Road Trip

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Boston to New York City: New England Road Trip!

Explore the ultimate New England road trip from Boston to NYC! Tips on scenic stops, best seasons, and essential eats for travelers. Ideal for a weekend escape.

Tobi Miles
July 1, 2022
Boston to New York City: New England Road Trip!

Boston to New York City Road Trip - Driving from Boston to New York City, is a fantastic journey of 215 miles, through Connecticut via I-90 W. If you drive directly there it will take you around 4 hours.

However, if you have a few days I would definitely suggest stopping of at a few sweet spots, along your road trip. Such as Bristol & New haven Connecticut, or even drive down to the rhode island coast for some seafood and scenery.

This is the perfect road trip for a weekend getaway, with your partner, group of friends or even solo!

Best Time of Year to Drive to New York City?

Driving from Boston to New York City, can be done in any season. However, fall is the most beautiful in New England, but this can also bring with it lots of rain during early fall/late summer. So always check the weather before driving and be careful of slippery roads.

Summer is gorgeous of course, clear skies and easy roads make the road trip even more enjoyable.

During the winter, ice & snowfall can cause reduced visibility and slippery roads. Although, New York city is vibrant & exciting during the winter hotel prices do sky rocket!

For me the best time to make a road trip to New York city from Boston is spring, summer or late fall.

Kancamagus Highway, New England in the autumn, Photo by  (Boston to New York City Road Trip/Boston to New York City Itinerary)

Road Trip 1: Shorter.

The first version of our road trip is a shorter version which is pretty much direct, this starts at Boston, which stop overs in Bristol and New Haven, connectcuit before arriving in New York. You can choose to stop of in this cities for just a few hours, maybe have lunch, dinner or even stay the night.

  • Boston, MA
  • Bristol, CT
  • New Haven, CT
  • New York City, NY

Related Read: Best Time to Visit New England

Road Trip 2: via Rhode Island

Road trip 2 will take you via Newport, rhode island.

  • Boston, MA
  • Newport, RI
  • Martha Vineyard, MA
  • New Haven, CT
  • New York City, NY

Map of Road Trip: Boston to New York City:

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Boston to New York City: Road Trip Itinerary

This Itinerary will cover both Road Trips mentioned above then you can choose which suits you, your time and budget best!

Day 1: Boston

Boston is the vibrant capital of Massachusetts and although small it packs a big punch! If your here for just one day I suggest starting early and making the most of it!

9 a.m: Tour of the City!

Starting early, the best way to way to explore the city is by taking a door! The most popular has to be the "Freedom Trail" walking tour.

The Freedom Trail connects 15 sites of great significance in the Colonial history of the United States. The route marked with a series of painted bricks on a series of sidewalks between Boston Common to Bunker Hill Monument in Charlestown.

There are a variety of interesting stops along the way from churches and notable landmarks to signage explained interesting information and even naval warships and graveyards!

Boston Road Trip

How to book a Freedom Trail Tour?

The National Park service has a visitors center located on the first floor of Faneuil Hall. From here you can sign up for tours, and also get your hands on some free maps of the freedom trail.

Related Read: 33 BEST Places To Visit In New England

Cost of the Freedom Trail:

In general most of the sites along the Freedom trail are free, with some having a place for donations.

Due to the Freedom Trail been ran by the City of Boston’s Freedom Trail Commission which is supported in part by grants from various nonprofits and foundations including the Boston National Historical Park.

Great Boston Freedom Trail. A National Historic Trail Source:

However, in spite of this a small number of sites charge admission, these include: the Old South Meeting House, the Old State House, and the Paul Revere House.

Bus & Duck tours!

For those that would rather not walk and would prefer to see the sights on your comfy transport then book the double decker bus tour. For a unique tour book the world famous duck tour, a half bus/half boat which take you on an epic tour of Boston by land & sea!

Fun Fact: The "Duck" is a renovated World War II amphibious vehicle!

11 am: Check out the Isabella Stewart Gardner Museum

After your tour head down to the  Isabella Stewart Gardner Museum. This is a cultural gem of Boston. Located inside a 15th century venetian style palace your will discover historic sculptures, paintings, rare books and opulent antique furniture.

Contact tel: +1 617 566 1401

12 p.m: Lunch time at Newbury Street!

Newbury Street Boston Road Trip. Source:

Getting hungry? Head down the famous Newbury Street, where you will discover a pleathora of trendy restaurants, cafes and shops.  For a sweet treat, check out

Georgetown Cupcakes or for a "pick me up" coffee try out Trident Café. Afterwards take a stroll around Newbury Streets many quirky boutique shops. This is the perfect place to find a souvenir or gift for loved ones.

