20 Places To Visit On A Boston to New York Road Trip

Stretching over 230 miles (370 km), a Boston to New York road trip is a relatively short trip that sees travellers pass through several New England states, such as Massachusetts, Rhode Island and Connecticut, before ending epically in the heart of Manhattan. The fastest route takes 3 hr 50 min (215.0 mi) driving along the I-90 W, but with so many lovely towns and historical attractions to explore, you’ll enjoy taking a slower trip. 

From charming colonial towns to cities home to the most prestigious universities in the world to the witch trials of Salem and the birthplace of two US presidents in Quincy, there’s so much to take in and experience between these two influential cities. Here’s what to see on a Boston to New York road trip. 

20 Places To Visit On A Boston to New York Road Trip

Around Boston

1- Freedom Trail, Massachusetts

The Freedom Trail is a 2.5-mile-long (4 km) walkable tourist attraction that connects 16 of Boston’s best historic landmarks for visitors to learn about.

Whisking you through more than 250 years of history, Boston created the trail in 1951 to celebrate and preserve the city’s most iconic buildings and institutions.

The trail recounts Boston’s rich history from the American Revolution to today through various historic churches, museums, parks and even a ship.

Over 4 million people hike the Freedom Trail annually, making it one of Boston’s best free-to-do activities.

2- Harvard University, Massachusetts

Established by John Harvard, a Puritan clergyman, in 1636, Harvard University is a private Ivy League research university world-renowned for its academia and one of the most prestigious colleges in the world.

Harvard’s 10 faculties are spread out across three distinct campuses throughout Boston proper, with the main campus being in Cambridge, just north of Downtown Boston.

Harvard’s 209-acre (85 ha) Cambridge campus features several impressive landmarks to see, including Harvard Square, University Hall and Memorial Hall, making it a fascinating road trip destination to stop at before continuing your journey to New York.

Harvard University is in Cambridge, Massachusetts. 

3- Salem, Massachusetts

Before heading south, it’s worth taking a short detour to the north to visit Salem. 

Salem, Massachusetts, was placed firmly on the proverbial map when it became ground zero for the infamous Salem Witch Trials of the late 1600s.

Mass hysteria broke out among the English colonists in the area when several inhabitants were accused of witchcraft, leading to the execution of 19 adults and children rumoured to be witches.

The tragic event forever shaped Salem’s culture, with many tourists visiting Salem every year to learn more about the trails and the events that led up to them.

Today, Salem is a trendy tourist destination with various attractions, such as the Peabody Essex Museum and the Salem Witch Trials Memorial.

For a visit like no other, stop by this sleepy town just north of Boston during Halloween, when Salem’s autumn colours and spooky history combine to create a magical atmosphere.

Salem is 25 miles (40 km) from Boston and about 40 minute by road. 

Also read:

• 20 Things To Do In Boston At Night
• 20 Day Trips From Boston
• 21 Boston Landmarks
• 20 Landmarks In Massachusetts
• 20 Beaches In Massachusetts
• 18 National Parks In Massachusetts
• 7 Things To Do In Cape Ann
• 20 Things To Do In Worcester MA
• 20 Things To Do In Springfield MA
• 20 Things To Do In Salem MA
• Where To Stay In Boston
• 20 Best Boston Museums
• 21 State Parks In Massachusetts
• Boston in Winter
• 15 Things Massachusetts Is Famous For
• 15 Things Boston Is Famous For

Route 1 – The Coast Route

4- Quincy, Massachusetts

South of Downtown Boston, Quincy is a small Massachusetts coastal city famous for being the birthplace of former US Presidents John Adams and John Quincy Adams.

Quincy was also the birthplace of John Hancock, the first person to sign the Declaration of Independence, and was where America’s first commercial railroad and Dunkin’ Donuts store were established.

A city of many firsts, Quincy is a major historic town that’s amazing to stop at as you go further south towards Plymouth and Rhode Island.

Quincy is 11.6 miles (19 km) from Boston and around a 25-minute drive.

5- Plimoth Patuxet, Massachusetts

A living museum, the Plimoth Patuxet in Plymouth, Massachusetts, is a significant historical site that recounts the tales of the region’s English Pilgrims and the native Patuxet People.

The venue features several important landmarks and attractions for visitors and history buffs to see, including the Mayflower II, a reconstructed 17th-Century English Village, and a Patuxet Homesite.

A must-visit place in Massachusetts to better understand the region’s rich past, the Plimoth Patuxet is a fascinating place to plan a history-packed road trip stop.

Plimoth Patuxet is 34 miles (55 km) from Quincy and about a 40-minute drive. 

6- Providence, Rhode Island

Home to numerous public parks, a vibrant performing arts scene and several fascinating museums, Providence is among the most influential cities in New England.

Providence provides road trippers with a healthy balance of old and new to experience across various historical and contemporary attractions, such as the John Brown House Museum, the annual WaterFire festival, and the main campus of Brown University.

Providence is 57 miles (92 km) from Plimoth Patuxet and about a 1hr 10 min drive. 

