New England Summer Road Trip (One Week Itinerary)

Holding plate of raw oysters in New England

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My mother grew up in a small lake town in Western Connecticut. I suppose that’s how it all started, the annual family New England road trip. 

I was born and raised in NJ, but really, my brothers and I grew up New England. Our summer and holiday weekends were often spent on that grueling strip of I-95 that stretches between New Jersey and the northern part of the country.

Between my grandparent’s house in Connecticut, a beach house in a small fishing village on the coast of Rhode Island, and my father’s annual meeting in Bar Harbor, Maine, I got to know New England intimately. It has some of my happiest childhood (and later, adulthood) memories.

Long after my family had drifted apart and those road trips stopped I continued to explore, taking my own family (AKA Joe and Della pup) along this very route.

New England is downright gorgeous.

It’s allll the cliches. Small cities filled with charming cobblestone streets, tiny, snow covered homes, and old-school Main Streets. 

It’s also small geographically. Like, you can drive from the tip of Connecticut to the tip of Maine in half a day, small. 

Though we won’t be doing that here. Here, we’re showing you how to take your time and absorb some of the most scenic spots — filled with the best food, obviously — in a week’s time.

In this one week New England road trip itinerary we’re sticking to the New England coast, perfect for cruising in the Summer or Fall months.

P.S. Going for longer than a week? Check the end of the post for suggestions on how to extend your road trip through other New England hot spots.

Steps to Plan the Best Road Trip in New England

1. Plot your route

Where are you leaving from? What are your “can’t misses?” Where do you want to stay? Our itinerary below is a guide…you can follow it exactly (because it’s freaking awesome) or you can pick and choose which works best for you to form your own path.

2. Check your route against the weather. 

This is so often overlooked! Plan your route as loosely as possible. This way, you can quickly pivot if the weather is threatening to ruin your plans. It allows you more flexibility, so when there is rain forecast on the day you want to go to Acadia National Park, you can easily switch it to another.

Obviously take this with a grain of salt…weather is weather, and in New England, weather is usually unpredictable, so bring a sense of humor. As they say up around here:

“There’s no such thing as bad weather, just bad clothing” or, my personal favorite, “If you don’t like the weather, wait 15 minutes” 

3. Follow your heart

This applies to every travel experience. If you plan an activity and it sucks, BAIL. If you find a local seafood restaurant on the side of the road where a grandma-looking lady is frying fish…slam on those breaks immediately. 

When should you go on a new england road trip?

I’m going to say that SUPER annoying thing we all hate and say…it depends! Road trips in New England can vary depending on the weather. Let’s break it down by season:

Winter-Less crowded
-Winter sports! (skiing, snowshoeing, etc.)
– Unpredictable weather and blizzards
-Potentially bad driving conditions
-Seasonal restaurants closed
Spring-Scattered REALLY nice days
-Cheaper, quieter
-Catch seasonal food spots before they get too busy for the season
-Crappy weather (rainy, cold) early in season
-Too cold for beaches
Summer-Best weather for beaches, hiking, camping
-Seasonal seafood restaurants open
-Insects! Not harmless spiders, but biting mean little things
Fall-Gorgeous scenery (helllooooo leaf peepers)-Crowded
-Expensive on weekends and when leaves are at peak

How does this itinerary work?

This itinerary leaves from the New York City metro area, but you can hop on or off at any point along the way. 

If you’re in upstate New York simply head west until you reach I-95 (or check out these New York day trips instead.

Leaving from further South? Trying extending the road trip through Philadelphia–stopping for a pizza break–or go for a scenic run on the New Jersey shore.

One Week New England Road Trip Itinerary

Napoli style pizza in new haven connecticut

Day 1 Connecticut

Start your New England road trip off by cruising north from New York City and into Connecticut, possibly the most underrated of the New England states. The southern part of the state is mostly made up of wealthy New York City suburbs, so we’ll skip right over that. 

The first stop will be a welcome break from the traffic you’ll likely be sitting in on I-95. New Haven is known for two things:

1. Yale and–more importantly in our book–
2. Pizza

We’re the type of people who took a train to Naples just to eat pizza for 6 hours straight, so you know we couldn’t miss the opportunity to explore what folks claim to be the best Napoli style pizza this side of the Atlantic.

The best pizza in New Haven is debated with a ferocity that you probably don’t need to involve yourself in as a brief visitor.

Instead, just trust us and head to Modern Apizza for the best pie in the city. 

Or, if you want to do the tourist thing, check out the clam pies at Frank Pepe Pizzeria Napoletana. It wasn’t our favorite, but its been around for almost 100 years (which earns lots of respect in its own right).

Expect to wait in line for hours if you choose this spot.

If you’re one of THOSE people who don’t like pizza, there’s a great selection of taco trucks in a parking lot next to I-95. This is the spot to sample actual Mexican food, like beef tongue and tripe. 

And if you don’t like pizza or tacos…you’re honestly on the wrong blog.

Once you’re done consuming your body weight in pizza and/or tacos, hop back in the car and drive an hour north to Mystic, Connecticut. 