1 p.m:  Copley Square

Copley Square is a cultural hub, here you can find a mixture of breath taking architecture, nature and landmarks. Take a walk past the Infamous Boston Marathon Finish line  and check out Boston public library a place with astonishing decor inside.

Round the square you will also find a variety of shops & eateries.

2 p.m: Relax at the Boston Common

The Boston Common, is Bostons equivalent to central park. A place of nature spreading 20ha, the perfect tranquil escape from the energetic city surrounding.

Fun Fact: Dating from 1634, it is the oldest city park in the United States.

Insider Tip: Take a Swan Boat ride on the pond, this is a great family activity.

Swan Boat Rides Boston Common.  (Boston to New York City Road Trip/Boston to New York City Itinerary)

5 p.m: Boston Red Sox Tour

No matter what your team is, the Boston Red Sox are an iconic baseball team you have to see! Established in 1953, the fans enthusiasm is contagious! Head down to watch a match or take a tour of Fenway park.

8 p.m: Head to a Food Hall!

Head to one of Bostons most famous food halls such as Quincy Market, which houses nearly 40 gourmet food vendors. Just 10 mins walk from there is Faneuil Hall, in Bostons little Italy district.

Quincy Food Market

For more info on these great food halls check out:

Ultimate Foodie Road Trip: East Coast, inc Maps!

10pm: Stay the Night in Boston

Get some rest at one of these recommended hotels in Boston, before carrying on your road trip in the morning. You could easily spend a few more days in Boston, so feel free to extend your trip.

Day 2: Newport, Rhode Island

Starting of early in the morning take the 1hr 30 min drive (70 miles) to the quaint town of Newport in Rhode Island. The fastest way here is via I-95 S. Arrive in Newport town center

Drive into the town center and marvel at the colonial architecture, great photo opportunities. Afterwards take a walk down by Bowens Wharf and then along Thames Street where your'll find a variety of cafes, restaurants and quaint stores. Drive to Fort Adams

Fort Adams was built during the Civil War era (1799) to defend the the US coast from threats from the Atlantic. The Fort is now an historic museum.

Insider Tip:

You are free to roam around the outside of the museum but a tour is needed to go inside.

Opening times: Weekends from 10:00 AM – 3:00 PM, weekdays 12:00 PM and 2:00 PM. The tour takes about one hour and the guides are very educational!

12:00 pm: Lunch at Castle Hill Inn

Head to Castle Hill inn, nearby for some lunch. Perched on a hilltop you will find this hotel with a high end restaurant attached. Great for seafood, and freshly caught lobster or oysters.

1:00 pm: Brenton Point State Park

Afterwards take a drive along Ocean Ave to Brenton Point State Park. Here you will find a tranquil place popular with kite flyers.

2:00 pm: Check out Newports Mansions

Apart from Jay Lenos Mansion, Newport has a variety of other Mansions which are a true example of 19th Century opulence and excessive luxury.  The Mansions look like they should be housing blue blooded royals!

In fact, the preservation society owns all 11 of Newports mansions. They are open to the public for viewings & tours.

The most popular one is called "The Breakers" but "Marble House" is fantastic also. Single tickets can be purchased for each mansion and bulk discount tickets if you are visiting multiple Mansions.

Insider Tip:

Last entry is at 4:00 PM at the mansions, so if you plan on visiting a few, be sure to watch the clock.

3:00 PM: Take the Cliff Walk!

The Cliff Walk is 3.5 miles long, you don't have to trek the entire lot. But just take a stroll from Easton Beach and follow the shoreline. This will bring you to the famous Mansions.

Insider Tip:

Parking can be find at the roadside on Marine Avenue, if you wish to park up there before taking a stroll .

4:00 pm: Eastons Beach

If visiting during the summer months, check out Eastons Beach, a great place to take a beach walk or try an activity such as swimming. There is also an aquarium and for families a playground.

6:00 pm: Head for Dinner

Head for dinner at one of Newports great restaurants such as: 22 Bowen's Wine Bar & Grille, which serves Steak and fresh, local seafood. All in a classy nautical-themed dining room with waterfront views.

For a more casual venue check out: The Red Parrot Restaurant, which offers three levels of dining in a spacious 1898 building.

This is one of the most popular restaurants in Newport and has huge menu with a focus on seafood (particularly lobster) in addition to  pizza, pasta and cocktails.

Related Read: 35 Romantic Outings in New York City

10pm: Stay the night in Newport

You can chose to stay the night in Newport and visit Marthas Vineyard in the Morning or just get straight back on the road. Another option would have been to visit the city of Providence before hand.

Day 3: Marthas Vineyard, MA

Marthas Vineyard is the largest island of Massachusetts and lies just south of cape cod.  The Obamas recently purchased a Mansion here for $14.85 million from Boston Celtics co-owner Wyc it must be a nice place!

