There’s nothing like a road trip from New York City to Cape Cod.
You’ll cruise past historic towns, stunning beaches, and spots so pretty they look straight out of a postcard.
Along the way, you’ll find everything from legendary pizza to gorgeous mansions, hidden boardwalks to tall lighthouses, plus plenty of spots to stretch your legs.
Whether you’re into history, food, or just chasing the best ocean sunsets, this route has it all—so get ready for a seriously fun ride!
1. NYC
New York City is a busy, exciting place where skyscrapers seem to touch the sky, yellow taxis zoom past, and bright lights make Times Square shine day and night.
It’s the perfect place to start our road trip so grab a coffee and let’s hit the road.
2. Greenwich, CT
Just 35 miles from NYC, Greenwich feels like a total change of pace with its charming downtown, scenic waterfront, and fancy mansions.
This town sits right on the Long Island Sound and is known for its yacht clubs, high-end shopping on Greenwich Avenue, and the gorgeous trails at Greenwich Point Park.
It’s a place where you can grab a snack from a cozy café, browse designer boutiques, and then unwind by the water—all while feeling like you’re in a movie.
3. New Haven, CT
About an hour up the coast, New Haven serves up history, culture, and its iconic New Haven-style “apizza” (yes, it’s different and a must-try).
Home to Yale University, this city has that classic Ivy League feel, with grand old buildings, museums, and a student-fueled energy that keeps things lively.
Whether you’re savoring a white clam pie at Frank Pepe’s, exploring the Yale Peabody Museum, or catching live music, New Haven is full of surprises.
4. Gillette Castle State Park, CT
Heading deeper into Connecticut, Gillette Castle State Park feels straight out of a mystery novel—no surprise since Sherlock Holmes actor William Gillette built it.
Overlooking the Connecticut River, this medieval-looking castle features fancy doors, handcrafted woodwork, and hiking trails with stunning river views.
Whether you’re admiring the castle’s odd architecture or picnicking along the scenic cliffs, this stop blends history, nature, and just the right amount of weird.
5. Mystic, CT
Cruising toward the Connecticut coast, Mystic is full of that classic New England charm, as well as a nautical feel that will make you dream of life at sea.
As a former shipbuilding town, Mystic now draws visitors to the Mystic Seaport Museum, where you can step aboard some of the historic vessels.
You can also check out the Mystic Aquarium which is home to beluga whales, sea lions, and incredible marine exhibits.
And if the name sounds familiar, you’ve probably heard of Mystic Pizza—yes, the actual pizzeria that inspired the ’80s movie is right here, and you should grab a slice.
6. Watch Hill, RI
Crossing into Rhode Island, Watch Hill is a dreamy little coastal village with golden beaches, grand old hotels, and old-school glamour.
Here, you’ll find the Ocean House, a picture-perfect, yellow Victorian-style hotel, and the Flying Horse Carousel, one of the oldest still-running carousels in the U.S.
Whether you’re strolling past seaside mansions or hunting for sand dollars on Napatree Point, Watch Hill is all about slow, sun-soaked, New England charm.
7. Newport, RI
A little farther up the coast, Newport cranks the seaside luxury up a notch with its Gilded Age mansions, world-class sailing scene, and endless ocean views.
The famous Cliff Walk lets you stroll along the rocky shoreline and peek into legendary estates like The Breakers, once home to the Vanderbilt family.
At the same time, Newport Harbor is also full of classic sailboats and luxury yachts.
Throw in fresh lobster rolls, a historic downtown, and the energy of the annual Newport Jazz Festival, and you’ve got a city that feels effortlessly fun to explore.
8. Plymouth, MA
In Massachusetts, Plymouth brings history to life as the Pilgrims’ 1620 landing site, complete with a view of Plymouth Rock (which may be smaller than you imagined).
You can also visit the Plimoth Patuxet Museums and see a 17th-century village, chat with Pilgrim reenactors, and learn about the Wampanoag people’s rich history.
(Please note that Plimoth Patuxet Museums closes over the winter and reopens in March.)
Plymouth also has beautiful beaches, fresh seafood shacks dishing out clam chowder and lobster rolls, and boat tours where you can spot whales off the coast.
9. Gray’s Beach, MA
Just off the beaten path in Yarmouth, Gray’s Beach is a quiet little gem with salt marshes and a long boardwalk that offers some of the best sunset views on Cape Cod.
At low tide, you can walk out onto the sandbars and watch tiny crabs scurry around!
During high tide, the calm, shallow waters are great for swimming or floating, but be careful—rip currents may appear.
It’s the kind of place where you bring a picnic, kick back on the boardwalk, and let the sound of the waves and the salty breeze do all the heavy lifting.
10. Chatham, MA
Further down the Cape, Chatham is a picture-perfect New England town with shingled cottages, hydrangea-lined streets, and a postcard-worthy lighthouse.
The iconic Chatham Lighthouse guards the shore, while the town’s Main Street is packed with shops, homemade ice cream stands, and top-notch clam chowder.
If you’re into wildlife, Chatham is famous for its resident seals— so take a boat tour if you want to see them lounging on sandbars like they own the place.
11. Eastham, MA
As you head closer to the outer Cape, Eastham is where Cape Cod’s wild side starts to shine, with sprawling beaches, windswept dunes, and unbelievable sunsets.
Home to the Cape Cod National Seashore, this town invites you to visit Nauset Light, walk the golden sands of Coast Guard Beach, or bike the scenic Cape Cod Rail Trail.
Whether you’re catching waves or just breathing in the fresh ocean air, Eastham is all about adventure, nature, and soaking up the raw beauty of the Cape.
12. Provincetown, MA
Right at the tip of Cape Cod, Provincetown is where history, art, and pure, unapologetic fun come together in one colorful seaside town.
This is the spot where the Pilgrims actually landed first in 1620 (sorry, Plymouth), but today, it shines for different reasons.
From its thriving LGBTQ+ scene and art galleries to Commercial Street’s quirky shops and seafood joints, it’s a place full of energy and personality.
Whether you’re taking in harbor views from the Pilgrim Monument, spotting whales on a boat tour, or hitting a drag show, P-Town is all about joy and freedom.
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