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 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.
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.