Boston to New York: Roadside Road Trip Attractions That You Don’t Want to Miss

Driving From Beantown to the Big Apple? These Are Some of Our Favorite Places to Stop on the Way!

 The City That Never Sleeps, Empire City, the City of Dreams, the Big Apple—whatever you call it, when it comes to timeless travel destinations, New York City is pretty hard to beat. If you’re coming from Boston, the drive to NYC is only about 4-and-a-half hours. And while you definitely won’t be short on things to see once you get there, why miss out on all of the gems that you’ll pass on your way down the East Coast? 

With so much history and such a variety of points of interest, New England has something for everyone—which is why it’s full of road trip potential! These are just a few of the destinations that you’ll have to choose from when driving from Boston to New York. 

Plimoth Plantation 

📍 Plymouth (MA)

See What Life Was Like For the Pilgrims at This Living History Museum 

137 Warren Avenue | Historic District |

The city of Plymouth lies about an hour south of Boston, and as the site where the pilgrims first came over from Europe on the Mayflower, it’s one of the historic areas of the country that every American should see at least once. Plymouth Rock in Pilgrim Memorial State Park, Pilgrim Hall Museum, and the National Monument of the Forefathers are just a couple of examples of the many historical attractions that can be found in the town. However, if you’re looking to have a more immersive learning experience while visiting Plymouth, then you should stop by Plimoth Plantation, an expansive living history museum designed to showcase the history surrounding the Plymouth Colony. 

While the museum doesn’t date quite as far back as the pilgrim’s first arrival to Plymouth in 1620, it does sport a pretty impressive longevity—one that’s over seventy years long. What started in 1947 as two English cottages and a waterfront fort has now grown into a multi-venue site that features two stories: that of pilgrims and that of the Native Americans whose land would soon be taken from them. Today, Plimoth Plantation includes the Mayflower II, the English Village, the Wampanoag Homesite, the Hornblower Visitor Center, the Craft Center, the Maxwell and Nye Barns, and the Plimoth Grist Mill. 

Providence Walking Tour by Pinwheel Tourism 

📍 Providence 

Take a Historic Walking Tour Through Providence, Free of Charge!

1 Sabin Street | Downtown | 

Walking tours are a fun, engaging way to see a new city and learn more about its past—and as one of the oldest cities in the United States, Providence, Rhode Island, is certainly worth touring. Founded by a man who loves Providence too much to keep it to himself, Pinwheel Tourism invites visitors to take a guided walking tour that covers all of the city’s most notable neighborhoods and landmarks. And not only are the tours by Pinwheel Tourism comprehensive and enthusiastic, but they’re also free! 

The tour begins with an overview of Rhode Island’s state history, then commences on a two-hour walk through Providence’s history in chronological order, starting with its founding by Roger Williams in 1636 and continuing all the way to modern-day life in the city. A little less than two miles long, the walk through the city is extremely manageable and, for the most part, without hills. (As of right now, the tours are only offered Sunday mornings at 10 am during the months of May through October.)

Newport Cliff Walk

📍 Newport 

National Recreation Trail Along Newport’s Eastern Shoreline

1st Beach and Memorial Boulevard | Easton Bay |

Newport, Rhode Island, is located a little over two hours south of Boston and about 45 minutes south of Providence. Known as “The City By the Sea,” Newport sits on Aquidneck Island and boasts rich sailing history. The city is home to a number of Gilded Age mansions, perhaps the most popular of which is The Breakers by Ochre Point. But with scenic coastal views, historical points of interest, and countless photo ops, it’s not hard to see why the Newport Cliff Walk is one of the city’s most popular attractions. 

Designated as a National Recreation Trail in 1975, the Cliff Walk begins at Memorial Boulevard and Easton’s Beach and runs for about three-and-a-half miles to Bailey’s Beach and Bellevue Avenue. A combination of paved and unpaved trails, the Cliff Walk ranges from being easy to navigate in the beginning to being relatively difficult to navigate toward the end. Aside from some spectacular vantage points of the coastline, the Cliff Walk will also take you by several of the Newport mansions on Bellevue Avenue. Whether you do the whole thing or just a portion of it, the Cliff Walk is sure to make you fall in love with this charming Rhode Island city. 

Mystic Seaport Museum 

📍 Mystic (CT)

The Largest Maritime Museum in the United States

75 Greenmanville Avenue | Shipyard Point |

About two-and-a-half hours south of Boston and around three-and-a-half hours north of New York, Mystic, Connecticut, is a quaint town set on the edge of the Mystic River. Some of Mystic’s most noteworthy attractions include its Historic Downtown, the Mystic Museum of Art, the Denison Homestead Museum, and Olde Mistick Village, a collection of local shops and restaurants that are laid out to resemble a 17th-century village. The town’s most-visited destination, however, is probably the Mystic Seaport Museum, which is largely considered to be one of the world’s leading maritime museums. 

