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Classic Summer New England Road Trip

Classic Summer New England Road Trip
Rugged Coastline in Cape Elizabeth, Maine, on our New England Road Trip

A seafood lover’s take on the quintessential coastal New England road trip..

Growing up in New York City and attending school in Boston, I’ve developed great memories and quite an affinity to New England. I love the charm of the small cities, rugged shores of the Atlantic, cobblestone streets and delicious seafood fare.

Fast forward to today, it’s summer and I am currently living in Southern California, having deep craving for a lobster roll. It’s this craving that has inspired me to recollect my memories of this particular road trip I took after the pandemic. The itinerary of this trip will be quite food forward, since I wanted to try as many places and things on my bucket list as possible!

A New England itinerary could have many starting points, depending on where to live or fly in from. On this trip, we are kicking off the drive from my New York City home. I’ve previously started a road trip in Portland, Maine by flying in first and then getting a car at the airport.

I decided to finally do a summer road trip to hit up all the seafood shacks that were closed during the off season. It’s been on my bucket list for a long long time, already! A summer visit means a lot more tourists and higher travel/lodging prices, but it’s also the time with the best weather for eating lobster outdoors, hikes and beaches.

Previously, I’ve done a Fall Maine road trip and will be coming back for a New England winter road trip for my birthday! There’s something in the New England states for every season, whether it’s the spring blooms, fall foliage, summer lobster shacks, or winter slopes.

New England Road Trip Itinerary Summary

Starting Point

New York City

Cities Visited

New Haven, Connecticut
Narragansett, Rhode Island
Duxbury, Massachusetts
Portland, Maine
Cape Elizabeth, Maine
Kennebunk, Maine
Kennebunkport, Maine


Portland Harbor Hotel (Maine)

Dining Highlights

White Clam Pie at Frank Pepe Pizzeria (New Haven, CT)
Clam Cakes at Aunt Carrie’s (Narragansett, RI)
Raw Oysters at Island Creek Oyster Farm (Duxbury, MA)
Steamers & Lobster at Porthole Restaurant & Pub (Portland, ME)
Duck Poutine at Duckfat (Portland, ME)
Coffee & Doughnuts at The Holy Donut (Portland, ME)
Brown Butter Lobster Roll at Eventide (Portland, ME)
Steamed Lobster at the Lobster Shack at Two Lights (Cape Elizabeth, ME)
Fried Clam Strips at The Clam Shack (Kennebunk, ME)

Continue reading for all the details!

New England Road Trip From NYC

We are starting from New York City!

It has been on my bucket list to embark on a driving journey from NYC from start to finish. I wanted to experience all the stops and scenery along this coastal drive to Maine. Luckily, the drive from New York to Maine can be done within half a day including pit stops. It’s really a great trip that can be as short as you want or extended into weeks, depending on your time availability and wishlist. On this itinerary, we will make stops in Connecticut, New Hampshire, Massachusetts and then spend the rest of the time within Maine.

We used the Turo app to rent our car for this trip. It’s a peer-to-peer marketplace for cars. Think of it like Airbnb but for vehicles! You’ll be able to find some unique rides on here.

First Stop: Connecticut

Driving time: 1.5-2 hours

I feel like I take living close to Connecticut for granted. I’ve been up here for several occasions and reason, from tournaments at Yale to summer BBQs in Greenwich. It’s definitely a great state to explore if you have the time.

New Haven, CT

On this trip, we made our first stop in New Haven, CT, best known as the home of Yale University and the New Haven-style pizza. This Neapolitan offspring style of pizza is better known as apizza here. This city is know to be a destination for one of best pizzas here in the states thanks to the descendants Italian settlers around Wooster Square. You can enjoy the New Haven-style pizza without needing a trip to Naples.

A New Haven-style pizza is charred, thin crusted, crispy and not round. The most famous types pies are tomato pies and white clam pies. The best place to get it? It is hotly debated which pizza parlor serves the best pie, but from my research, you cannot go wrong with Frank Pepe Pizzeria Napoletana, Modern Apizza, or Sally’s Apizza.

