The Perfect Itinerary for a New York City to Boston Road Trip

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From Broadway shows to the Green Monster, a road trip from New York City to Boston is one to remember.

NYC and Boston are only about 200 miles apart. And yet, despite the small distance, there are boatloads of things to see between them. Thanks to the stunning scenery and New England’s historic towns, the short journey is made incredible thanks to its enchanting surroundings.

From theme parks to towns made famous by movies, here’s the perfect itinerary for anyone making the trip between Beantown and the Big Apple. So buckle up and bring a snack, because here we go.

New York City to Boston Road Trip Section by Section

There are two basic ways to go from New York City to Boston. You can go north through New York and then head east on I-90 or immediately go east along I-95 which brings you straight into Boston.

One way traverses mountains and quaint, artsy towns while the other skirts along Long Island Sound and coastal hamlets. Instead of telling you to pick one or the other, below is an itinerary of doing a loop road trip, where you start and end in New York City.

Segment 1: New York City to Hudson

Distance: 120 miles
Drive time without stops: 1 hour and 50 minutes

Segment 1 Highlight: Take a hike

You can’t drive through the Hudson Valley without hiking to see the namesake river in all its beauty. If you’re looking for an easier jaunt to take in the vistas, consider hiking up to the summit of Storm King Mountain. The two-and-a-half-mile hike brings you up and down the mountain with sweeping views of the valley without too much effort.

For a bit of a harder hike (and a much less-populated path), head to Mount Beacon Park. To get there, just go north of Storm King Mountain and cross over the river to its eastern banks. Here you’ll take the trail up to South Beacon’s fire tower for 360-degree views.

Segment 1 Highlight: Walk around the quaint town of Hudson

Several small and historic towns dot the shoreline along the Hudson River. None compares to the downtown of Hudson though. With dozens of restaurants, shops, and places to explore, you’ll never be bored.

I suggest checking out the local flower shop called Flowerkraut where you can get both flowers and amazing sauerkraut. Or, pop into one of the many home furnishing stores like FINCH Hudson, Red Chair, and MINNA.

End your day at The Spotty Dog Books & Ale where you can get lost in the latest thriller while sipping on some beers.

Segment 1 Side Trip: Release your inner child and head to LEGOLAND

Located just north of New York City in the small town of Goshen, lies a new addition to the Northeast. LEGOLAND opened in 2021 and since its inaugural year, it just keeps getting better and better. Whether you’re a kindergartener or a retiree, LEGOLAND has something for everyone.

There are rides for little kiddos, a few rollercoasters, and a water playground. But the real gem of the park is their various LEGO-building areas where you can put your creativity to the test and construct whatever your heart desires.

Segment 2: Hudson, NY to Boston, MA

Distance: 160 miles
Drive time without stops: 2 hours and 45 minutes

Segment 2 Highlight: Head back to the 1800s in Old Sturbridge Village

Step back in time to the early 1800s when life was slower. Old Sturbridge Village covers 200 acres and houses 40 historic buildings where visitors can walk around and immerse themselves in what it was like centuries ago. Workers are in full costume and won’t understand you if you talk about Taylor Swift or TikTok.

Don’t try to trip them up because they’ll never break character no matter how hard you try. If you’re lucky enough to visit during early August, their annual “Redcoats & Rebels” re-enactment is something to behold.

Segment 2 Side Trip: Walk around Northampton

If you can swing it, the town of Northampton is well worth the side trip north of the I-90. It’s got a great main street where you can shop, dine, and people-watch for hours. It’s known as an artsy town with dozens of art galleries, quirky shops, and eccentric locals that bring a lot of character to this small town.

One place to note is Bluebonnet Diner, where patrons will feel like they’ve gone back to the 1950s in this train car-style restaurant complete with chipped coffee mugs. If you’re looking for a bit more elegance, head to Homestead where the head chef brings old-fashioned Italian cuisine to New England. Cap off your night at the Tunnel Bar where you can sip a wee dram of whisky while sitting underneath Union Station, which was used by travelers back in the late 1800s.

Segment 3: Boston, MA to Mystic, CT

Distance: 100 miles
Drive time without stops: 1 hour and 45 minutes

Segment 3 Highlight: Providence

The capital of Rhode Island might seem small compared to the cities of New York and Boston, but it’s got a lot to see within its borders. The world-renowned Rhode Island School of Design (more commonly known as “RIS-dee”) has a museum that holds incredible works of art from artists across the world.

Speaking of art, check the schedule for the lighting of WaterFire – a mesmerizing art exhibition within Waterplace Park. Other places to visit include the Providence Athenæum, a public library that looks like a museum, or the Roger Williams Zoo.

Segment 3 Side Trip: Get all witchy in Salem

No matter the time of year, Salem brings all the Halloween vibes. Whether you are a history buff, one who believes in ghosts, or just a huge fan of Bewitched, Salem will not disappoint. For those wanting to know about the history of the town, consider stopping in at The House of Seven Gables, the Salem Pioneer Village, or the Salem Maritime National Historic Site. If witches are what you’re after, make sure to pop by the Salem Witch Museum, The Burying Point, and The Witch House of Salem.

If you’re just there to have a good time and see the sights, start at the Peabody Essex Museum. Then walk along the main drag to hit up some of the quirkiest shops. For those wanting wands, head to Wynott Wands; for books, Wicked Good Books; and for general witchiness, Crow Haven Corner or the Coven’s Cottage are your best bet. 

Segment 4: Mystic, CT to New York City

Distance: 130 miles
Drive time without stops: 2 hours and 45 minutes

Segment 4 Highlight: Head to a beachside carousel

Before you leave Mystic, head to Watch Hill to catch some sun rays and get a little taste of the Atlantic Ocean. You might get a glimpse of Taylor Swift since she bought a seaside mega mansion here. But the town is known more for its beach than the celebrity residents.

Watch Hill Beach (also known as “the one with the merry-go-round”) can get very crowded but rightly so. The surf is calm, the sand is soft, and the views go on for days. If you ride the carousel, make sure to pay for an outside horse ticket so you can play the Brass Ring game and have a chance at snagging a free ride. There’s also a Nature Conservancy protected area called Napatree Point Conservation Area (my suggestion is to visit this place at sunrise when visitors are few).

Segment 4 Side Trip: Block Island

Hop on the Block Island Ferry and sail to the small island within Long Island Sound. Make sure to book out a whole day to experience the entirety of Block Island.

It’s well known for its beaches but there’s a lot more to do than just sunbathe. There are more than 50 stores on the island, each with its own unique spin on island life. Block Island Trading Company is the perfect place to grab a souvenir while the Island Bound Bookstore will keep your reading needs up to speed as you lay in the sun.

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