Marthas Vineyard is famed for it's quaint lighthouses, Idyllic scenery, beaches & gothic cottages in Oak Bluff. Here are the top things to do there.

  • Check out Gingerbread Houses of Oak Bluff.
  • Take a ride on the Iconic Flying Horse Carousel.
  • Greet the Island Alpacas.
  • Visit the Felix Neck Wildlife Sanctuary.
  • Check out Edgartown Harbor Lighthouse.
  • Eat at Martha's Vineyard Gourmet Café & Bakery.

Marthas Vineyard Massachusetts USA Oak Bluffs Cottages Road Trip. Source: KenWiedemann/iStock/Getty Images Plus

Why is it called Marthas Vineyard?

A smaller island further south was named "Martha's Vineyard" by the English explorer Bartholomew Gosnold, who sailed to the island in 1602. It is believed that the name stems from Gosnolds as his mother in Law was named Martha.

How to get to Marthas Vineyard:

Marthas Vineyard can only be reached by boat or air. Take the 30 minute drive from Newport to Quonset Point. From there you can catch the Vineyard fast ferry, to Marthas Vineyard.

How much does the ferry cost?

The Ferry costs $15 for adults and $8 for children 5 to 12.

How long does the journey take?

The ferry takes 1 hour 40 mins from Quonset Point to Oak Bluffs.

Where to stay at Marthas Vineyard?

Marthas Vineyard can be quite expensive to stay, so depending upon your budget either take the ferry back or check out this list of recommended accommodation. Mansion House Inn on Martha's Vineyard or the Harbor view hotel are both favourites to stay.

Day 4: New Haven, Connecticut

Take the 1hour 50 minute drive along the coast I-95 S (100 miles) to New Haven, Connecticut.

New Haven, CT is definitely one of the most underated cities in the USA and definitely in New England. The town has a great culture, history and even a thriving culinary scene!

New Haven Connecticut. Source: Getty Images.  (Boston to New York City Road Trip/Boston to New York City Itinerary)

Yale University Tour:

I'm not asking you to enroll! But it's definitely worth taking a tour of this iconic institute. The third oldest university in the U.S.A. It was established in 1701 and is a hub of great history, art and architecture.

Free Tours!

Yale offers two free tours of the university grounds. Either a self guided walking tour where you can follow an audio guide, which can be downloaded here.

Or take an 80-minute, student-led tour, which is offered twice daily on weekdays and once each afternoon on Saturdays and Sundays.

yale-university- (Boston to New York City Road Trip/Boston to New York City Itinerary)

The Student tour is pretty educating and fun. check out the ancient books such as Beinecke Rare Book and Gutenberg Bible and gain an insight into the fraternity traditions and secret societies such as Skull and Bones!

Yale has educated some of the most powerful and prominent figures in the United States. This include:

  • George W Bush
  • Meryl Streep
  • Sigourney Weaver
  • James Franco

Rope Adventure Park

Adventurers should try out the LARGEST rope adventure park in the world! This is a great place for families and adrenaline junkies it includes a pleathora of zip lines, rope birdges, and climbing walls.

Museums of New Haven

Yale University operates three major Museums:

Peabody Museum of Natural History  Which includes, the Great Hall of Dinosaurs, Egyptian antiquities and a hands-on Discovery Room. This place is great for families.

Insider Tip:

Thursday afternoons when admission is by pay-as-you-wish donation

For Art buffs, check out  Yale University Art Gallery, this museum has a series of collections from small works of art to over 200,000 objects! Just opposite check out the largest collection of British art work outside the U.K and the Yale Center for British Art.

Hungry? Take part in the Pizza wars!

In 1925, an Italian immigrant named Frank Pepe created New Haven’s signature style of pizza, with the thin-crust, coal oven–baked tomato pie topped sprinkled with grated cheese.  Since then his pizzeria is still going strong Frank Pepe Pizzeria Napoletana in New Havens, Wooster Square Italian neighborhood.

You should also try their rival Sally’s Apizza, founded in 1938,  this pizzeria was owned by the same family for nearly 80 years!

East Rock Park

Check out the epic views of New Haven from East Rock Park. You can drive right up to the summit and take in the breath taking scenery. This is especially beautiful during the fall.

Day 5: New York, New York

Hop in your car and take the coastal road down to New York City, this should take you around 2 hours (70 miles) depending upon traffic.  The coastal road I-95 S runs through Fairfield and greenwich...before taking you through the bronx and into Manhattan!

Welcome to the big apple, due to the size of New York you should really spend at least 5 days here to experience the city.

However, as this is day 5 of our road trip already other commitments meant we have just two days. So here is our 2 day Itinerary for New York!

