful Italian food before calling it a night again.

On Sunday we were up bright and early to collect our rental car near JFK and begin our road trip!

Day 3-4: The Hamptons & Providence, Rhode Island

The first part of our road trip was to drive through the Hamptons. Himself had never been before, but I had spent a Thanksgiving in Sag Harbor a few years ago.

So it was going to be nice to revisit the place again.

The Hamptons, New York

We stopped first in Southampton and had lunch at Sip ‘N Soda Diner and explored Main Street. It was then onto East Hampton for more wandering. Before finishing in Sag Harbor to wander their streets some more. Finally, we made our way to the ferries that would take us across to New London, Connecticut.

One thing I will say about the Hamptons is that the areas are quite similar. They mostly have similar stores, shops and one Main Street but a lot of nice restaurants. It’s somewhere I’d like to revisit in the future, but to stay somewhere for the weekend and enjoy the beaches.

We had to take three separate car ferries to make it across from Sag Harbor, NY to New London, Connecticut.

The first was from South Ferry to Shelter Island (5 minutes). Then we drove through Shelter Island to North Ferry which took us to Greenport (10 minutes). It was then onto the final ferry from Cross Sound Ferry to New London, Connecticut (1 hour).

The first two ferries were cash-only and the queues to get on were quick, and they came every 5-10 minutes. The final ferry we had to book in advance, online. If you turn up earlier than your booked slot, be prepared to wait an hour or more. If you’re really early, they’ll put you on standby until they have space for you.

Providence, Rhode Island

Once we arrived in New London, it was an hour drive to our final stop of the day Providence, Rhode Island.

We checked into our hotel and grabbed some food and were very surprised at just how empty Providence was. It was like a ghost town and felt quite eery at nighttime. But we had an incredible meal at Wok & Pot which was a great way to end the first day of our road trip.

The next morning we woke up and headed out to explore Providence before we had to be on the road. We visited Brown University campus and I tried to imagine Serena Van Der Woodsen being a student there. For the number of Ivy Leagues I’ve visited, Princeton is still my favourite.

Day 4-6: Cape Cod, Boston & Salem, Massachusetts

Provincetown, Cape Cod, Massachusetts

From Providence, Rhode Island, we made our way to Provincetown, Massachusetts on Cape Cod. This is said to be one of the gayest towns in America! It was a gorgeous seaside area of Cape Cod with lots of shops, tourists and holidaymakers.

We had our first taste of Massachusetts lobster and clam chowder from The Lobster Pot and it was incredible. We went on to have so much lobster that I haven’t been able to look at one since.

P’town was definitely worth a visit with lots of art stores, fun alleyways and felt like another world completely after leaving Providence.

Boston, Massachusetts

Then it was on to Boston, and I was so excited to come back here. This was the first ever road trip my boyfriend and I took when we lived in New York. We checked into our hotel which had amazing views of the city. Then headed to the North End (Little Italy) for dinner in the same restaurant we dined in years ago: Giacomo’s.

This was a very popular spot with a queue down the street to get in, but so worth it.

The next day we had a full day in the city and it was another scorcher of a day. We grabbed a hearty breakfast at The Friendly Toast. Afterwards walking the feet off of ourselves along the Freedom Trail and into Faneuil Market for some more clam chowder.

That night, we were heading to watch the Red Sox play at Fenway Park. It started to rain when we arrived which was the first bit of rain we’d had on our trip so far. Play was delayed for a while but it was fun to get some drinks and spend the evening watching baseball.

The next morning it was time to check out and grab some last minute cannolis for breakfast from the North End. Then making our way to Salem before driving onwards to Portland, Maine.

Salem, Massachusetts

If you’ve been around for a few years, then you’ll know that Salem was always very high on my USA bucket list and I got the chance to visit when I lived in New York, during our first visit to Boston.

I had been itching to go back and see some things that we had actually missed the first time, especially made easier now that we had a car. We walked around the usual spots to see including the Witch House and Main Street, but I was most interested in doing a tour of the Hocus Pocus filming locations.

This time, we seen Max and Dani’s house, the Pilgrim village where they film the opening scenes, and Allison’s mansion.

I love Salem and can’t wait for the day I can go back in the autumn-time when it will be the real witchy-season and make time for some walking or witch tours. Another road trip awaits!

DAY 6-8: Portland and Bar Harbor, Maine

From Salem, it was then on to the state of Maine where our first stop was Portland. We only had a few hours that evening to explore the area, try even more lobster and see as much as we could before having to take off early the next morning to Bar Harbor.

Portland, Maine

We were staying a little outside the city so made use of Uber to get to and from our hotel. We walked around the quaint streets of Portland, stopping in Sherman’s Bookstore and picking up a book by Nora Roberts that was set in Maine.

Fun fact, did you know Stephen King is from Maine? They had a section dedicated to him in most bookstores we visited in both Portland and Bar Harbor.

