Feel like taking a break from your busy schedule? Want to experience a short road trip? Read our detailed guide on New York and Boston road trip itinerary.
If you’re a local staying in New England, you might have already experienced the journey from New York to Boston. Our itinerary is curated for those who haven’t yet explored the gems located between these two iconic cities.
You can take a trip to Boston from New York within four hours in standard terms. But, honestly, what’s the fun in that?
There are numerous attractions, landmarks, and iconic experiences waiting to be witnessed by travelers like you. And with the help of our New York to Boston road trip, we make it possible to discover these unique locations gloriously.
So, if you’re in the United States and looking to venture off on a journey covering the East Coast, we present this New York and Boston road trip. This itinerary is meant to showcase New England’s adoring beauty in the best way possible.
Let’s get started!
Overview of New York to Boston Road Trip
The itinerary designed for this New York and Boston road trip is for 7 days. The total journey is around 330-miles, taking approximately 6hr 18minutes (an indicative number based on the time of writing). The route taken for this specific road trip is via I-95N, but you can take alternative ways depending on the traffic and travel time.
We wanted to create a simple yet adventurous journey covering central locations falling between New York and Boston. The idea was to connect these locations and make an epic short trip for travelers who only have a week’s vacation.
Any age group can take this New York and Boston road trip, as we have not included strenuous or challenging activities. Moreover, we have included only those particular stops or intervals which deem necessary to visit during your trip. This will surely elevate your experience of driving from NYC to Boston.
This New York to Boston road trip can be done in reverse order. Suppose you had to do – Boston to New York road trip – the same route given in our below map will apply. Alternatively, you can approach Interstate 90 West from Boston to take the fastest way to NYC.
New York to Boston Road Trip Schedule
Day 1: New York City
Day 2: New York City – New Haven
Day 3: New Haven – Essex, CT
Day 4: Essex – Newport, RI
Day 5: Newport – Cape Cod
Day 6: Cape Cod – Boston
Day 7: Boston (Departure)
Map of New York and Boston Itinerary
Check this New York to Boston drive map, detailing the exact route and locations. To get an interactive version of the below map, click here.
Detailed New York to Boston Road Trip
Day 1: New York City
Let’s get started with our New York to Boston road trip by exploring the significant sights of NYC.
New York City is a playground for tourists to indulge in a whirlwind of activities. Famous for its incredible nightlife, cafes & restaurants, pub scenes, gastronomy, museums & art, and world-class theatre productions, New York boasts all of its attractions & activities to entice tourists worldwide.
What makes New York so unique is its varied experiences. You could spend an entire week in NYC visiting many of its landmarks & sights. Forget about a week; you could spend a whole day in Central Park itself, relaxing & unwinding around its gardens, lakes, and carousel.
With so much to see and do around, it’s overwhelming for a first-time traveller to explore New York City. Since we are on our road trip to Boston, we won’t be spending much time in the city. We recommend choosing one neighbourhood out of Soho, Midtown East, Theatre District, and Lower Manhattan to explore.
Below we have recommended a few places within the Lower Manhattan region. Check this page to see what NYC’s other neighbourhoods have in store.
Visit the Times Square
Times Square is not only the famous landmark of New York but also the liveliest area of all neighbourhoods. When you visit Times Square, it’ll always be packed with tourists, especially during the holiday season.
What makes Times Square so unique is its atmosphere. The streets are illuminated with giant billboards, Broadway theatres, fantastic coffee shops, and a large chain of restaurants. Moreover, a walk around the street across Times Square will introduce you to a paradisical world of fashion stores & boutiques.
The High Line
The High Line is known to provide some of NYC’s best surrounding views. It’s an elevated park that starts from Hudson Yards and stretches up to the northern edge of Chelsea.
You can stroll the entire pathway starting from one end to the other, exploring wildflowers, greenery, and outdoor art installations in addition to the views.
Note: The High Line can get overcrowded on a bright sunny day, and it isn’t a pleasant experience, especially if you’re planning to walk along the park. To avoid them, try arriving early in the morning.
