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NYC city break ideas, new york city

Boston to New York Road Trip Itinerary Goals

The road from Boston to New York City is a cool 215 miles through Connecticut via the I-90. With your foot on the gas and a good following wind, you could comfortably make the journey in around four hours. But where would be the fun in that?


A Boston to New York road trip is a great experience, and one of the best ways to get to grips with the glorious landscapes of New England. So why not take your time and enjoy it.


You can turn that four hours into four days, meander your way down through Massachusetts, Rhode Island, and Connecticut, then cruise from the New York port to wherever you want to go next!


This Boston to New York road trip itinerary showcases the best that New England and New York City have to offer.

Boston to new york road trip, lighthouse, cape cod, massachusettsBoston to New York Road Trip Goals

Day One – Boston to Providence

Head southeast from Boston, the vibrant capital of Massachusetts, towards Plymouth, hugging the coast till you reach Providence. Here you can admire the colorful murals downtown and take a walk along the river for a delicious plant-based lunch at Plant City.


With plenty of time to spare, it is well worth exploring the beautiful beaches of Cape Cod, which are another hour or two away. Make sure to stop at the many quaint seaside towns along the way, like Plymouth, Barnstable, Wareham, or New Bedford.


Finish the day’s drive in Providence, the charming capital of Rhode Island, full of delightful 18th- and 19th-century architecture, some excellent museums, and Brown University. Don’t miss the eye-catching WaterFire installation which lights up the center of town on summer nights.

Boston to new york road trip, newport

Day Two – Providence to New Haven

Jump back in the car and hit the road south towards Cranston, Kingston, and North Warwick. Hang a left after North Warwick, across to Aquidneck Island, and spend the morning exploring beautiful Newport.


There’s some fantastic colonial architecture, historic Fort Adams, and the Brenton Point State Park to explore, as well as a bunch of gorgeous and decadent 19th-century mansions (Jay Leno owns one!).


Later on, stroll down Bowens Wharf and onwards to Thames Street to explore the quaint stores and cafes lining the road.


Providence is the hometown of some of the country’s most famous and most successful theater and music companies, including the Trinity Repertory Company and the Rhode Island Philharmonic Orchestra. If you have time, try to catch a show or a concert at the Providence Performing Arts Center, a real cultural treat. 


Once you’ve finished in Newport, head west into Connecticut, and enjoy the views of Long Island Sound, and Long Island itself, out of the left-hand window. Drive through New London and Old Saybrook until you reach New Haven, your destination for the night.

Boston to new york road trip, new haven, yale

Day Three – New Haven to New York

New Haven rarely gets a huge write-up anywhere, but it is one of the most underrated cities in New England and well worth exploring. There’s a fantastic dining scene here, as well as numerous historical and cultural touchpoints, not least of which is Yale University.


The free campus tours at Yale are a surprisingly fascinating way to spend a couple of hours, and you’ll learn about everything from the rarest books in the library to the secretive Skull and Bones fraternity! There are also various excellent museums scattered about town to scratch your cultural itch.


As we mentioned above, New Haven has a surprisingly brilliant dining scene and was named Best Foodie City in the US by in 2014. There’s a wonderful variety of cuisines and restaurants like McDonald’s and Subway or Wendy’s on show in the city center (over 120 eateries within two blocks of New Haven Green).


New Haven even boasts the most Zagat-rated restaurants in the state. Don’t miss the opportunity to try a pizza, the local version of pizza, widely considered to be the best in the US and capable of giving genuine Neapolitan cooking a run for its money!

NYC city break ideas, new york city
Photo by Emiliano Bar on Unsplash

Day Four – New York City

Exploring and eating done, the last drive is an easy one, southeast along the I-95 for a couple of hours until you find yourself surrounded by the bright lights of New York, New York!


If you have never been to New York City, it is best to spend a day here at the end of your road trip. Since you can’t expect to cover everything in one day, just choose either one of the neighborhoods of Soho, Theatre District, Midtown East or Lower Manhattan. 


In New York City you are bound to find something interesting, whether it is a dining experience, a stroll in Central Park, Broadway shows, or museums. End with a walk over the Brooklyn Bridge. Remember to get your New York City card in advance to save time at different tourist attractions.


Insider tip: The best time to do the Boston to New York road trip is early October. Not only is it a tourist-free time, but the weather is amiable as well. Also, if you’re looking for affordable rates on places to stay you should check out MotelMatcher.


In Closing

There are many adventures to be had on a Boston to New York road trip. Be sure to travel safe, take loads of pics, and make lots of memories along the way!

Carissa Shuman

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