For dinner, we headed to Luke’s Lobster on the water and the area was very much giving every summer romance novel I’ve read that’s been set in New England. We shared an excellent lobster roll and it was lovely to sit out on the water and enjoy the sun going down with a cocktail.

After this, we moved on to the famous Duckfat for their poutine. It’s a very small but very busy location but was well worth waiting for a while. We sat at the bar area and loved the staff here as well as the food.

After walking this off for a little while, we went to The Highroller Lobster Co. for some oysters to wash everything down. This was a really cool diner that had been highly recommended, and is somewhere I’d visit again if I ever find myself back in Portland.

Bar Harbor, Maine

The next morning we headed off early for our long drive to Bar Harbor. The weather took a little bit of a turn on this day, and we made a few stops along the way to Bar Harbor to break up the drive.

We stopped at a very large antiques store for a wander around the many floors and rooms of random things for sale. We soon noticed that there are a lot of ‘antique’ stores along the US highways and I’m not sure if you’ll find anything worth buying, but it is worth stretching your legs and having a walk around.

Then we stopped at a roadside shack for some clam chowder which we can’t get enough of. The rain started to come down heavily at this point, so we kept going until we reached our B&B.

We were staying at a very cute house very close to the main street of Bar Harbor, which had two dogs and some other couples staying there. It was my first ever time staying in a B&B and I loved it.

We checked in and then headed on a drive around Acadia National Park and take in the amazing scenery. The rain had dried up but it was dark and made the park seem quite eerie.

For dinner, we drove out to another famous lobster shack about fifteen minutes away. We had more lobster and more clam chowder, and finished with some blueberry pie which Maine is apparently quite famous for.

When we came back, there was still a storm warning so we headed for a drink in the local Irish bar which actually happened to be the closest Irish bar to Ireland in all of the US, so that was quite fun.

Whale watching

We had booked whale watching for the next morning, so had to be up at the crack of dawn to make it.

At 6.30am we made our way down to the harbour and it was a stunning day. But when we arrived to the boat we learnt that the whale watching was cancelled due to the previous day’s bad weather with too much fog still lingering and 4ft waves which would not be pleasant for those who are prone to seasickness.

That was probably the most disappointing part of our road trip as we’d really been looking forward to doing some whale watching, but you can never plan the weather and it just means we’ll have to book it again sometime in the future.

With no whale watching to do, and it being 7am, we headed for an early breakfast at the famous Jordan’s Restaurant. I had a bowl of fruit and yoghurt with a side of blueberry muffin.

Since it was such a gorgeous day, we took the opportunity to take another drive around Acadia National Park and see it in all its beautiful glory minus the grey skies and wet roads and it really was beautiful.

Then we were on our way to Vermont early which worked out quite well for us since it was a seven hour drive to get there.

DAY 8-9: Burlington, Vermont & New Haven, Connecticut

Many Dunkin Donuts were consumed during our seven hour drive to Vermont and unfortunately not one moose was seen on the road.

Ben & Jerry’s Factory

We made a pit stop on our way into Burlington by stopping at the Ben & Jerry’s Factory and seeing the famous flavour graveyard. It was definitely worth stopping by to see the flavour graveyard at least as this was free, and you can pop into the gift store too.

Burlington, Vermont

We finally made it to Burlington and found our AirBnB, although it was probably our creepiest/strangest stay of the entire trip.

We made our way into the centre of Burlington and found a Nepalese spot for food so had some momos and noodles, before heading down to the water to catch the sunset.

Down by the water was definitely my favourite area of the city, and there was a festival happening along the pier so we sat for a while and enjoyed the music while watching the sunset, and also savouring the moments of our final night on the road trip.

I will say that we probably wouldn’t rush back to Burlington as it didn’t feel like the safest place we had visited on our trip and they seemed to have a very big homeless problem too.

The drive to and from Burlington, Vermont was probably our favourite and most scenic with the mountains and trees lining the highways.

New Haven, Connecticut

The next morning we left around 10am to make our way back to New York for our flight at 11pm.

We stopped in New Haven, Connecticut for an hour or two to visit another state and try some of Sal’s famous pizza. We walked around the city in the very hot weather which was surprisingly very quiet.

Afterwards, we picked up our pizza and took it to Yale University and ate on the grass here to enjoy our last meal of the trip before having to make the final drive back to New York.

Hometime

We arrived at JFK Airport and handed back our rental car (in the torrential rain which you’ll see in my YouTube vlog), and then made our way to our flight back to London.

Thankfully the driving aspect of our road trip went smoothly the entire time and I would plan another road trip across America again in a heartbeat.

I think a road trip or visiting more than one place in one holiday is definitely the way I love to travel most.

I’ll be updating this blog post with each of my YouTube vlogs once they’re published, and also writing smaller dedicated blog posts for each area that we visited soon, so make sure to come back to this post to see the latest updates.

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Day 1-3: New York City