Recommended tour: Downcity Providence Food Tour

7- International Tennis Hall of Fame, Rhode Island

Established in 1986, this former run-down casino turned tennis museum honours the biggest tennis stars throughout the history of this popular global sport.

Several legendary tennis players are inductees of the tennis hall of fame, including Andre Agassi, Arthur Ashe, Rod Laver and Martina Hingis, with notable former players added yearly.

Tennis-inspired art and interactive displays honouring the history of tennis are just some of the cool and unique things to see at the museum, now a National Historic Landmark.

A perfect destination for an afternoon road trip pit stop, the museum will keep even those who aren’t sports fans entertained, with the venue being one of the premier sightseeing points in Newport.

The International Tennis Hall of Fame is 34 miles (55 km) from Providence and a 50-minute drive. 

8- Cliff Walk and The Breakers, Rhode Island

One of the best walking spots on the East Coast, the Cliff Walk in Newport is a must-visit if you enjoy relaxed strolls alongside the ocean.

With many splendid mansions lining the walk, strollers get to view some of the most impressive homes in the country despite many failed attempts by their owners to block the path to the public.

The Breakers is one of those flashy mansions lining the Cliff Walk and one of Rhode Island’s most famous historic mansions.

Built by Cornelius Vanderbilt in 1895 for his immediate family, this exquisite 70-room Italian Renaissance-style manor is a National Historic Landmark and a place that visitors need to see to believe.

You can easily visit the International Tennis Hall of Fame, visit The Breakers and do the Cliff Walk in one day, making this part of Rhode Island a great place to stop between Boston and New York.

Recommended: Scenic Newport, RI Self-Driving Audio Tour.

9- Mystic, Connecticut

Mystic is your typical Connecticut coastal city, complete with romantic beaches, charming streets, and a rich maritime past in Connecticut’s southeast corner near the Rhode Island state border.

The city was first established in the 17th century and has stood at the centre of the Northeast’s shipbuilding industry, with over 600 ships built in Mystic throughout the city’s history.

While Mystic is no longer an important shipbuilding site, the modern city is home to numerous family-friendly attractions and landmarks such as the Mystic Aquarium, the Olde Mistick Village and the Mystic Seaport.

Rich in New England history and culture, Mystic is a charming coastal paradise you will love exploring when road-tripping between Boston and New York.

Mystic is 50 miles (80 km) from the Cliff Walk and a 1 hr 10-minute drive. 

Recommended: Mystic Seaport Museum Adventure.

10- Yale University, Connecticut

Classy, sophisticated, and the ying to Harvard’s yang, Yale University in New Haven, Connecticut, is a private Ivy League research university and one of the world’s most prestigious. 

Yale was established in 1701 by the Connecticut Colony’s Congregationalist clergy and is the third-oldest higher education institution in the United States.

Many Nobel Prize winners and presidents have rolled through the doors of Yale.

The university’s beautiful tree-lined campus makes it a historic and scenic destination as you pass through peaceful Connecticut.

Yale University is a Connecticut landmark 56 miles (90 km) from Mystic and a 1-hour drive. From Yale, it’s a 1.5-hour drive to Central Park. 

Route 2 – Inland Detour

An inland detour from Boston to Northampton to Springfield and Hartford is another route that will get you to New York. Here are some highlights. 

11- Northampton, Massachusetts

Known throughout New England for its academic and artistic prowess, Northampton is a quaint little city in western Massachusetts within two hours of Downtown Boston.

Northampton is often regarded as America’s most alternative mid-sized city due to Northampton’s reputation as a beacon for counterculture movements.

Quirky for some and forward-thinking for others, Northampton offers many attractions and landmarks catering to visitors of all interests and backgrounds.

The Smith College Museum of Art, the scenic Norwottuck Rail Trail and the historic Academy of Music Theatre are just some of Northampton’s many fascinating things to do, so be sure to plan a visit to this unique New England destination.

Northampton is 104 miles (167 km) from Boston and about a 2-hour drive. 

12- Hartford, Connecticut

The capital of Connecticut and the self-proclaimed ‘Insurance Capital of the World’, Hartford is a charming city conveniently situated roughly halfway between Boston and New York City.

Home to many scenic public parks, historical landmarks and unique cultural institutions, Hartford is a lovely city to plan a visit with something for everyone to do.

Hartford is packed with cool sights, from the historic Mark Twain House & Museum to the grandiose Connecticut State Capitol.

Hartford is 45 miles (73 km) from Northampton and less than a 1-hour drive. 

13- Litchfield, Connecticut

Settled by Europeans in the early 18th century, Litchfield has retained its typical New England 1700s feel.

Known initially as Bantam, the town has several attractions and landmarks worth seeing, including Connecticut’s biggest natural lake.

You might be surprised to learn that the picturesque town was a weapons depot during the Revolutionary War.

History, culture and nature in and around Litchfield make it a popular road trip stopping point in Connecticut and a great place to spend a day or two.

