What to See on a New York to Boston Road Trip Filled With History

by Holly Riddle
Updated January 12, 2023

new york city to boston road trip
Photo: Sean Pavone

When traveling between New York City and Boston, you can get between the two East Coast hubs in a matter of a few hours.

It really only takes about four hours to traverse the just-over-200 miles, so you could essentially get there in a single morning or afternoon. But rather than simply spending all of your time in Boston, why not stretch the trip out a bit and enjoy all the historic sights and sounds located between the two cities? 

Below, you’ll find a brief breakdown of how you can turn your quick jaunt from NYC to Boston into a weekend road trip worth talking about. While the route follows I-95N and I-90E, you’ll find that there are some awesome side trip opportunities along the way, that could extend your trip even further — You could even turn this four-hour trip into a whole week-long experience if you truly tried! There’s certainly enough to see and do. 

Related Read: Top 10 East Coast Vacation Spots You Never Considered (But Should!)

NYC to Boston Road Trip by Segment

As mentioned, the quickest (and most popular) route from New York City to Boston is via the series of interstates that easily connect the two — I-95N, I-91N, I-84E and I-90E. Honestly, the whole trip is so simple that you barely need a map. If you can remember a few turns and merges, you’re there. 

Luckily, these interstates offer plenty of spots to get off and see the sights, quickly and conveniently, so it’s not like you’re just staring at bland, boring highway the entire trip. For our road trip, we’re splitting this route into two sections: NYC to Hartford, Connecticut, and Hartford, Connecticut, to Boston, with potential side trip opportunities in Tarrytown, New York, and Newport, Rhode Island. 

Keep in mind, if you’re planning an East Coast road trip like this for the winter, you’ll want to plan accordingly. Harsh temperatures and unpredictable snow can make travel times much longer.

Related Read: 7 Weekend Trips From NYC With or Without a Car

Segment 1: NYC to Hartford 

If you’re staying in Manhattan, your drive to Boston is going to take you up through the Bronx and into Connecticut, where you’ll follow the coast up I-95, until you reach I-91. 

  • Distance: 118 miles
  • Drive time without stops: 2 hours

Segment 1 Highlight: New Haven, Connecticut 

nyc to boston road trip new haven
Lighthouse Point on the Long Island Sound in New Haven. Photo: Shutterstock

Unless you take the Tarrytown side trip (more on that in a minute), your first highlight stop on our itinerary will be at very nearly the halfway point overall — because, really, things don’t get very interesting until you’re well away from Manhattan. 

New Haven, Connecticut on the Long Island Sound is a lovely little coastal city that’s a hub of history, partially thanks to its status as the home of Yale University. You’ll find lots of great museums and galleries to visit here, such as the Yale Peabody Museum of Natural History, the New Haven Museum, the Yale University Art Gallery and the Yale Center for British Art.

For those who like a bit of spooky history, Grove Street Cemetery is a must. For a more whimsical museum experience, visit the PEZ Visitor Center — yes, it’s a museum space dedicated to the PEZ candy. And, for a bit of fresh air, try the beach at Lighthouse Point Park or hiking at East Rock. 

Related Read: The 11 Best Things to Do in New England This Year

Segment 1 Highlight: Meriden, Connecticut 

nyc to boston road trip meridian ct
Castle Craig at Hubbard Park in Meridian. Photo: Shutterstock

About halfway between New Haven and Hartford, you’ll find the smaller town of Meriden. It’s only about a half-hour drive from New Haven, so you won’t find yourself spending much longer in the car to get between the two.

Meriden offers plenty of spots for you to stretch your legs, in case you didn’t happen to stop over in New Haven. Castle Craig in Hubbard Park is a popular hiking destination. The 120-year-old tower offers views as far away as the Berkshires, Hartford and the Long Island Sound. 

Related Read: 8 Tranquil Cabin Rentals in Connecticut

Segment 1 Side Trip: Tarrytown, New York

nyc to boston road trip tarrytown
The Lyndhurst estate in Tarrytown. Photo: James Kirkikis

If you do want to take a little side trip before entering Connecticut, you can do so as you head out of Manhattan, by going a little west before you head northward, to Tarrytown, New York. This very small village on the Hudson River is known for its connections to Washington Irving’s Sleepy Hollow, as the village by the same name is within walking distance. History and architecture buffs will love the wealth of interesting sites, such as Lyndhurst, a Gothic Revival mansion, and Sunnyside, Washington Irving’s historic home.