This little seaside town is a straight charmer. Fun fact: it’s also where the ultra-80’s classic Mystic Pizza was filmed, much to my mother’s delight. It’s worth spending a night here to tuck into one of the many B & B’s and snuggle up next to your boo.

Mystic Aquarium is great for all you fellow marine nerds (good for the kiddos and rainy days, too). When you wake up in the morning, head to Kitchen Little at Mystic River Marina, order the Lobster Benedict, and then call me immediately to thank me for starting your day off with such a marvelous treat on your tongue.

Where to Eat in New England

  • New Haven
    • Pizza at Modern Apizza, 874 State St, (203) 776-5306
    • Tacos at Taco trucks, 351 Long Wharf Dr in Long Wharf Park, varied
  • Mystic

Where to Stay in Mystic, Connecticut

We’ve actually never stayed in Mystic ourselves so can’t personally recommend anything, but taking a dip in the gorgeous looking pool at House of 1833 Bed and Breakfast feels like something we’d be very into.

Fried fish sandwich being held up at Rhode Island restaurant with boats and ocean behind
Fried fish sandwiches along the sea in Rhode Island

Days 2-3 Narragansett, Rhode Island

The smallest state in the union is also one of our favorites. Rhode Island is not, in fact, an island as I’m sure you’re all aware. However, thanks to its 400 miles of coastline, it still lives up to its “Ocean State” nickname. 

Rhode Island beaches are the main thing that draws us here every summer, though you could easily spend time praising the marshy and wooded trail walks as well.

Up north near Newport, beaches are steep rocky cliffs lined with old mansions. Down in the southern edge of the state–our fave–beaches are soft, sandy strips backed by grassy dunes.

Specifically, it’s the beaches in Rhode Island’s South County that have captured our hearts. They’re the reason we go back year after year, aside from the fact that we have family there.

Plus, this area is filled with some of our favorite seafood restaurants of all time.

These are some of our favorite South County beaches:

  1. Galilee Beach – little bit more of a local scene on a GORGEOUS beach
  2. Narragansett town beach – go surfing (or hang and watch!)
  3. Point Judith Lighthouse – rocky cliff facing out to the sea, can catch sunset views here depending on the time of year

Narragansett is a great little town to use as your home base here. It’s the home of URI and has a smattering of chill beach bars and delicious food.

Between beach trips, head into town for a fresh juice or smoothie at the hole-in-the-wall Crazy Burger, or do a fancy pants date night over at Coast Guard House, where you can sip on chowder while watching the Atlantic Ocean crash into the rocks outside the oversized glass windows.

If you really want to enjoy the scenery and the locavore seafood here, though, hop in the car and ride over to Matunuck Oyster Bar

Perched on the marsh where the oysters are grown, owner and aquaculturist Perry Rasso has grown this restaurant into a gorgeous indoor-outdoor space, serving up oysters as soon as they’re pulled from the water.

Our trips to Matunuck Oyster Bar usually consist of us waiting two hours for a table outside, cracking open a bottle of champagne, and watching the tide roll in and out while we slurp down dozens of our favorite salty little bivalves.

Honestly, I could (and usually do) spend a week here in Rhode Island and go nowhere else. It is the ultimate combination of rest, sweet salt air, and ultra-fresh seafood that my body craves after a long winter.

But you’re on a mission to explore New England on this road trip, so stop off for a night or two and then head North.

Where to Eat in Narragansett, Rhode Island

Where to Stay in Narragansett, Rhode Island

We’ve stayed at the Aqua Blue Hotel before which was ok (the location is AMAZING literally steps from the beach and Coast Guard House for dinner, although you pay for that) but we’ve heard GREAT things about The Break Hotel.

Rhode Island beach at sunset
These Rhode Island beach sunsets though…

Days 3-4 Massachusetts

Hop back on I-95 and head north until you hit Boston, your next stop on this New England road trip.

Boston is a little city that feels like a little city, but with a bunch of strangely aggressive folks who drink a lot. I don’t mean that as an insult…Boston is a lot of fun. And being from New Jersey where people also tend to be angry at random times, these are my kind of people.

In all seriousness, Boston epitomizes so much of what is great about New England in an urban setting. The cobblestone streets are crammed with history and lined with tiny row houses that look straight out of a Charles Dickens novel. 

Fenway Park, the oldest operating baseball stadium in the country, sits in a charming downtown neighborhood with great food.

Boston’s Little Italy in the North End still has pasta cooking grannies rolling out dough by hand, and there are a delightful craft beer and food options everywhere you look.

The harbor is kept shockingly clean (coming from New York) and love it or hate it, Cambridge and Harvard are downright stunning.

Spend a full day exploring the historical sites, catching a Red Sox game, or touring the eclectic Harpoon brewery on the harbor. 

I’m also a sucker for the original Legal Sea Foods, though it’s recently moved and I’m not sure it’s worth it without the nostalgia factor.

Before you continue on your New England road trip, make time for a quick pit stop in Ipswich, MA.

It’s an adorable little town jutting out into the Atlantic Ocean that also happens to have some of the best fried clams EVER! Argue it…I dare you.