Frank Pepe Pizzeria Napoletana

157 Wooster Street, New Haven, CT

New Haven Style Pizza: White Clam Pie at Pepe’s

I decided to go with the OG of the New Haven pizza, Frank Pepe Pizzeria Napoletana and creator of the popular white clam pie. Founded in 1925, and came to fame for the “Original Tomato Pie” as the neon sign hanging in front of the coal-fired kitchen indicates. Pepe’s story and history drew me in the most, and if you’re going to try apizza, might as well start with the original.

Which leads me to the white clam pie! This made for the perfect introduction to our seafood-fueled New England road trip. It was crispy, garlicky, cheesy and the touch of charring really balanced out the briny yet sweet clams. 10/10 for me.

Take a walk to burn off some calories and explore the rest of the shops of Little Italy within Wooster Square.

Option to stop in the popular seaport village of Mystic, CT to further explore Connecticut, if you have time!

Second Stop: Rhode Island

Driving Time: 1.5-2 hours

This will be the first time I am visiting Rhode Island. It’s the smallest state in U. S. and normally, we’d drive through it on our way to and from Boston. I’m so very excited to finally check this off my list. On this trip, we will visit Narragansett and then later Newport, RI on our winter road trip (blog post coming soon!).

Rocky shores of Narragansett, RI with Point Judith Lighthouse in the far distance.

Narragansett, RI

We are getting our first taste of the ocean air and New England seafood here! Narragansett is a popular city in Rhode Island during the summertime. It’s known for clam shacks serving up fried clam strips and clam cakes, rocky shores, and point of interest: Point Judith Lighthouse.

In the name of efficiency, I found Aunt Carrie’s, an awarding-winning seafood establishment located in the Point Judith neighborhood of Narragansett. The 100-year old restaurant is located right on the coast, historically known for their clam cakes (legend says Aunt Carrie’s invented it), and it’s within walking distance to the Point Judith Lighthouse. You can kind of see the lighthouse in the top photo, far in the background.

Any other Food Network lovers out there?! Did you know Aunt Carrie’s was featured on Guy Fieri’s show, Diners, Drive-ins, and Dives?

Aunt Carrie’s

1240 Ocean Road, Narragansett, RI

We had to try this place for ourselves and ended up ordering their chowder and clam bake combo with stuffies (stuffed quahogs clams) on the side. We took our order to-go and walked down to the rocky shores of Rhode Island to enjoy our second meal of the New England road trip.

There’s nothing quite like enjoying some seafood with a view of the Atlantic Ocean. If this doesn’t scream New England summer, maybe our next few stops will.

Option to stop in the super popular city of Newport, RI if you have more time!

Third Stop: Massachusetts

Driving time: 1.75-2 hours

This is the state I am most familiar with! Having lived in Boston and visited Martha’s Vineyard already, I wanted to stop somewhere I haven’t been yet. Massachusetts has so much history, legends, scenery and great seafood options. It’s hard to go wrong in this state.

Coastal towns of Nantucket, Cape Cod, and Martha’s Vineyard are favorites for summer getaways for us Northeasters. If you decide to fly in, Boston makes are great starting point for the road trip, and it’s quite a popular option, too.

Sails in the bay of the seaside town of Duxbury, MA

So, why Duxbury?

Duxbury, MA

I have two reasons why I choose Duxbury as our Massachusetts stop. The first reason is Island Creek Oysters and secondly, Vogue named it “New England’s Best Kept Secret.” Duxbury Beach is one of the best beaches to visit, south of Boston. The historic town is quite underrated and perfect for those looking for a more low-key seaside escape.

Raw Bar at Island Creek Oyster Farm

401 Washington Street, Duxbury, MA

Island Creek Oyster Farm's Raw Bar
Island Creek Oyster Farm’s Raw Bar Offerings

Now to the good part: oysters, rosé and tinned fish. We made a stop for the Raw Bar at Island Creek Oyster Farm, just in time for sunset.

