Road Trip

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New York to Cape Cod Road Trip Itinerary: Weekend Escape!

Plan your ultimate weekend escape with our New York to Cape Cod road trip itinerary. Explore quaint towns, culinary delights, and serene landscapes. Perfect for travelers.

Tobi Miles
July 1, 2022
New York to Cape Cod Road Trip Itinerary: Weekend Escape!

New York is a vibrant city, with great culture, landmarks and something to excite everyone! Its also a great starting point from many Epic US Road Trips!

As you drive out of New York City north east, you will pass such landmarks as the Empire State building and Manhattans east village known for its rebellious vibe.

As you head on this epic road trip to Cape Cod you will pass many quiant towns & states from New Haven (which has a thriving culinary scene) to Mystic, Newport and of course Marthas Vineyard.

When you arrive at Cape Cod, Massachusetts you will find a real contrast to the fast paced urban jungle of New York City. In Cape Cod you will discover a laid back vibe with quaint villages, picturesque lighthouses and that fresh Atlantic air!

So start your engines, pack your travel essentials and get ready for a wild ride!

cape cod national seashore. Source; Getty

How long is the drive Cape Cod from New York?

If you drive directly between New York City and Cape Cod you would cover approximately 252 miles (405km). This will cover a total driving time of 4.5 hours.

You can do this in a day, but stopping for at least a  night in New Haven, Newport or Marthas Vineyard is definitely recommended.

Related Read: Best Time to Visit Cape Cod

Interactive Map (New York to Cape Cod Road Trip)

User guide: Use the +/- buttons to zoom in and out of the attractions.

Top Tip: Many visitors choose to share the post on Facebook to inspire friends and help plan their road trip.

Hit the link below to share!

Road Trip Itinerary (New York to Cape Cod):

  1. New York City
  2. East Village, Manhattan NYC
  3. Lunch in Queens, NYC - Optional
  4. Stay at Delmar Spa hotel on the way back!
  5. Elm Street Diner , Stamford, CT - Ideal for breakfast on the way back.
  6. New Haven, CT
  7. Mystic, CT
  8. Newport, RI
  9. Benefit Street, (Providence) RI - Optional
  10. Marthas Vineyard
  11. Cape Cod
  12. Nantucket - Optional Day Trip

Related Read: 10 Best Cape Cod Hiking Trails

Road Trip Highlights:
East Village - Manhattan, NYC

You will drive through Manhattans vibrant east Village so its definitely worth having a look around!

The area has been know for its anti-establishment & rebellious vibe ever ever since the punk culture in the 1970s.

There you will find dive bars, Graffitied walls and the iconic St Marks Place.

Grab a snack at the 24 hour Ukrainian diner Veselka

east village manhattan

Insider Tip:

Grab a road trip read at Strand Books, established in 1927 it boasts over 18 miles (29km) of books!

Grab lunch in Queens

Grab some lunch at  Casa Enrique, New York City's only Mexican Restaurant with a Michelin star!

Located in Long Island City Queens, be sure to try its steak tacos made with thick corn tortillas. There is also its chicken enchiladas in Salsa Verde which are incredible!

Insider Tip:

Order both dishes with  Mole de Piaxtla and chile relleno.

Check in to the Delamar Greenwich Harbor

Delmar Greenwich Harbor in Greenwich, Connecticut was rated by Town & Tourist as one of the greatest Hotels in New England!

We visited here on the way back to New York City, as its the perfect place to relax in the hotels deep tubs with Bvlgari bath products.

Delamar Greenwich Harbor

Insider Tip:

Arrive here on the weekend to enjoy complimentary seasonal harbor cruises!

Related Read: 34 Best Romantic Getaways In Massachusetts

Elm Street Diner, Stamford, CT

Elm Street Diner in Stamford, Connecticut is the ideal place to grab some breakfast after a night at Delmar Greenwich Harbor.

This family owned restaurant is one of the best in Stamford, CT.

Insider Tip:

Be sure to try the mouth watering peanut butter pancakes, the Breakfast quesadillas and of course the coffee.

New Haven, Connecticut

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

Top 5 Things to do?

1. Yale University - FREE TOURS!

Take a Free tour of the historic campus, Yale has educated some of the most powerful and prominent figures in the United States. These include:

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


2. Visit the 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.

3. Rope Adventure Park

With the family? Have some Adventurers should at the LARGEST rope adventure park in the world! This is a great place for kids and adrenaline junkies it includes a plethora of zip lines, rope birdges, and climbing walls.

4. 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.

New Haven Connecticut. Source: Getty Images

5. 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!

Newport, Rhode Island

Hop on to Rhode Island Route 138 and drive over the Bridge to the island retreat of Jamestown and then into Newport.

Newport is a scenic seaside city in Rhode Island. It is famous for its historic mansions, shopping, and beautiful scenery.

Newport is also know for the Newport Folk Festival and the Newport Jazz Festival, in addition to and many other quirky Festivals and Fairs.

