Road Trip from NYC to Boston

This post may contain affiliate links so we may receive compensation if you sign up for or purchase products linked to below. As an Amazon Associate, I can earn from qualifying purchases. Read our disclosure for more information.

Feeling cooped up in your Manhattan apartment? Or perhaps you need to get away from Brooklyn’s brick stone houses. 

Whether you’re from downtown or the Bronx, Queens, or Long Island, if you’re itching to get out of the Big Apple, consider taking a road trip to New York’s sister (but more like rival) city, Boston! 

While anyone could make this drive in an afternoon, here are 9 stops along the way to help you savor your escape.

1. Van Cordtlandt Park and Museum

The road to Boston isn’t long! Making every mile count means our first stop is closer to home than one might think.

Van Cortlandt Park, located just north of the New York Botanical Gardens in the Bronx, is the third-largest park in NYC—bigger than Central Park! Don’t let the park service’s 1990s-style website fool you, the park has plenty of great activities.

Consider taking a walk around the Van Cortlandt Lake or having an early pit-stop picnic on the massive Parade Ground. You could also check out the old Van Cortlandt House Museum, an old plantation house that shows both the highs and lows of 17th-century living and culture.

Or, on the east end of the park, take a thoughtful stroll through the Woodlawn Cemetery.

Not only can you pay your respects to some of America’s most celebrated artists—from Herman Melville to Duke Ellington—it also functions as an award-winning Arboretum, with pines, spruces, elms, and firs from all over the world.

Van Cortlandt Park is the perfect warmup to get your Road Trip in motion. You can hit the road in the afternoon and arrive at our next stop before sunset!

2. Stop In Spooky Sleepy Hollow

It won’t take long to get out of New York. Why not milk your time in your favorite state! Afterall, getting out of the Big Apple is about slowing down your pace. What better way to embrace your relaxation than spending some time in the beautiful Hudson Valley!

The Hudson Valley is full of so many historic sites, it’s hard to know where to begin! Headed north, one of the first towns you’ll come across is the legendary Sleepy Hollow, where you can experience this infamous tale first hand.

This town will get you in the spooky spirit if you’re traveling in October! Not to mention you’ll witness the enchanting changing leaves of autumn.

Sleepy Hollow is home to another legend: Kykuit, the incredible Rockefeller Estate. Book a tour of the grounds and learn of the successes of one of the most well-known American Dreamers.

3. State Parks in the Hudson Valley

If you’re mesmerized by the spirit of the Hudson River, you’ll want keep heading north into the heart of the Hudson Valley.

As you travel along the river, you can’t miss New York’s collection of gorgeous State Parks. If you love a moderate hiking challenge, you could cross the Hudson into Bear Mountain State Park.

Atop a series of 3 to 7 mile hikes, you’ll be reward with unbelievable views of the Valley below.

For a more relaxing afternoon, take the family for a swim in the enormous pool at Franklin D. Roosevelt State Park. You could also tour the historic Bannerman Castle, located on an small island in the middle of the Hudson River, along the Hudsom Highlands State Park.

If you happen to drive as far north as Poughkeepsie, and stop by the Frances Lehman Loeb Art Center at Vassar College, you’ve gone too far! It’s time to head east.

4. The Capital of Conneticut

The Road to Boston carves through Conneticut. Its capital city, Hartford, is the home to many underrated adventures!

The first must-see stop is the Mark Twain House, the home to one of the most celebrated authors in American history. With its 11,500 square feet and 25 rooms, this house is a work of art in its own right. 

Not far from the Mark Twain House is the Elizabeth Park Conservancy, home to the Helen S Kaman Rose Garden, the first municipal garden in the entire United States. There are 8 other gardens to enjoy on a warm summer afternoon.

Finally, head to downtown Hardfort to check out some of its cultural hotspots. Another first in the US is the Wadsworth Atheneum Museum of Art, housing over 50,000 pieces of European and American art.

If you’re more partial to the performing arts, the Hartford Stage puts on some of the nation’s best plays and musical, for a little Broadway away from home experience!

