10 Fun Stops For an Epic Boston To New York Road Trip (+ the Return New York to Boston Drive)

Sharing is caring!

I’ve spent another summer traipsing back and forth from Boston to New York thanks to visiting family and friends. Luckily, this trip is not a hardship because there are so many places along the way to make a Boston to New York (or New York to Boston) journey interesting. Although the NYC to Boston drive can be done in as little as 5 hours, if you don’t need to rush then a Boston and New York holiday with stops along the way is a great American road trip. You can drive NYC to Boston along the coast which will take you from New York to Connecticut, Rhode Island and then Masssachusetts. If you choose the inland route to travel between New York and Boston, you will pass through the same states except for Rhode Island. On the other hand, you will see more of rural New England on your New York and Boston trip.

Distance Between New York and Boston

The actual distance between Boston and New York if you go directly is only 215 miles (about 345 km). This trip can be done in 5 hours assuming you don’t hit traffic in New York, Hartford or Boston. I have a couple of married friends who did the NYC to Boston drive every weekend because one was working in New York and the other in graduate school in Boston. Not ideal but definitely workable for a short term period.

New York To Boston Road Trip


Getting from New York to Boston (and vice versa) can be done either along the coast or inland cutting through Western Massachusetts. On the coastal route, the main thoroughfare is the I-95 which is fairly uninspiring. The inland drive is longer (but not necessarily if the I-95 has traffic jams) but also prettier.

Drive NYC to Boston Along the Coast


When you drive New York to Boston along the coast, you will come across lots of charming towns and early American history.


New York To New Haven

Your first major stop after NYC on the way to Boston is the little city of New Haven in Connecticut. The distance from New York to New Haven is approximately 80 miles (129 km). Theoretically you can get from New York to New Haven by car in an hour and a half. If you hit traffic leaving New York though, it can be longer.

You Should Know:

New Haven CT is probably best known as the home of Yale University. In Boston, you will probably visit Harvard University, an arch-rival and fellow member of the Ivy League. Visiting Yale University will give you a chance to compare these two leading American educational institutions.

Ready to Mix Fitness and Sightseeing?  Take a fitness walking tour of the Yale University campus of New Haven.

Don’t Miss:

      • Yale University has scheduled campus tours or you can have a nose around by yourself.
      • There is a stellar art collection at the Yale Center for British Art and the Yale University Art Gallery.
      • Louis’ Lunch (263 Crown Street, New Haven CT 06511) claims to have invented that most American of foods in 1900 – the hamburger.  Louis’ Lunch is also supposed to be the oldest hamburger joint in the country AND among the first to serve steak sandwiches. (Note that the city of Philadelphia elevated the steak sandwich to perfection with the cheesesteak sandwich.)

Where To Stay:

Study at Yale is a cool boutique hotel located on the Yale University campus.

NB! Want to do some outlet shopping on the NYC to Boston drive? There are some smaller outlet malls along the I-95 in Connecticut. E.g., my kids consider the Pepperidge Farm outlet store at the Westbrook Outlet Mall an essential stop. In Massachusetts, a detour past Wrentham Village Premium Outlets is worth a pitstop if you are not going to pass by Woodbury Commons Premium Outlets (see below).
Pepperidge Farm outlet store cookies
You’ll find several outlet malls along the Boston to New York route which make excellent pit stops.

Mystic Connecticut

After you have had your fill of New Haven on the New York to Boston trip, your next stop will be Mystic Connecticut. New Haven to Mystic CT is an easy hour’s drive which covers 55 miles (89 km).

You Should Know: 

Despite Mystic’s myriad claims to historical relevance, Mystic Connecticut is probably best known for the 1988 film Mystic Pizza which launched Julia Roberts’ career as America’s Sweetheart.

Don’t Miss:

        • One of New England’s most visited destinations, Mystic Aquarium is dedicated to the education and research of marine life. It is a firm favourite with children and can get overrun with school trips.
        • Olde Mistick Village is located next door to Mystic Aquarium. It’s a shopping and restaurant destination set up as a cute little village.
        • Mystic Village is a living history museum which indoor and outdoor exhibits, including an actual whaling ship. Actors dressed in period costume explaining New England life in the 19th century.
        • Downtown Mystic is another charming New England town with a drawbridge and lots of cute stores.
        • Mystic Pizza actually serves up old-fashioned 1980’s pizza – bready crust and no fancy toppings like kale. Movie memorabilia abounds on the wall.
Old Mystic Village has restaurants and stores.
Between New York and Boston lies Mystic Connecticut which has many attractions like Olde Mystick Village with its restaurants and stores.