Then, continue North… 

Where to Eat in Massachusetts:

Where to Stay in Boston, Massachusetts:

There’s literally an option for anyone when it comes to hotels in Boston. Click here to see a full hotel list with 100’s of options in every budget and style.

Pine trees along a cliff trail in Acadia National Park
Hiking trails along the cliffs in Acadia National Park

Day 4-6 Maine

Maine, you crafty, beautiful genius! How did you get to be so wild and stunning?

The lobsters…the pine trees…the rocky majestic coast…Maine is the epitome of when you just can’t even.

Here’s how you spend 2 days in Maine.

First off, go to Acadia National Park. Just go right there. Because as beautiful and amazing as much of the rest of the state is…Acadia is the masterpiece of it all.

Plus, with only a couple of days to explore, it’s the easiest way to see the best of what Maine has to offer.

Camp inside the park (Blackwoods Campground is the best if you can get in) or head downtown to Bar Harbor for a home base. Hotels here aren’t cheap, though, so plan ahead for this.

Take whale watching trips off the coast, hike the winding ocean-view hugging trials, scramble up rock faces, or just eat lobster rolls every hour on the hour.

One time, Joe ate lobster for every single meal for a week straight in Bar Harbor…it wasn’t cheap or particularly healthy, but it was impressive. And, he was happy. 

You can see the first sunrise hitting the continental US from Cadillac mountain (note: this gets really crowded) and head down for early morning blueberry pancakes at Jordan’s Restaurant.

Or, head out to pick wild blueberries yourself. They’re much smaller than the traditional grocery store ones, all the easier to pop them in your mouth like candy. In season, you can find them hugging the trails, or you can stop by a local farm.

Where to Eat in Maine:

Where to Stay in Bar Harbor, Maine:

Bar Harbor Inn is where I stayed every time growing up. Even after decades in use, it’s managed to stay modern and refined. I love the charming rooms, elegant feel, and actually good breakfasts here. Oh, and it just so happens to be on the ocean (think listening to the waves crashing on the rocks beneath you…DREAMY). Granted…my parents were floating the bill then, it’s not cheap, but SO worth it if you can swing it.

Click here to book The Bar Harbor Inn if you want to ball out on some luxury.

Or try Camping at Acadia National Park.

Day 7 On the road back home...

Head home, OR just never leave, We won’t judge.

Not sure where to stay? Use the search box below to find the best hotels in Connecticut, Rhode Island, and everywhere else in gorgeous New England.

Options to extend your New England road trip:

Add a night, day, or as long as you’d like on through some of these great additions:

  • Portsmouth, NH – this trendy little harbor town gets its fair share of local tourists but isn’t often on the radar for outsiders. Be in the know and visit.
  • Portland, Maine – one of our all-time favorite cities, Portland feels more like a small town, albeit one on the rugged Maine coast that happens to have exceptional dining.
  • Burlington, Vermont – a hippy college town at it’s finest, lake-front Burlington is a bit out there but well worth the segway.
  • Cape Cod, MA – come for pictures of the wood-shingled beachfront mansions, stay for the local pubs serving up piping hot seafood chowder and freshly fried, fish.
  • Block Island, RI – this reminds us a lot of Ireland, it shares the romantic feelings and rolling, green hills. We like to take the ferry over and rent a bike, which will easily take you around the entire island.
  • Kennebunk, Maine – Which we hit up on a different new England road trip (also where that lobster roll pic was born!!)

Road Trip Destinations in New England

It’s worth time to come up to New England just to stop at any one of these spots.

  • Acadia National Park – For the unreal, oceanfront hiking.
  • South County Beaches – For pristine, sandy beaches.
  • New Haven – For the pizza and tacos.
  • Boston seaport – For the charming, small city feel.

What is there to do in New England in Summer?

Soooo many things! 

  • Bake your skin on the sandy beaches
  • Hiking! Best in the Northern parts in my opinion (Vermont, New Hampshire, and Maine) but there are still great forested trails in Connecticut and marshland walks in Rhode Island
  • Kayaking, canoeing, and stand up paddleboarding on lakes, rivers, marshes, and the Atlantic Ocean…oh my!
  • Eating all of the fresh, local seafood like a maniac

New England Road Trip Map

New England Road Trip Map

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Miles Less Traveled

We are the dynamic running duo that run this site. Lovers of new places, bridges, and all the food.


  1. Frank
    October 3, 2021 / 8:13 AM

    Returning to NYC / New England for first time in 20 years for family road trip. . Grew up on Pepe’s and Modern Pizza, and many other things you mentioned about Connecticut were spot on, love the recommendations throughout your articles. Will be using a lot of this information to help plan out our New England Summer vacation. Thank you for taking the time to share.

    • Miles Less Traveled
      October 3, 2021 / 3:43 PM

      Thanks Frank! So glad you found it helpful

  2. Charlene
    February 19, 2021 / 10:54 AM

    Should we travel on over to Plymouth since we’d be so close?

    • Miles Less Traveled
      February 19, 2021 / 11:04 AM

      Hey Charlene, that’s a great idea! We’ve actually never visited Plymouth but from what I’ve heard about it I’m sure it would make a great addition

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