Take a Ferry to the Statue of Liberty
Undoubtedly, the Statue of Liberty is America’s most famous landmark. The place is listed on every NYC tourist itinerary, and thus we thought of including it in our New York to Boston road trip.
To tour the Statue of Liberty, we recommend taking the Staten Island ferry to Liberty Island. The Ferry leaves from the Whitehall Terminal and reaches the other point, i.e., St. George Terminal. It approx takes 25-minutes for each way ride.
Optional Tours in New York City
If time permits, we recommend choosing a few attractions out of the below list. You can either do a self-exploration of these places or book guided tours to manage your schedule well.
- Battery Park
- Marvel at Oculus
- Visit the 9/11 Memorial and Museum
- Explore the Trinity Church
- Visit the One World Trade Centre
Day 2: New York City – New Haven
Today we leave New York City and make our way to New Haven county.
New Haven is one of the most under-rated stops in New England, and it doesn’t get mentioned in most New York to Boston road trips, but it still is a worth exploring place.
New Haven boasts a fantastic dining scene here and numerous historical touchpoints. Tons of music shows, concerts, and events level up New Haven’s cultural essence every year. In addition to positive experiences, there are many sight-seeing points too – which you should visit during your trip to Boston.
Check the below-recommended activities which you can explore in New Haven –
Yale University
Yale University has been a pride of New Haven county, and it’s not only an essential landmark from a historical standpoint but also the most visited place in New Haven. During your stop, you can opt to take a guided tour of the university to learn more about its campus and history.
Most of the sections and pillars were built by well-known architects in the form of gothic architecture. Many of its rooms, halls, & libraries hold the same design – making it enjoyable to tour the university. Other places to see within the campus include the Center for British Art, the Art Gallery, the Beinecke Rare Book and Manuscript Library, and the Peabody Museum.
You can also enjoy the complimentary morning tours led by campus students.
Connecticut Science Center
If you’re a fan of science exhibits, head to Connecticut Science Centre to explore 150+ displays of practical projects. These collections are mainly on the topics of science, covering space, biology, and other scientific discovery. The idea of this establishment is to engage children to proactively learn, inspire and develop their brainwork in these related fields.
Moreover, even parents find it interesting to engage in many of its live activities hosted within the center. The Science Alley and an Engineering Lab are its two most important spaces, showcasing live demonstrations of complex world problems.
So if you’re on a road trip to Boston with kids, the Connecticut Science Centre is undoubtedly the right place to stop by.
Experience the Summer Jazz Festival
New Haven sets up different venues featuring musical shows and concerts throughout the summer. This is meant to celebrate the diversity of jazz music and culture in the county.
So if you’re in town and come across any of these venues – make sure to attend one. Most institutions like the Neighborhood Music School, the New Haven Museum, and the Pardee-Morris House host jazz concerts around New Haven. Café Nine and Café a Vin also host popular shows for a limited time.
You can check the dates here for upcoming events.
Other than the experiences listed above, there’s a lot to do around New Haven county. As we mentioned before, the town is known to provide excellent gastronomy scenes to its visitors. Back in 2014, it was coined the “Best Foodie City in the US.” This award lets you explore different restaurants, cafes, and pubs in New Haven.
Overnight stay at New Haven.
Day 3: Essex, CT
The next stop on our New York to Boston road trip is the Essex.
The quaint town of Essex is only a 45-minute drive away from New Haven. Before arriving directly in Essex, there are multiple points along the Connecticut Coast to admire. Hence, ensure that you leave early in the morning to spend some time at each suggested location.
The first place to stop by is Norwalk. Known for its historic oyster industry, the place has special ties with its harbors and islands located offshore. It’s a great place for New Yorkers, who often hit Norwalk during the summers to take a cruise or boat ride.
When you arrive in Norwalk, take a small boat trip to the nearby Sheffield Island lighthouse. It will approx take you 45-minutes to get past the tiny islands located near Norwalk. The experts on the boat will brief you on the surrounding attractions located off the Long Island Sound. After you reach Sheffield Island, visit the Sheffield Lighthouse, established in 1868, or you can spend time strolling, picnicking, or exploring its walking trails.