Where To Stay:

The Whaler’s Inn is a charming  boutique hotel in downtown Mystic. The 125 year old historic building has recently undergone another big renovation.

Make it easy on yourself! Check out these two tours:  

Newport Rhode Island

After Mystic Connecticut, make your way to another historical New England seaside town. Mystic Connecticut to Newport Rhode Island is another easy one hour drive covering 50 miles (80 km).

You Should Know:

Newport Rhode Island is famous for its sailing history prior to the American Revolution and as a major center of the slave trade. In the late 18th century, Newport became the favoured summer haunt of the American elite who built enormous mansions as summer cottages, some of which you can still tour today.

Don’t Miss:

      • Explore the Gilded Age mansions on Ocean Drive. The most popular mansion is The Breakers home to the enormously wealthy Vanderbilt family.
      • Check out the views along the 3.5 mile Cliff Walk
      • Visit the International Tennis Hall of Fame and the rest of downtown Newport

Where To Stay:

We are fans of the Vanderbilt Hotel which we found to be both elegant and family-friendly. The Vanderbilt Hotel is a luxury boutique hotel converted from a Vanderbilt mansion surplus to their needs.

A sign welcoming visitors to Massachusetts
The Boston to New York drive involves a long stretch in Massachusetts no matter whether you go the inland or coastal route.

Make it easy on yourself! Check out these two Newport Rhode Island tours:

Plimouth Plantation

As you drive NYC to Boston, the last stop on this road trip is Plimouth Plantation in Massachusetts  which tells the story Plymouth Colony established in the 17th century. English Pilgrims disembarked from the Mayflower to create a colony that would eventually grow to become a country. The drive from Newport Rhode Island to Plimouth Plantation takes an hour and 15 minutes and covers 60 miles (97 km).

You Should Know:

Plimouth Plantation is another  living history museum with indoor and outdoor exhibits. Actors bring the early years of the Puritan settlers to life.

Don’t Miss:

      • The Mayflower 2 which is a full-scale reproduction of the original one that brought the Pilgrims to the New World.
      • The 17th Century English Village established by the Pilgrims.
      • The 17th Century Wampanoag homestead who were the Native Americans who lived in the area when the Pilgrims arrived.

Plimouth Plantation to Boston

Your final drive from Plimouth Plantation to Boston takes 50 minutes and covers 43 miles (69 km). Traffic coming into Boston can be heavy so note that it can take longer.

Make it easy on yourself! Check out these two tours:

Boston to New York Drive – Inland

The Boston to New York drive inland takes you through bucolic New England countryside as well as more experiences with early American history.


Boston to Old Sturbridge Village

The first stop on your Boston to NYC drive is Old Sturbridge Village. The drive from Boston to Old Sturbridge Village takes an easy hour and covers 60 miles (97 km).

You Should Know:

Old Sturbridge Village is another  living history museum with indoor and outdoor exhibits. Actors bring a 19th century New England village to life.

Don’t Miss: Check and see if your visit coincides with Brimfield Antique Fair which bills itself as America’s oldest outdoor antiques market. Brimfield is a mecca for antiques dealers and buyers. Many people come from all over the nation to attend this market when it is on.

Where To Stay:

The Old Sturbridge Inn and Reeders Family Lodges are a good option near Old Sturbridge Village.

Old Sturbridge Village to Litchfield County Connecticut


After Sturbridge Massachusetts, you will wend your way through farmland from Massachusetts to Connecticut.

The drive from Old Sturbridge Village to Litchfield County in Connecticut is an hour and 40 minutes covering 81 miles (130 km).

You Should Know: Litchfield County is American rural beauty at its finest. The towns are full of white clapboard colonial homes and there are plenty of church spires piercing the sky. The landscape features rolling hills interspersed with vineyards and farms.

Don’t Miss:

      • If you are there for autumn foliage seasons, make sure you visit the little town of Kent which has been recognised as among the best for the foliage peeping.
      • Browse the many antique stores in the area.
      • Visit the Haight Brown Vineyard which is the state’s oldest winery.

Where To Stay:

Another Auberge Collection hotel like The Vanderbilt, the Mayflower Inn and Spa is located in the town of Washington, Connecticut. This luxury boutique hotel is also known for its excellent restaurants.

