The Ultimate Long Island Day Trip from NYC: Montauk, Port Jefferson & the Best Lobster Roll on the Island

Some of the best adventures start before the sun even comes up. Living on Manhattan's Upper West Side, I've always known that the beaches, vineyards, and seaside towns of Long Island are practically in my backyard — just a couple of hours away by car. This past weekend, I finally traded the skyline for ocean air, and it turned out to be one of the best day trips I've ever taken from New York City.

Here's exactly how the day unfolded — history, food, and all.

Hour One: A Scenic Drive Through the Hamptons

Leaving the city while it was still dark out, the drive itself became part of the adventure. Cutting through Southampton and East Hampton, it's easy to see why these towns have become shorthand for the American summer. Hydrangea-lined driveways, quiet village centers, and glimpses of the Atlantic between the trees set a completely different pace than Manhattan — and the trip hadn't even reached Montauk yet.

Fun fact: The Hamptons take their name from the English town of Southampton, settled by colonists in 1640, making it one of the oldest English settlements in the state of New York.

Breakfast Stop: Carissa's Bakery

Every good road trip needs a great breakfast stop, and Carissa's Bakery delivered. The line out the door should tell you everything — this place has built a serious reputation on artisanal breads, croissants, and pastries made with simple, high-quality ingredients.

🥐 Local Favorite: The almond croissant, paired with a strong iced coffee — worth the wait, every time.

Standing at the Edge of New York: Montauk Point Lighthouse

The centerpiece of the entire trip was reaching Montauk Point Lighthouse, standing at the literal easternmost tip of New York State.

Commissioned by President George Washington in 1792 and first lit in 1796, it's the oldest lighthouse in the state of New York and the fourth-oldest active lighthouse in the entire country. For more than two centuries, it has guided ships along one of the busiest and most treacherous shipping corridors in the Northeast — the swirling meeting point of Block Island Sound and the open Atlantic.

Inside, the small museum is packed with artifacts from shipwrecks, tools from long-retired lighthouse keepers, and displays tracing the evolution of coastal navigation. But the real reward is climbing the spiral staircase to the top. From up there, the view stretches across the Atlantic Ocean, Block Island Sound, and the rugged coastline below — the exact view generations of keepers once watched for approaching storms and ships in distress.

Standing at the edge of the state, looking out at water that stretches uninterrupted toward Europe, is the kind of moment that puts a road trip into perspective.

The Bluff Lookout

A short walk from the lighthouse, the Bluff Lookout offers sweeping cliffside views of crashing waves and endless blue water. Watching the surf roll in while seabirds drifted overhead was, hands down, one of the most peaceful stretches of the entire day. Not every great travel memory happens in a museum — sometimes it's just standing still and looking at the water.

Lunch: The Clam Bar

No trip to Montauk is complete without a lobster roll, and The Clam Bar has been a roadside institution along Montauk Highway for decades.

🦞 Local Favorite: The classic cold lobster roll — generous chunks of sweet lobster meat, lightly dressed, served on a perfectly toasted bun, with a side of crispy fries. Simple, unfussy, and exactly what a beach lunch should be.

The Afternoon: Historic Port Jefferson

Rather than driving straight back into the city, the day continued in Port Jefferson — known locally as "Port Jeff."

This waterfront village dates back to the 1600s and grew into one of Long Island's busiest shipbuilding ports throughout the 19th century, when its harbor produced schooners that sailed as far as the Caribbean. Many of the original 19th-century buildings still stand today, giving the village its distinctive, almost New England–style charm.

Walking the harbor, popping into local boutiques, and watching the ferries cross the Long Island Sound made for one of the most relaxing stretches of the whole trip.

🍦 Local Favorite: A scoop of homemade waffle-cone ice cream from one of the harborfront shops, eaten on a bench watching the ferries come in — the unofficial dessert of Port Jeff.

Back Home to the Upper West Side

As the sun started to dip, it was time to point the car back west. The drive home is always a good time to reflect on how much one day can actually hold: a lighthouse older than the country's independence, a shipbuilding town with centuries of history, and two absolutely unforgettable meals — all without technically leaving New York State.

That's the beauty of living in the Upper West Side. In a matter of hours, the busy sidewalks of Manhattan can trade places with ocean breezes and lighthouse views, and you're back home the same night with a phone full of photos and a new appreciation for how much this state has to offer.

If you're planning your own trip, here's the full route: breakfast in the Hamptons → Montauk Point Lighthouse → the Bluff Lookout → lobster rolls at The Clam Bar → an afternoon in Port Jefferson → home to the Upper West Side. One day, one tank of gas, and more history than you'd expect.

Have you made the drive out to Montauk or explored Port Jefferson? What's your go-to Long Island day trip stop — and did I miss your favorite spot for lobster rolls? Drop it in the comments below! 👇