If you’re looking for a spot to stay the night as you explore the area before traveling on to Connecticut the next day, consider Castle Hotel and Spa, which is just as elegant and, yes, castle-esque as you expect.  

Related Read: 12 Best Spots to See New York’s Fall Foliage

Segment 2: Hartford to Boston

Once you’re in Hartford, you really should consider sticking around for a while. The city may not get as much hype as Boston, but it’s jam-packed with interesting things to do and see, no matter what kind of traveler you are or who you’re traveling with.

Literature lover? You’ve got The Mark Twain House & Museum and the Harriet Beecher Stowe Center. Art fiends? There’s the Wadsworth Atheneum Museum, with all its 1800s and 1900s artwork. Kids in tow? Try the Connecticut Science Center. And when you’re done with all the museum hopping, you’ve got endless options for shopping and dining, as well as hotels. 

But, once you’re ready to move on with the second leg of your journey, you’ll find that you’ll want to take I-84E and I-90E all the way to Boston. However, there are a few stops that you’ll want to make (and maybe a fun side trip), even though the trip between Hartford and Boston is only  a mere 100 miles and less than two hours. 

  • Distance: 101 miles
  • Drive time without stops: 1 hour, 35 minutes

Related Read: 10 Chill Romantic Getaways in Massachusetts

Segment 2 Highlight: Sturbridge, Massachusetts 

A rural scene reminiscent of the early 1800s in Old Sturbridge Village. Photo: Ritu Manoj Jethani

Right after you cross the Connecticut-Massachusetts border, you’ll find Sturbridge, Massachusetts, a small town that dates back nearly 300 years and is most well known for Old Sturbridge Village, a living history museum that depicts 18th-century New England life. It’s a nice way to get to know the area’s history, without being cooped up in a museum.

And for more outdoor adventure, visit Wells State Park, which offers a wealth of outdoor recreation regardless of the time of year you visit. Hiking, biking, skiing, swimming — there’s a little bit of it all. 

Related Read: 10 Best Airbnb Rentals in Massachusetts

Segment 2 Highlight: Worcester, Massachusetts

nyc to boston road trip worcester
Fall colors at the historic Elm Park in Worcester. Photo: Jay Yuan

If you’re willing to get off the interstate for a bit, you’ll find Worcester, Massachusetts (pronounced “wuh-stir”), and, yeah, even more amazing museums, art galleries and ways to learn about this culturally-rich slice of New England.

There’s the Worcester Art Museum and American Antiquarian Society for the art and history-lovers. For traveling families, the EcoTarium is an awesome educational spot that blends indoors and outdoors for a kid-friendly experience. More outdoor fun can be had at the nearby Tower Hill Botanic Garden or Elm Park. If you visit during the winter months, you can find conveniently-close skiing at Ski Ward Ski Area. 

Related Read: 10 Terrific Tiny House Rentals in Massachusetts

Segment 2 Highlight: Arriving in Boston

nyc to boston road trip back bay
Boston’s lovely Back Bay neighborhood. Photo: Jorge Salcedo

Of course, once you arrive in Boston, you have a wealth of interesting things to add to your itinerary, no matter what it is you want to do, whether you’re staying for a weekend or a week.

Whatever you do, though, make sure that you take your time to walk Boston’s Freedom Trail, a 2.5-mile route that takes you to more than a dozen historically-significant spots around the city. Likewise, don’t miss exploring the Back Bay neighborhood, with its world-class shopping, galleries and quaint local dining spots.

If you’re lucky enough to visit during the baseball season, a stop by Fenway Park is also requisite, even if you don’t care at all for the sport; after all, even if you aren’t quite sure on the rules, who can pass up the opportunity to kick back in the sunshine, hot dog and beer in hand, for a few hours?

Related Read: The 15 Best Hiking Trails Near Boston, Massachusetts

Segment 2 Side Trip: Newport, Rhode Island 

nyc to boston road trip newport ri
Newport Harbor Lighthouse and Newport Bridge. Photo: Olga Enger

While the inland route between Hartford and Boston is the quickest way to get between the two cities, if you head to the coast, you’ll find gorgeous scenery awaiting in quintessential New England coastal towns — like Newport, Rhode Island.

Traveling to Newport after you leave Hartford and before you get to Boston really doesn’t add too much time to your itinerary (you can get between the two cities via Newport in just over three hours and 150 miles), but the detour is well worth it once you’re exploring the waterfront, driving along the Ocean Drive Historic District scenic route, and exploring the many historic sites, from lighthouses to opulent mansions. 

Related read: 8 Unique Places to Stay Near Boston When You Need to Get Away

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