A little backstory about this… My friends and I love to go to oyster Happy Hour in NYC and found our one favorite kind of East Coast oysters at Crave Fishbar (only at the UWS location at the time). This oyster is the Island Creek Oyster. We used to order it every time it was available in market. When I found out they had a raw bar that’s opened to the public at their farm in Duxbury, it was an immediate ‘yes’!

Island Creek Oysters Raw Bar
Seafood at the Raw Bar at Island Creek Oyster Farm

This is not my first visiting an oyster farm. I’ve previously did a day trip to Blue Island Oyster farm on Long Island, NY, where I did a kayak tour of the hatchery. But, this is definitely the dreamiest oyster farm and raw bar visit.

I had a such a blissful moment watching the sunset surrounded by fresh shellfish and seafood, good vibes and a cold glass of crisp rosé wine. We happily ate away into nightfall, when the fire pit got going and the string lights came alive.

Option to stop in by Boston, Martha’s Vineyard, Nantucket or Cape Cod if you have more time!

Fourth Stop: Maine (Portland)

Driving time: 2-2.5 hours

Lighthouses and Lobsters! After the oyster farm, we decided to pushed through the night and drive into Maine, our final state. I love visiting this state for the freshest lobster, beautiful hikes and nautical atmosphere. If I could, I would make annual trips up here. It’s one of those places that you could never get tired of.

We spent most of the trip eating our way around Maine. Keep reading to see where we went!

Harbor views of Casco Bay in Portland, Maine

Portland, ME

Upon arriving into Portland, the first thing we did was check into our home base for the remainder of the trip, Portland Harbor Hotel, located in Downtown Portland.

Lounge area in the Portland Harbor Hotel, Maine

It felt so good to unload and decompress a bit. I love how centrally located the Portland Harbor Hotel was to all the restaurants and sights we wanted to try and visit. Valet parking is available, and most points of interest was within walking distance from this hotel (Old Port, included). I love the plush and historical maritime vibes of this place. It’s a good balance of modern and old-timey for those into aesthetics.

We visited so many eateries in Portland. Here’s a breakdown of every place we went to and dined at. I

Porthole Restaurant & Pub

20 Custom House Wharf, Portland, ME

After a day of walking around Old Port and along the harbor, we stopped by Porthole Restaurant & Pub. It has Portland’s largest waterfront deck with plenty of outdoor and indoor seating. The lobsters here are straight from Casco Bay to our dinner table.

We ordered the twin lobster dinner, steamers, and lobster roll to share. This will be the first of many steamed lobsters and lobster rolls we will be having on the rest of this trip. We loved the steamers so much that we ordered another round. Needless to say, we were stuffed by the end of the night. Not only was the food satisfying, but we had a great view of the waterfront. We caught the dreamy sunset while waiting in line to get seated here. Perfection.

Fun fact: Porthole Restaurant & Pub was also featured on Guy Fieri’s Diners, Drive-Ins, and Dives.

Sunset on the Harbor while waiting to get seated for Porthole Restaurant & Pub.


43 Middle Street, Portland, ME

As if we weren’t full enough, we tried to make some room in our tummies for the the famous Duckfat Poutine. Because we’re extra, we ordered a fried duck egg on top of the poutine. Duckfat is know for their Belgian style frites, which are double-fried in, you guess it, duck fat. Poutine, is a fries dish from Canada that consists of fries, topped with cheese curds and gravy. Here, they use duck gravy and it’s topped with chives.

This was the best late night snack. Indulgent!!

The Holy Donut

194 Park Ave, Portland, ME

For breakfast the next day, we went to The Holy Donut for the famous Maine potato doughnuts. Ordered some doughnut selects and most importantly, iced coffee. Not to be missed is their Maine Blueberry doughnut!

Iced Coffee and Doughnuts from The Holy Donuts in Portland, Maine

Eventide Oyster Co.

