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A New England Road Trip from NYC in 2024!

When you’re looking for a weekend getaway from NYC the concept of New England can seem a little far, and a little vague (at least as an expat where this whole country was very far and vague for most of our lives!) But you can see a lot and have a really fun time in even a short road trip from the NYC area!

Each fortnight (that’s every 2 weeks, for the Americans!) Micharne will share what she’s learned about some aspect of the US, from an Aussie perspective.

Where is New England?

New England is six Northeastern States; Connecticut, Rhode Island, Massachusetts, New Hampshire, Vermont and Maine. So from NYC you go North, and stick to the coast.

How Long Do I Need for a road trip to New England?

While this is always a bit of a “how long is a piece of string?” question, in a short road trip from the NYC area, say 3 to 5 days, I’d recommend sticking to the Southern 3 states; Connecticut, Rhode Island and Massachusetts. One thing you may have found about living in the US, is that there’s a good spread of possible holidays to make long weekends, but less vacation time. So to keep drive times reasonable for a shorter road trip, we’ve focused in on the states closest to NYC. Perhaps in a future article I’ll cover New Hampshire, Vermont and Maine, for which I think you’d really want a full week to do.

Why get there with a Road Trip?

With public transit options available to major New England cities and towns, you may wonder if the road trip experience is worth it. In short, there are a lot of fun sights that you can really only see by car, as local public transport options out of major cities, when they exist, are often very time consuming. Also this is a great trip for kids and dogs (except for the museums, for the pups, and maybe kiddos depending on patience levels!)


Coming up from NYC, I recommend going inland on one leg, and stopping at Danbury and/or Hartford, and following the coast on the other leg, and stopping in New Haven.

Danbury CT 

(1 hr 10 min – 2 hours from NYC, of course dependent on where you are coming from exactly!)

If you are a John Oliver fan, you may remember when his bit about Danbury Connecticut resulted in a sewer plant being named after him. His sign still stands at the Danbury sewerage treatment plant!

Hartford CT 

(50 min to 1 hr 10 min from Danbury CT)

This is where Mark Twain wrote “Adventures of Huckleberry Finn” and “The Adventures of Tom Sawyer” (although they are set in Missouri, FYI). On the same block is the former home of abolitionist and author Harriet Beecher Stowe, who wrote “Uncle Tom’s Cabin”. Both require tickets for timed tours, and especially in peak season you want to book these in advance.

New Haven CT 

(1.5 hours to 2 hours from NYC)

New Haven is home to the Ivy league school Yale, which has multiple museums, including the Yale Center for British Art. It contains the largest collection of British art outside the United Kingdom (you are in New ENGLAND after all!) New Haven is also famous for its thin-crust pizza, and for a unique local experience, make sure you try the mashed potato pizza!


Springfield MA 

(30 min – 45 min from Hartford CT)

Springfield was the home of author and illustrator Theodor Geisel aka Dr. Seuss. There is a magical sculpture garden with characters from his books, which will delight kids of all ages. Then for the actual ankle biters, there is The Amazing World of Dr. Seuss Museum.

Holyoke MA 

(20 min from Springfield MA)

This is a side of the road stop, where you can see real dinosaur footprints. The stop is literally called “Dinosaur footprints” on google maps, and is the closest I’ve ever felt to a dinosaur. You walk down a small track, to find rocks covered with prints, and not roped off or anything like in a museum.

Concord MA 

(1 hr 30 min from the Dinosaurs)

The North Bridge in Concord is where the first shots of the Revolutionary War were fired. It is surrounded by a very New England feeling park, and can be visited any time. Many great authors called Concord home, including Louisa May Alcott. You can visit her Orchard House, where she wrote her most famous book, “Little Women”. Tours of her house are again timed tickets, so book in advance.

Salem MA 

(40 min to an hour from Concord MA)

The Salem Witch Trials Memorial is a moving memorial to the 20 victims of the witch trials of 1692. You can learn more about the trials at the Salem Witch Museum. The city also celebrates all things witchy, and witches of pop culture, with a statue of Samantha from the sitcom “Bewitched” in the Essex Street Pedestrian Mall.

Boston MA 

(40 min to 1 hr 10 min from Salem MA)

Boston is of course a big city with enough things to do to fill an entire vacation if you wished. But for a stop for a couple of hours, the Freedom Trail is a 2.5 mile walking path that connects 16 historic sites, and is really the perfect way to see the historic highlights of the city. Don’t forget to pick up a Boston cream doughnut or cream pie while you’re there!

Plymouth MA 

(50 min to 1 hr 30 min from Boston MA)

In Plymouth Harbor lies the Plymouth Rock, which commemorates the site where the pilgrims on the Mayflower landed in 1620. It is housed in a grand structure on the edge of the water. Also in the harbor is a full-scale replica of the Mayflower II, or to step into a re-creation of a 1627 pilgrim village, head to the Plimoth Patuxet Museums.

Cape Cod MA 

(30 min from Plymouth to the western edge of Cape Cod)

Cape Cod is the whole hook-shaped peninsula of southeastern Massachusetts. It is filled with beautiful beaches, marshes, cute villages and seafood restaurants / shacks. The Kennedys famously spent time in Hyannis, and there is a John F Kennedy Museum in the town. At the northern tip of the peninsula is Provincetown, or P-Town to locals, a favorite vacation destination in the LGBTQI community. The sand dunes in and around Provincetown are spectacular, and at low tide, the Provincetown Causeway is a fun walk with great views (just check the tides before you head out!)

Rhode Island

Newport RI 

(2 hours 15 min to 3 hours from Provincetown RI)

Newport, among other things, is known for its mansions. There are 11 historic house museums which date from the 18th century to the Gilded Age. You can go into the mansions with individual tickets, or tour multiple homes. But a great way to see them from the outside is by The Cliff Walk along the coast. The walk is a 7 mile round trip of stunning homes and stunning ocean views, so allow 2.5 to 3 hours.

Providence RI 

(50 min to 1 hour 10 min from Newport RI)

Providence is another major city with no shortage of things to do. If you are there in the Summer or Fall, check to see if there is a WaterFire Lighting at night. In this unique art installation, a series of nearly 100 bonfires burn just above the surface of the three rivers in downtown Providence.

I hope these highlights inspire you to plan out your road trip! Feel free to drop other stops / things to do / sites to see in the comments! 

Micharne Cloughley

Micharne Cloughley

Micharne is a writer for TV and theatre. She hails from the Blue Mountains NSW, and currently lives in Jersey City NJ. Her favourite Aussie words are daggy and mate. Her favorite American words are y’all and Kansas City BBQ.View Author posts

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