The Mystic Seaport Museum is an educational institution with exhibits and live demonstrations that will captivate visitors of all ages. Having steadily grown since its founding in 1929, the museum now covers 19 acres of land alongside the Mystic River and includes a collection of historic vessels, gardens, a planetarium, a preserved shipyard, and a recreated 19th-century New England village. One of the museum’s most prominent artifacts is the Charles W. Morgan, a wooden whaleship that initially launched in 1841, making it the oldest commercial ship that is still afloat in America. 

Rocky Neck State Park 

📍 East Lyme (CT)

Explore Coastal Connecticut in Its Most Natural State

244 W. Main Street | Niantic |

Rocky Neck State Park is about three hours north of New York, making it an ideal place to stop and stretch your legs before getting back in the car and hitting the road again. With over 700 acres of beaches, water, hiking trails, picnic areas, and wildlife, Rocky Neck is an eclectic blend of different types of geology and various forms of outdoor recreational activities. Camping, fishing, hiking, and swimming can all be enjoyed at the park, and amenities include a campground, bathrooms, food concessions, picnic tables, and a pavilion. 

Open from 8 am to sunset, this shoreside park can function as both a quick break or a prolonged stop before resuming the drive to New York. In the surrounding area of East Lyme, you’ll find several options in terms of food, including Illiano’s Grill; Smokey O’Grady’s; Flanders Donut, Bagel & Bake Shop; The Shack; and Rebeka Fresh Pasta

Studio 80 + Sculpture Grounds 

📍 Old Lyme (CT)

Outdoor Art Park with Over 100 Sculptures

80 Lyme Street | North Old Lyme |

Studio 80 + Sculpture Grounds is a quirky roadside attraction that’s sure to add a splash of creativity to your drive from Boston to New York. The four-and-a-half acres of green space hold more than 100 contemporary-style sculptures. This patchwork of art and nature belongs to the artist Gilbert Boro, who, in addition to working on the property, also lives there as well. Though his personal residence is, of course, closed to the public, Boro invites visitors to walk the grounds, appreciate the art, and even sit down for a nice picnic while enjoying the space. 

Boro’s studio, Studio 80, also welcomes visitors to take a look at the new creations that he and his studio assistants are working on. The second floor of the studio holds an art gallery where Boro’s small-scale works can be found. All of the works in the gallery are available for sale, so if you see something that you might be interested in, don’t be afraid to ask about the price! Throughout the year, the studio hosts a variety of events, and you can check out the events calendar online before your visit to see if anything special is happening while you’re in the area. 

PEZ Visitor Center

📍 Orange (CT)

Candy, Memorabilia, and Everything PEZ 

35 Prindle Hill Road | Orange |

The town of Orange, Connecticut is about two hours north of New York, and while it’s definitely a lot smaller than the Big Apple, if you’re a candy-lover, then you don’t want to pass up a chance to stop here—because it just so happens that Orange has the largest public collection of PEZ memorabilia in the entire world! That’s right, the PEZ Visitor Center is four thousand square feet of PEZ, the iconic dispensable candy that’s been in circulation since the 1920s. 

Open from 10 am to 5 pm Monday through Saturday (and from 12 pm to 5 pm on Sunday), the PEZ Visitor Center is right off of Interstate 95 when you take the Orange Exit (Exit 41). At the visitor center, you’ll find collector’s items like the world’s largest PEZ dispenser, as well as a wealth of brand history and trivia. Admission is $5 for adults and $4 for children under 12. Visits are self-guided, but if you have a group of 10 or more, you can schedule a candy-making demo two weeks prior to your visit. 

The Phillip Johnson Glass House 

📍 New Canaan (CT)

Historic House Museum with Extraordinary Architecture

798–856 Ponus Ridge Road | New Canaan |

The last stop on our list is around an hour-and-a-half from New York and can be found in the town of New Canaan, Connecticut, which was once the home of American architect Phillip Johnson. Though Johnson died in 2005, his legacy in New Canaan remains: the Glass House, designed by Johnson in 1949, is a National Trust Historic Site and is one of Johnson’s most famous works. Standing at 56 feet by 32 feet, the transparent building was inspired by Mies van der Rohe’s Farnsworth House in Chicago and continues to draw visitors from all over to the New Canaan area. 

There are several tours available for Johnson’s property, which, in addition to the Glass House, also includes painting and sculpture galleries, a pavilion, and several other structures by Johnson. It’s recommended that visitors purchase tickets in advance, as tours often sell out. Tour lengths range from one hour to three, and each package includes different levels of access to the buildings on the property. Whether or not you have a background in architecture, the stunning designs on Johnson’s property are sure to leave you amazed and impressed. 

New England Like You’ve Never Seen It Before 

From pilgrims and parks to museums and architecture, New England has destinations that will interest just about any kind of traveler. Massachusetts, Rhode Island, and Connecticut are all brimming with worthwhile detours that will make you glad to have taken the long way to New York. After all, it’s the City That Never Sleeps—it’s not like it’s going anywhere! Use the drive from Boston to New York to explore an area of the country that attracted colonizers in the first place and heavily contributed to the development of America as we know it. 

Albion Skeldon

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