86 Middle Street, Portland, ME

I had to make reservations for Eventide Oyster Company and have their Brown Butter Lobster roll once again. I had this phenomenal lobster roll the last time I was in Maine, and its by far on my Top 3 lobster rolls in all of New England and New York. They have a new location Boston now, too! (Of course, I went again on my Fall Boston trip). Eventide has a modern take on traditional and classic New England seafood fare. This is why I love this place so much. The innovative flavors on familiar dishes is done so well here.

For our big lunch, we ordered so many dishes between the two of us.

We started with a spread of raw oysters and little neck clams. I really loved the pickled red onion ice as the accoutrement for the raw shellfish. This Bluefin Tuna crudo with ginger-scallion oil was a banger. My mouth was so happy and dancing. Next, we got the Maine Lobster Stew with green coconut curry and the brown butter lobster roll.

Eventide Brown Butter Lobster Roll, Portland, Maine

We really wanted to order the New England Clam Bake, but it was all sold out for the day! There is always next time, since I definitely keep coming back, given the chance. To end the wonderful meal, we got an Ice Cream Sandwich with chocolate chip cookies and vanilla ice cream. Chef’s kiss. 10/10 meal.

Fifth Stop: Maine (Cape Elizabeth)

Driving time: 18 minutes

We are back on the road, headed south towards New York, and will be stopping for more seafood shacks within Maine, before we drive all the way back home.

Classic Summer New England Road Trip
Leafy and scenic in Cape Elizabeth, Maine with the Cape Elizabeth Light Tower in the back

Cape Elizabeth, ME

Lush greenery, colorful blooms and rocky shoreline greet us upon arrival to the coastal area near Two Lights State Park. It was golden hour and everything looked extremely dreamy. Two Lights refers to the twin Light Towers in Cape Elizabeth. One twin light is closed and is private property while the other is still open and active.

On the rocky coastline of Cape Elizabeth near Two Lights State Park
Classic Summer New England Road Trip

Lobster Shack at Two Lights

225 Two Lights Road, Cape Elizabeth, ME

It wouldn’t be a stop on the New England road trip, if we didn’t have a seafood break. We ordered the lobster dinner with fries and biscuits. It tasted sweet and as fresh as it could be. Like many of our coastal meals, this was also very scenic and relaxing. If you haven’t learned to properly crack open a lobster before a trip to Maine, I’m sure you’d be a pro by the end of it.

Classic Summer New England Road Trip

Final (Sixth) Stop: Maine (Kennebunk & Kennebunkport)

Driving time: 40 mins-1 hour

Kennebunk and Kennebunkport are really popular towns in Maine during the summer for the beaches, shopping and dining. If you love a historic town with some great local fare, these are great ones. The two are quite close to each other and separated by a river. The Matthew J. Lanigan bridge connects the two towns over the Kennebunk River.

Kennebunk, ME

To round out the seafood feasting we’ve been doing, we stopped by award-winning, The Clam Shack. This place has been on my radar for years. Their lobster roll has won multiple competitions! Unlike your usual lobster roll, they sandwich all the sweet meaty goodness between a round white roll (burger bun), instead of your typical hot dog bun.

The Clam Shack

2 Western Ave, Kennebunk, ME

We decided to order the clam strips and it was so crispy delicious! It was truly such a nice way to close out the New England road trip. We finished our meal with a sunset view of the docks along Kennebunk River.

Kennebunkport, ME

After getting our fill, we walked over the Kennebunkport Bridge to the town next door to stroll the historical streets and check out the shops until nightfall.

Bridge connecting the towns of Kennebunk and Kennebunkport, Maine
The Boathouse Waterfront Hotel & Restaurant, Kennebunkport, Maine

Our New England roadtrip was filled with plenty of sweet lobster, a plethora of shellfish, rocky shorelines, fresh salty ocean air, and historic ambiance. After this last stop, we powered our way down the highway back home to New York City.

For more New England posts, click HERE.

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