5. Basketball, Dr Suess, and BBQ

If you’re itching to get to Massachusetts, you could jump capitals to Springfield, 30 minutes north of Hartford.

Springfield is the home of the world’s most unlikely pairing: the Basketball Hall of Fame and the Amazing World of Dr. Suess Museum. Take a tour of basketball’s greatest heroes in the morning, then walk through the Dr. Suess Memorial sculpture garden before heading into the museum.

Springfield is also offers some renowned eateries. There’s the Student Prince Cafe, serving traditional German wurst and schnitzel, accompanied by European terrace-style outdoor seating and a traditional bar inside. 

There’s also Theodore’s, a downtown favorite. This lively joint boasts “Booze, Blues, and BBQ”: your one stop for great drinks, live music, and a finger-licking rack of ribs.

6. Worcester

You’re almost there! You can almost taste the clam chowder. But before you roll into your historic destination, it’ll be worth it to make one last stop in Worcester.

Worcester has a number of great museums, from its own collections of Art to the animal-friendly Ecotarium to the quirky Sprinkler Factory

It also has a number of large parks. The local favorite is Elm Park, with its sports fields, playgrounds, and relaxing picnic areas. Alternatively, there’s Green Hill Park, which is welcoming to families with small farm zoo.

8. Destination Boston

After making this short road to Boston as long as possible, you’ve finally arrived! But you probably haven’t lost your itch for adventure. So don’t miss out on these Must-Do’s in Boston itself.

If you haven’t already, make a visit to Boston’s historic Universities. Namely: Harvard and MIT. Being one of America’s oldest institutions of education, Harvard is also one of its most eye-catching. 

Boston is full of American history. From Paul Revere’s original house to the Boston Common, you can spend entire days exploring the ins and outs of Boston’s heritage. 

So take your time, and don’t forget to grab some seafood straight from the source in Boston’s West End neighborhood.

9. The Scenic Route

Once you’ve lost your accent a bit and got your fill of Boston’s history and harbor, why not take the scenic route home. When you hit Hartford for the second time, take I-91 south toward New Haven, and make the rest of your drive along Conneticut’s southwestern coast.

In New Haven you will be tempted to compare Harvard to all things Yale, and you can stop off at the beach at Sherwood Island State Park for a reverse view of the Long Island Sound.

In the final stretch, Babcok Preserve and the Audubon Center, both located in Greenwich, offer some final wildlife respites before you return to you the shadows of the Manhattan skyline.

You’ve made it! To Boston and back, with a new list of adventures crossed off your bucket list!


FAQ Section

The Essentials Road Trip Prep Guide

Before you embark on your awesome Road Trip, you want to make sure you have the following details ironed out.

While Road Trips have a “spontaneous” feel to them, the only surprises you should be seeking are strange anecdotes from locals and picturesque moments in unexpected places. Not a full hotel or a flat tire!

How far in advance should I book my trip?

From hotel rooms to museum tickets, make sure you make your bookings at least one month ahead of time. You never know if there’s a softball tournament in town or a special exhibit on showcase the week you happen to be making your trip. Give yourself plenty of notice and call ahead. 

Plus, you might learn about some special Music Festival or Film Screening that you can now make part of your adventure!

Should I get take my car into the shop before my trip?

Absolutely! Make sure you’ve had your oil change and that there’s plenty of coolant and wiper fluid. While you’re at it, make sure your tires are freshly topped off! The last thing you want is to catch a flat 25 miles on your way out of town!

Should I pack my own snacks? 

Most definitely. You never know when a stretching of the legs might turn into a curiosity hike. You’ll want to have some granola bars, fruit, and plenty of water on hand.

There’s nothing wrong with treating yourself to delicious eateries on your journey, but some of these basic energizers can rack up in cost if you try buying them at gas stations or gift shops.

What should I wear? 

Check the weather forecast and dress accordingly. You should have a pretty good idea depending on the time of year of your trip, but you never know when a New England gust could turn into a bone-chilling breeze.

This is just another way planning ahead will help you make the best of your getaway! 


I'm the owner of Beast Auto. I live in Phoenix, Arizona. I love anything automotive related, and taking road trips all across my beautiful state.