US Military Academy at West Point


From rural Connecticut, make your way to upstate New York. The US Military Academy at West Point lies just beyond the commuter suburbs of Westchester County. The drive from Litchfield County to West Point takes 2 hours and covers 77 miles (124 km).

You Should Know: A national landmark site, the US Military Academy at West Point trains officers for the US Army. West Point was decreed by President Thomas Jefferson in 1801.  In its long history, West Point has produced numerous Presidents, generals and medal of honour recipients.

The chapel with flags at West Point Military Academy
A NYC to Boston drive can take you through the US Military Academy at West Point.

Don’t Miss:

      • There are organised visits to the West Point Campus. All US citizens over the age of 17 have to produce photo ID. All foreign nationals must have a valid passport and visa.
      • The West Point Museum has a fascinating collection of American military-related exhibits.
      • The West Point cemetery is an add on to the tour. I thought it was very impressive and worth visiting.

Where To Stay:

Overlook on the Hudson is a small B&B which is located near West Point. In fact, both daughters of the owners married West Point graduates. The Overlook’s claim to fame is that it was the 1970’s home of Billy Joel. With views over the Hudson River, you can easily see how Billy Joel penned one of his most famous songs, New York State of Mind, here.

The Yale University campus
Any NYC to Boston drive will take you from New York to New Haven which is famous for Yale University.

Woodbury Commons Premium Outlet Shopping

Also in New York state, you will find some of the finest outlet shopping on the East Coast. The drive from West Point to Woodbury Commons Premium Outlets takes half an hour and covers 18 miles(20 km).

You Should Know: Woodbury Commons Premium Outlet Shopping is a super popular shopping mecca. Tourists take buses from New York City just to visit this outlet center which has the most designer stores of anywhere in the world (e.g, Balenciaga, Armani and Prada). There are also lots of other major outlets that are not high-end luxury names, such as Adidas and Gap.

Make sure you have comfortable walking shoes and are prepared to nab a bargain when you see it. Expect to see busloads of Chinese and Japanese tourists looking for brand names.


Woodbury Commons to New York City

Make it easy on yourself! Take a guided day tour from NYC to Woodbury Commons to avoid the drive.  

The drive from Woodbury Commons to New York City takes 1 hour and covers 55 km (89 km).

Getting To/From Boston and New York

Boston and New York are both very easy destinations for domestic flights in the USA and also for international flights. Logan International, Boston’s airport, is located very close to the city. Although John F. Kennedy International, LaGuardia Airport and Newark International, the three airports serving New York are either in an outer borough or New Jersey, both public and private transportation are plentiful and easy.

If you are an overseas visitor from one of the countries from which the USA allows a visa waiver, be sure to get your ESTA (Electronic System for Travel Authorisation) which is a visa waiver program. One of our UK friends got turned back from JFK because he didn’t have his ESTA. The USA put in these visa requirements for all foreign visitors after the 9/11 tragedy in order to better track who is entering and leaving the country.

Please also remember that you need to apply for ESTA no later than 72 hours before getting on your plane to the USA. It is super easy to do and can be done online. There is a fee for the ESTA (currently £29.95). An ESTA is valid for two years (or whenever your passport runs out). An ESTA can cover multiple visits to the USA with each visit lasting up to 90 days.



roadtrip from boston to nyc
There are so many places along the way to make a Boston to New York journey interesting.
You can drive NYC to Boston along the coast through Connecticut and Rhode Island, or
choose the inland route. Check out 10 fun stops for an epic Boston to New York road trip.
#roadtrip #newengland #nyc #boston
10 fun stops on a Boston to NYC road trip
A Boston and New York holiday with stops along the way is a great American road trip. Check out 10 fun stops for an epic Boston to New York road trip. #roadtrip #newengland #boston NY | New York | USA | United States America | Travel Destinations | Vacation | Off the Beaten Path | Bucket List | Wanderlust | Things to Do and See | Culture | Food | Tourism | Like a Local #travel #vacation #offthebeatenpath #bucketlist #wanderlust #NY #USA #America #UnitedStates #NewYork #NewYork

This site generates income via partnerships with carefully-curated travel and lifestyle brands and/or purchases made through links to them at no extra cost to you. More information may be found on our Disclosure Policy.

4 thoughts on “10 Fun Stops For an Epic Boston To New York Road Trip (+ the Return New York to Boston Drive)”

Leave a Comment

Your email address will not be published. Required fields are marked *