Litchfield is 32 miles (52 km) from Hartford and about 45 minutes of driving. 

14- Culinary Institute of America, New York

Situated in Hyde Park and overlooking the scenic Hudson River, the Culinary Institute of America is a culinary school specialising in teaching baking, culinary and pastry arts.

Foodies will love stopping here to see where many famous chefs have perfected their trade at the CIA since its founding in 1946.

The school was the first culinary arts college in America at its founding.

It also has a scenic campus and is home to four restaurants serving meals made by the institution’s students. 

The Culinary Institute of America is at 1946 Campus Dr, Hyde Park, NY 12538, 54 miles (87 km) from Litchfield and around 1 hr 16 minutes on the road. 

15- Storm King Art Center, New York

The Storm King Art Center is an open-air museum in upstate New York with grounds spread over 500 acres (202 ha).

Featuring ever-changing exhibits and displays, the centre was formed in 1960 to protect the scenic forests, hills and meadows of the Storm King Mountains.

Conveniently located just an hour’s drive north of Manhattan, the centre is famous for its fantastic art exhibitions, which often feature paintings and sculptures from the collections of art galleries worldwide.

The centre’s stunning landscapes perfectly compliments the art displays, making it a highly-rated and globally recognised cultural institution that’s always a great destination to stop at on any Boston to New York road trip.

The Storm King Art Center is at 1 Museum Rd, New Windsor, NY, 27 miles from Hyde Park and about a 42-minute drive. 

16- US Military Academy at West Point, New York

Most people know it as ‘West Point’, and its claim to fame is it’s the oldest service academy in the USA. 

Founded by Thomas Jefferson in 1802, the academy educates cadets who plan on enlisting in the military after their time at West Point.

The academy is a dedicated National Historic Landmark.

Situated in New York’s scenic Hudson Valley, West Point’s stunning Norma-style architecture, fascinating history, and cultural importance make the academy a popular tourist attraction.

There’s a visitor’s centre and the oldest military museum in America for visitors to learn more about military history. 

US Military Academy at West Point is at 606 Thayer Rd, West Point, NY. It’s 10 miles (16km) from the Storm King Art Center.  

17- Kykuit Estate, New York

The Kykuit Estate, or the John D. Rockefeller Estate, is a magnificent 250-acre (101 ha) estate built for the Rockefeller family, one of America’s most influential families, in 1913.

Featuring over 40 rooms, the estate is a dedicated National Historic Landmark and is open to the public for tours.

About 25 miles (40 km) north of New York City, the estate is easy to reach and is one of the most stunning historic landmarks in the Hudson Valley.

Kykuit, the Rockefeller Estate is 28 miles (45 km) from Westpoint at 381 N Broadway, Sleepy Hollow, NY 10591. The driving time from Westpoint is about 40 minutes. 

18- Sleepy Hollow, New York

In New York’s Westchester County on the banks of the Hudson River, Sleepy Hollow, once known as North Tarrytown, was the setting for the eerie 1820 short story by Washington Irving titled “The Legend of Sleepy Hollow”.

The town’s name was formally changed to Sleepy Hollow in 1996 to celebrate the novel that put the town on the map.

Today, Modern-day Sleepy Hollow treats visitors to a laundry list of fun and unique things to do, ranging from the Old Dutch Church, which inspired Irving’s tale ‘Headless Horseman’, to the scenic Rockefeller State Park Preserve and its stunning wildlife.

New York

19- Central Park, New York

The world-famous Central Park was established in 1858 to provide a rapidly growing New York City with a much-needed recreational area to retreat to.

Originally intended to bring a slice of the countryside to busy Manhattan, Central Park still provides city slickers with expansive greenery to enjoy away from the noisy and overcrowded streets of the Big Apple.

More than 42 million people stop by the park annually, making it the most visited public park in the USA, and wandering around the park is one of the top things to do in New York.

Meticulously designed by notable public park planners Frederick Law Olmsted and Calvert Vaux, Central Park is home to several amazing things to enjoy and serves as the perfect place to end your once-in-a-lifetime road trip through America’s Northeast corner.

Treat yourself to a Standard Central Park Horse Carriage Ride (Long Loop – 45 Minutes)

20- Empire State Building, New York

A true icon of the Big Apple’s world-famous skyline, the 102-story Art Deco-style Empire State Building is a soaring American landmark that took just one year to finish.

Officially opened to the public in 1931, the structure held the title of the world’s tallest building for nearly four decades when the World Trade Center eclipsed it in 1970.

The Empire State Building is in Midtown, Manhattan, and attracts over 4 million visitors annually thanks to its high observation decks and representation in pop culture.

Not only is this iconic skyscraper one of New York City’s must-visit landmarks, but its pioneering design and top-notch vantage points make it a truly unmissable road trip attraction to stop by as you near the end of your Boston to New York journey.

The Empire State Building is 30 miles (48 km) from Sleepy Hollow. Driving time will depend on traffic conditions. Skip the line and book your entry ticket here.

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