Drive/walk over Brooklyn Bridge

Brooklyn Bridge is one of the most iconic places in New York City. Either drive straight over or take the subway to Downtown Brooklyn then take a walk over.

brooklyn-bridge.  (Boston to New York City Road Trip/Boston to New York City Itinerary)

Insider Tip:

The is the perfect place to capture some iconic New York City photos, great for instagram, facebook or just good old fashioned memories!

Bus New York Sightseeing Tour

If it's first time visiting New York City and don't fancy driving around yourself,  then try a hop on, hop off sightseeing bus. This is the best way to get a nice overview of the city, it's layout and some of the major landmarks.

Your guide will educate and hopefully entertain you on your journey around New York City. You can drive yourself but if

Tour highlights include:

  • Empire State Building
  • SOHO/ Little Italy
  • Brooklyn Bridge/ City Hall
  • Wall Street/ Charging Bull
  • High Line
  • Madison Square Garden

Ground Zero - 911 Museum

Coming the 911 Museum can be a moving and emotional experience for many, especially if they had family members or friends involved in the terrorist attack.

The Museum details the events leading up to the attack and honors the lifes lost. Budget at least one hour to this or swing by at the end of your day.

Intrepid Sea Air & Space Museum (Indoor Option)

Intrepid Sea, Air and Space Museum  is an exciting interactive venue, which is sure to keep the whole family happy. Here you can check out the USS Intrepid, fighter jets, tactical submarines with missiles attached and of course the enterprise space shuttle!

Intrepid-sea-air-museum.  (Boston to New York City Road Trip/Boston to New York City Itinerary)

For more on this check out: 15 Epic Maritime Museums: USA Navy!

Empire state Building:

Head to the top of the Empire Estate Building for the most epic view over New York City. On the 86th Floor, you will see Panoramic views of the entire city. This is a nice place to get your bearings on the cities boroughs and landmarks.

empire-state-building-view from the top!.  (Boston to New York City Road Trip/Boston to New York City Itinerary)

Insider Tip:

There is a security line, which can get quite busy so budget at least 1-2 hours for the whole thing.

Rooftop Cocktails at Pod 39 - Empire State Alternative!

Wrap up your day with some rooftop cocktails at Pod39, this terrace offers tasty tacos and breath taking views over New York city.

Day 6: New York City

Central Park

A classic location in New York City, at 843 acres central park will give you a real feel for the New Yorker culture and atmosphere, whilst being surrounded by beautiful nature.

A popular attraction is the Strawberry Fields, commemoration area where John Lennons Ashes were scattered after his fatal gunning down in New York, by a crazed Anti fan! For more on this check out: Celebrity Graves Road Trip: U.S.A


  • Bethesda Fountain and Terrace
  • Central Park Zoo
  • Central Park Carousel
  • Loeb Boathouse
  • Many more!

While it would be extremely difficult to see all the highlights of central park in just a short afternoon, make a list of a few and then give yourself enough time to see them.

There are also walking tours through Central Park.

Grand Central Terminal

Grand Central Terminal is the perfect place to capture the true essence of New York City! The Train station was constructed in 1871 and is even more busy then ever before!

grand-central-station  (Boston to New York City Road Trip/Boston to New York City Itinerary)

Times Square (free activity!)

Taking a walk through Times Square, is a great FREE activity to do in New York City. Although there are many tourists here, it's completely free and there are many activities & entertainment around.  Street Performers flock here, which are great entertainment.

Bryant Park

If your visiting New York city during the winter, head down to Bryant Park to watch the Ice Skaters it's also less touristy than Central Park. If your here in the Spring check out New York Fashion Week.

Related Read: 10 Best Cape Cod Hiking Trails

Chinatown & Little Italy - Is it worth it?

Chinatown and Little Italy are worth a visit for entertainment value, but to to be honest you will get better food in Queens (Flushing area) or Bronx (Arthur Avenue for Italian dishes!) - New Yorker Tip!

Sunnyside, Queens A great stop on the National Millennium route. Line 7. (Boston to New York City Road Trip/Boston to New York City Itinerary)

Lady Liberty Cruise (Outdoor Option)

This is a great activity during the summer months. Enjoy a educating sailing excursion around the Statue of Liberty. From the cruise you will also be able to spot other landmarks such as Ellis Island and Freedom tower.

Most of these tours offer insider stories about all the famous landmarks of New York, so you will be able to tell your friends some cool facts after finishing.

Want more epic road trips?

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Tobi Miles
Article updated:
March 28, 2024
A nomadic wordsmith savoring the world's flavors and penning stories that turn every journey into an epic.
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*Terms apply. To participate, enter your email to sign up for the newsletter . You must be 18+ and be a resident of the US. No purchase necessary. Begins January 1st  and ends February 28th, 2024. Winner announced on March 31st. For full rules and regulations, visit our Terms & Conditions page. Data  processed according to our Privacy Policy.
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