Alternatively, you can explore the below two attractions of Norwalk –
The Maritime Aquarium
The Maritime Aquarium is one of Norwalk’s most essential attractions. It houses more than 2,700 aquatic species spread across 75 different marine life exhibits. As you journey through the entire center, you’ll come across harbor seals, river otters, baby sharks, turtles, and jellyfish.
This aquarium has touch tanks that bank other marine life, including stingrays, starfish, and nurse sharks. Moreover, the place also has an IMAX theatre to offer visitors a visual display of marine life in action. With the surround sound and other lighting effects, the experience of watching these aquatic species is theatrical.
Visit SoNo
SoNo (South Norwalk) is the place to experience the vibrant neighborhood, arts, culture, shopping, and entertainment. The locals here are energetic as ever, guiding you to the location’s best-hidden spots and attractions.
The culinary scene in South Norwalk is incredible. With eateries and street stalls serving different cuisines, you can hog onto items that you may have never tried in life. When you’re in this neighborhood, it doesn’t matter what food preference you have – you ought to come across shops selling different items, including fish tacos, baklava, grilled cheeseburgers, sandwiches, sushi, and clam chowder.
After a brief exploration of Norwalk and its attractions, head to the town of Essex to spend a night. If time permits and your schedule fits right, you can always spend an extra day at Essex to explore its unique tourist spots. These include taking a ride on Essex Steam Train, cruising on the Connecticut River, exploring Gillette Castle, and many more sights.
Overnight at Essex.
Day 4: Newport, RI
Today, we depart early morning to make our way toward Newport, RI.
Newport seems like a different world altogether, and it’s a place where you can easily spend a long weekend discovering essential landmarks and historic sites. Of course, we can’t cover everything in this New York and Boston road trip – but we’ve suggested a few attractions that you should check out during your drive to Newport.
The Ocean Drive
With all the journey you’ve done so far to reach Newport, nothing can beat the experience of driving the 10-mile Ocean Drive stretch. No matter how many times you visit this place, the downright beauty of the coastal road will never fail to amaze you.
Once you reach Newport, unwind down at a cafe and grab some breakfast to rejuvenate yourself. After you’re settled in, start your Ocean Drive journey off the historic Bellevue Avenu (see the location here). Head straight and keep following the signs for Ocean Drive.
You’ll be greeted with Newport’s notable landmarks, including Fort Adams State Park, the Museum of Yachting, Sail Newport, and the Castle Hill Inn & Resort. The best part about the entire journey is seeing many beautiful homes, summer yachts, waterfront cafes, and spectacular views.
Further towards the south, you’ll locate Brenton Point, State Park. There’s free parking here, so you can park your car and enjoy the stunning ocean views for as long as you can.
As you continue your drive past Brenton Park, you’ll get the best close-up views of the Atlantic Ocean. Many private exclusive beaches, Hazard’s and Bailey’s, are not open to the public. But, you can unwind at Gooseberry beach to claim fantastic sunset views.
Discover Newport’s Mansions
The historic mansions located in Newport showcase a breath-taking charm of history, wealth, and architecture. Many of the grand villas belong to America’s most influential men and women. These mansions are their “summer cottages,” which get opened for guided tours to the public.
There are many mansions based in Newport, but these are the ones you should check out during your exploration –
- Rosecliff
- Marble House
- The Breakers
- Rough Point
- Chateau-sur-Mer
The Breakers and the Elms have the most impressive structure, and it’s also the busiest mansions of all – especially during the summers. These two mansions are open during the winter months to keep up with tours. Tickets will have to be purchased in advance to avoid full occupancy. To check the calendar of these mansions, visit this page.
To get more details on Newport’s mansions & guided tours, explore this website.
Overnight at Newport.
Day 5: Newport – Cape Cod
It’s finally time to leave Newport to make our way to Cape Cod, Massachusetts.
Cape Cod is a popular summertime destination for tourists. With an expansive coastline of 40-miles, the place has become New England’s prime beach location. It has everything you need – from quaint villages and seafood shacks to ocean viewpoints and abandoned lighthouses.