Related Read: 20 Top Treehouse Rentals in Massachusetts

Benefit Street, Providence - Optional

This is an option on the way back as its a slight detour...but definitely worth it if your a history buff! Benefit Street is the most famous street in Rhode Island!

Founded back in 1636, Providence is one of the most historic cities in the USA and benefit street is the one mile of history to prove it!

This is the perfect place to park up and take a stroll past the historic Victorian homes and federal mansions such as  John Brown House,. Other National Historic Landmarks include Governor Stephen Hopkins House.


Marthas Vineyard

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 Grousbeck….so 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

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.

Cape Cod

You've finally made it to Cape Cod! From Cape Cods beautiful beaches to its National Seashore & quaint beach town, Chatham there is something for everyone.

Best Things to Do in Cape Cod?

1. Relax on Cape Cods Beaches

Cape Cod is a laid back place and its beaches are the ideal spot to relax.

Insider Tip:

Cape cod has a bay side and an ocean side which both offer very different sea vibes. The water on the bay side is warmer and calmer, but you’ll have to be aware of the tides!

However, on the ocean side, expect colder temps and more waves, but the water up close.

2. Visit Cape Cods Lighthouses

Cape Cod has a number of lighthouses suitable for visiting.

There is Nauset Light erected in 1923 & stands 48 feet high.  Tours of the tower and adjacent oil house are available in summer from the Nauset Light Preservation Society which operates, maintains and interprets the site.

Highland lighthouse is another popular lighthouse to visit erected in 1857 it is the tallest and oldest lighthouse in Cape Cod!

cape cod-Highland_Lighthouse. source: wiki commons

The area is open year-round, while the light is open to the public from May until late October, with guided tours available.

Another popular lighthouse is the Race Point Light built in 1816 and 45 foot tall.

The lighthouse is reached by hiking about 45 minutes over sand, the views from the top are so worth it!

Insider Tip:

With a National Park Service Oversand Permit, a four-wheel-drive vehicle can be used.

Being New England, there are so many other lighthouses to mention, to find out more check out: Ultimate Maine Lighthouse Road Trip

3. Be awestruck by the Pilgrims Monument

At the tip of Cape Cod is Provincetown known for its vibrant art and music scene. In 1620, the Pilgrims landed here in the Mayflower.

To commemorate this first landfall in 1620 the Pilgrim Monument was built in 1907.

It stands 252-foot-7 ¹⁄₂-inch-tall and is the tallest all-granite structure in the United States. It is part of the Provincetown Historic District.

With many beaches, miles of hiking trials and cycling paths, kayaking, and of course boat excursions, Provincetown is a fun and popular resort.

4. Go Whale Watching at Cape Cod

Whale watching is classic must do experience at Cape Cod! Take a boat trip from MacMillan Wharf in Provincetown for whale watching toursto the Stellwagen Bank Marine Sanctuary, from mid-April through October.

humpback-whale-cape cod-whale-watching

With trained naturalists are on board the tour, they offer intriguing facts and tips on the different types of whales from humpback to finback.

Similar whale watching cruises also leave from Hyannis and Barnstable harbors.

Prefer cute seals?

For seal watching take a cruise from the picturesque Chatham. From Harwich Port, board a high-speed catamaran for a narrated seal cruise around the island of Monomoy.

There are also narrated tours from Orleans which are perfect for families as they offer stories of Pilgrims, pirates, and shipwrecks.

5. Nantucket

Founded by colonists in 1659, Nantucket is 15-mile-long island 30 miles south of Cape Cod.

Nantucket was the center of the world's whaling industry, with more than 125 whaling ships, as stated in the book Moby Dick!

These days the island is the perfect place for a day trip! Popular with tourists there are many beaches, historic landmarks and even Sea Captains Mansions!

Nantucket lighthouse

Other popular attractions include, The Nantucket Life Saving Museum which houses a collection of marine artefacts, and Hinchman House Natural History Museum which focuses on Nantucket's flowers & wildlife with bird, wildflower, and marine ecology walks.

Best time to visit?

Visit in April to see the roadsides are bright with daffodils, which local residents have been planting for many decades and celebrate the bloom with a colorful festival!

Insider Tip

Don't bother bringing your car here, as Hotels will meet you at the ferry or you can take a bicycle/walk to the attractions.

Best Tours in Cape Cod?

If you would prefer to have all the best places organised for you to save you any stress, check out the list of my favourite tours in Cape Cod

From day trips, private tours to kayak explorer adventures, HERE

Where to Stay in Cape Cod?

For a full list of my recommended places to stay in Cape Cod, Follow this link HERE

Essential Road Trip Tips:

Make sure you are equip with some great Photography Gear!

How to get the best car rental Deals?

Check out: Ultimate Car Rental Travel Hacks!

For RV Rentals we always use: RV Share

Bring your RV to Tiden Park.

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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