If you’ve ever dreamed about trading city noise for ocean views without hopping on a plane, this road trip is your new favorite plan.
It starts in one of New York’s busiest, most exciting boroughs and ends where the land runs out, with beach towns, food stops, and photo-worthy spots all along the way.
You’ll hit boardwalks, lighthouses, tiny roadside surprises, and more good eats than your stomach can handle.
Are you ready?
1. Brooklyn
Brooklyn is one of New York City’s five boroughs, located just across the East River from Manhattan, and it’s packed with personality, culture, and nonstop things to do.
It’s known for the Brooklyn Bridge, Coney Island’s old-school boardwalk and roller coasters, and Prospect Park, which was designed by the same guys who created Central Park.
You can wander through street art in Bushwick, grab a slice at Di Fara Pizza, catch live music at Brooklyn Bowl, or shop indie vendors at Smorgasburg, a huge weekend food market by the water.
Don’t miss the views from the DUMBO waterfront or a walk through Williamsburg, where every corner has a coffee shop, thrift store, or rooftop bar worth checking out.
2. Rockaway Beach
Next up is Rockaway Beach, Queens’ laid-back oceanfront spot that feels like a mini escape from the city without actually leaving it.
It’s the largest urban beach in the U.S., stretching over five miles, and it’s one of the only places in NYC where you can actually surf.
Grab fish tacos from Sal y Lima, rent a board if you’re feeling brave, or just chill out on the sand and watch the surfers do their thing.
There’s also a smooth bike path along the boardwalk, so bring a cruiser or rent one and ride from Beach 9th Street all the way toward Jacob Riis Park.
3. Freeport
After the beach, cruise down to Freeport, a lively waterfront town on Long Island’s South Shore that’s all about boats, seafood, and salty air.
The star here is the Nautical Mile, a fun stretch along Woodcleft Avenue filled with crab shacks, ice cream stands, live music, and dockside restaurants like Hibiscus on the Mile.
You can hop on a fishing charter, take a scenic cruise through the bays, or just wander the marina and watch the boats come in.
If you’re into wildlife, the nearby Cow Meadow Park or Norman J. Levy Park & Preserve offer peaceful walking trails and plenty of spots to spot birds and other wetland wildlife.
4. Jones Beach Island
Next on the drive is Jones Beach Island, a skinny barrier island with some of the best sandy beaches in all of New York.
Jones Beach State Park is the main draw, with over six miles of shoreline, a classic boardwalk, and spots to swim, picnic, or just lay out and do nothing.
If you’re visiting in summer, check the schedule at Northwell at Jones Beach Theater—this outdoor venue hosts big concerts right by the water.
There’s also a mini golf course, a nature center with hands-on exhibits, and biking paths that stretch for miles along the coast.
5. Robert Moses State Park
A short drive from Jones Beach Island, you’ll reach Robert Moses State Park, a quieter, more relaxed beach spot that feels like a local secret compared to busier Jones Beach.
It’s got five miles of oceanfront, wide sandy stretches, and calm vibes that are perfect for a long beach walk or a breezy picnic.
There’s a massive parking lot at Field 5 that gives you easy access to the nearby Fire Island Lighthouse—a 168-foot tower you can climb for killer views.
If you’re up for more exploring, follow the boardwalk past the lighthouse and you’ll reach nearby stretches of Fire Island, which is largely car-free, super chill, and full of cute beach towns accessible by ferry.
6. Riverhead
From the beachy calm of Robert Moses, head about 50 minutes to Riverhead, a cool little town at the start of Long Island’s North Fork that’s packed with things to do.
You can hang out with sharks and penguins at the Long Island Aquarium, ride go-karts at the Riverhead Raceway, or grab a cold cider at the nearby Riverhead Ciderhouse.
Main Street is full of quirky shops, local eats, and even a retro-looking theater called The Suffolk that hosts live shows and occasional film screenings.
And if you’re into wine, this is where the vineyard scene kicks off—places like Palmer Vineyards and Paumanok are just a short drive away.
7. The Big Duck, Flanders
Just a short drive from Riverhead, you’ll spot something totally random and totally awesome: The Big Duck in Flanders.
It’s a 20-foot-tall duck-shaped building that was built in 1931 to sell—you guessed it—ducks, and now it’s a New York roadside legend and a must-stop for a quick photo.
Inside, there’s a tiny gift shop with duck-themed everything, plus fun facts about Long Island’s duck farming history.
It’s weird, it’s wonderful, and it’s the kind of place that makes a road trip feel like an adventure.
8. Southampton
After snapping your Big Duck selfie, cruise into Southampton, one of the oldest towns in the Hamptons.
Stroll down Jobs Lane for high-end boutiques, cute cafés, and the Southampton Arts Center, which hosts rotating exhibits and outdoor concerts.
Cooper’s Beach is the go-to spot for sand and surf, with soft white sand, lifeguards, and chair rentals if you don’t feel like lugging your own.
If you’re into history, check out the Southampton History Museum or wander past the 17th-century colonial homes that still line the quiet side streets.
9. Amagansett
From Southampton, keep driving east and you’ll roll into Amagansett, a low-key beach town that’s way more chill than its flashier Hamptons neighbors.
This place is all about unpretentious charm, with spots like the Amagansett Farmers Market and live music at Stephen Talkhouse, a tiny venue where big names sometimes show up.
Indian Wells Beach is a local favorite for swimming and sunbathing, with soft sand and plenty of space to spread out.
10. Napeague
Just past Amagansett, Napeague is a super skinny stretch of land sandwiched between the Atlantic Ocean and Napeague Bay, and it’s all about peace, sand, and salty breezes.
There aren’t big crowds or fancy shops here, just wide-open beaches like nearby Atlantic Avenue Beach.
There’s also the quiet, glassy waters of Napeague Harbor, perfect for kayaking or paddleboarding.
This area is also home to the famous nearby Lobster Roll (aka “Lunch”), a classic roadside seafood joint that’s been serving buttery lobster rolls since the mid-1960s.
If you’re into nature walks, the Walking Dunes Trail has crazy cool shifting sand dunes and views of the salt marshes that feel like something out of a movie.
If you’re craving a mellow stop with beach views and zero stress, Napeague is your spot to exhale and slow it way down.
Please be aware that the Lobster Roll (aka “Lunch”) closes over the cooler months and typically reopens from April through October.
11. Montauk
End your road trip strong in Montauk, the easternmost tip of Long Island.
Start at Montauk Point State Park and check out the Montauk Lighthouse, built in 1796 and still standing tall on the cliffs with sweeping views of where the Atlantic meets Block Island Sound.
You can hike along the bluffs, watch the waves crash, or spot seals lounging on the rocks in cooler months.
Afterward, grab some food at The Montauket or head to the area around ‘The Plaza’ for more food and drink options.
Then kick back on Ditch Plains Beach and soak up the last bit of sun and scenic views before heading home.
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