While you’re here, Cape Cod will introduce you to endless touristic opportunities. While the whale watching tour steals the limelight, its long bike rides and theatrical music show add even more thrill to your perfect stay in Cape Cod.
We are sticking to a single overnight stay in Cape Cod for our New York to Boston road trip. However, feel free to extend your stay to discover more attractions & local experiences.
Below are some of the recommended activities to do in Cape Cod –
Cape Cod Rail Trail
When you only have a single night’s stay at Cape Cod, you should make it a point to discover the Cape Cod Rail Trail. The trail is approx 27-miles long, making it entirely possible to cover the stretch in a day. The flat surface makes it easy for all grade-level bikers to ride across the trail. Every summer, many recreational cyclists arrive here to take on the adventure.
Since Cape Cod is one of the best bike trails in New England, there’s no shortage of restaurants housing the entire pathway. The Yarmouth-South Dennis section, in particular, has a great lineup of classic restaurants and cafes serving multi-cuisine food. Love home-made Italian food? Head to Gerardi’s Cafe located in South Yarmouth. Craving for continental and seafood? Make your way to Jason’s Tavern at South Dennis. There are plenty more along the trail, which you can find here.
Note: There are currently two rental bike shops in Cape Cod. One is Brewster Bike, where you can rent or purchase hybrid trek bikes; the other is the Rail Trail Bike & Kayak Shop, located on the Cape Cod Rail Trail itself. You can rent all biking-related accessories, equipment, and items.
Cape Cod National Seashore
Late in the afternoon, head to the eastern shore of Cape Cod to explore fantastic beaches, protective wildlife, and unique hiking trails. The vast 40-mile stretch features New England’s prime beaches, including Marconi Beach, Nauset Beach, and Herring Cove beach.
You can even stop by the visitors center to learn more about the region’s protective area and its shoreline history.
Wellfleet Drive-In
If you’re wondering how to spend your late evening at Cape Cod, then fret not – head to Wellfleet Drive-In to take a break from all the hustle you’ve been doing so far. With a playground next to the driving lot and a mini-golf course – Wellfleet Drive-In is a perfect family spot to relax, unwind and re-energize.
Moreover, the retro theatre experience is genuinely nostalgic. Your kids might not get the importance of this vibe; however, for you (parents), this is something you can’t miss.
Note: Tickets for adults and kids cost $15 and $10, respectively. Credit cards are not accepted here, so ensure you have some cash in hand. Furthermore, try to arrive at the box office around 7 pm to get a good seating spot.
Overnight at Cape Cod.
Day 6: Cape Cod – Boston
It’s time to finally hit the last stop of the New York and Boston road trip. We recommend you leave early in the morning to make sure you have ample time to relax in Boston.
Boston thrives on art, culture, history, and nightlife. There’s so much to do in the city that you can spare a separate itinerary for Boston. It’s also one of the significant locations in the history of the United States. It is where Boston Tea Party took place, which revolutionized the history of America.
But, there’s more to Boston than digging deeper into its history. Its vibrancy spreads across the city, indulging tourists in engaging in activities and events. The cutting-edge restaurants, unique performances, harbor cruise, and endless shopping opportunities make Boston a must-visit place in the United States.
We recommend the below activities to do in Boston –
The Freedom Trail
Undoubtedly, the Freedom Trail is one of Boston’s prime tourist spots. It’s a 2.5-mile-long stretch that takes you across 16 historic sites in Boston. They are well interconnected, making you traverse between each of these attractions smoothly.
Start your Freedom Trail exploration at the Boston Common Visitor Information Center and continue down the path to visit King’s Chapel, Old State House, Massachusetts State House, Faneuil Hall, Old Corner Bookstore, Park Street Church, and Old North Church. For a detailed list, visit this page.
There are cute cafes, shops, museums, graveyards to discover, and these big names. If you ever feel tired or need a break, you can always stop for a coffee break. Moreover, the Freedom Trail is an excellent way to start your trip to Boston, and it’s instead a brief-exploration tour of famous attractions.
Isabella Stewart Gardner Museum
When you visit museums, you often appreciate the artwork & displays stored inside. But the Isabella Stewart Gardner Museum will change your mindset on how you look at museums. The building is just as beautiful as the artwork stored inside.
Isabella Stewart Gardner was an admirer of the art, and through her inspiration, she created this fabulous museum we see in Boston today. The whole place looks filled with gardens and small trees lined with patios, textiles, and archways. If you’re a collector of rare books, you’ll love discovering the old books preserved here.
Even if you’re not an admirer of the art, you’ll be fascinated with what’s stored inside the Isabella museum.
Relax at Boston Common
The city of Boston has its own Central Park in the form of Bostom Common. It’s one of the oldest public parks in America, housing all sorts of recreational activities & events.
It doesn’t matter in which season you travel, as Boston Common gives different experiences year-round. During winters, you can ice-skate on frog ponds, go sledding or snowboarding, while during summers, you can work out your body on tennis or basketball courts.
No matter what, it’s a perfect family place to stroll, picnic, and relax.
Visit the Boston Harbor
Boston Harbor carries a historical significance in the events in America’s history. While history remains intact, modern urbanization has brought a lively cultural essence to the place. Today, the Boston Harbor houses numerous museums, shipyards, landmarks, restaurants & cafes.
Furthermore, elevate your experience by taking a boat ride to the islands of Massachusetts. If not, pedal down the streets on a bike to tour galleries, shops, and quirky stalls selling unique souvenirs.
Optional Activities in Boston
If time permits, you can visit Encore, Boston’s mega-casino resort. This massive 210,000-sqft space includes 15+ restaurants, indoor & outdoor events, and plenty more. You can either go big, try your luck at the casino, or indulge in activities to admire the indoor beauty of Encore.
One of the fun things to do in Boston is go whale-watching. The surrounding waters of the harbor area make it ideal for spotting whales in their natural habitat. You can check these wonderful guided tours for more details.
Watch a game at Fenway Park. If you’re a baseball fan, surely make it a point to visit the Fenway Park stadium. It is known for its limited seating, precisely the same in 1912. Yes, it never got expanded, and it still offers the best close-up views of your favorite pitchers and batters.
Overnight in Boston.
Day 7: Boston
We are making the end of our epic New York to Boston road trip. You can further extend this road trip to other places beyond Boston or make modifications to adjust a couple of nights listed in this itinerary.
General FAQs for New York to Boston Road Trip
When is the best time to visit New York and Boston?
New York is instead the busiest place than Boston. Since these cities are year-round destinations, tourist places and landmarks are always at their peak. However, to ensure you have a pleasant experience, we recommend making a journey between April to June or September to November. Both the periods will offer mild temperatures and slightly thinner crowds.
How far is New York City to Boston?
If you were to travel from New York to Boston directly, it would approx take 3hr 45minutes (215 miles). Considering heavy traffic, the journey can take between 4.5 and 5 hours. However, regarding our New York to Boston road trip, we are stopping at multiple places/stops, covering an entire journey of 6hr 18minutes (330 miles).
What is the best route from NYC to Boston?
The most direct route to travel from NYC to Boston is Connecticut on I-84 E to I-90 E in Massachusetts. The road passes through the busy towns of New Haven and Connecticut, making it difficult during rush hours.
What are the other alternative sights to explore on our New York and Boston road trip?
Check this page to explore optional tours and activities for our New York to Boston road trip. The catalogue of guided tours will help you select the best exercises for this road trip.
Where to stay in New York and Boston?
To explore accommodation in New York and Boston, we recommend checking Tripadvisor. They provide the best listings at affordable rates (depending on the category).
Further Readings & Resources
New York City – 20 Free Things to Do in NYC: Discover the Best of New York
New York in Winter – 10 Best Things to Do In NYC at Christmas
Long Island, NY – Best Things to Do On Long Island in the Winter
Other American Itineraries
California – 10 Day California Road Trip: One Epic California Itinerary
Alaska – 10 Day Alaska Itinerary: Kenai & Denali Road Trip
Yellowstone – Yellowstone Itinerary: How to Spend an Ideal Time in Yellowstone
