This Village at the East End of Long Island Is What Autumn Dreams Are Made Of
Picture this: The brisk autumn breeze carries the salty scent of the Atlantic Ocean as you wander through a charming village that time seems to have forgotten. Welcome to Montauk, New York, the jewel of Long Island’s East End and your perfect fall getaway destination from California.
Tucked away at the easternmost tip of Long Island, Montauk is a seaside escape that effortlessly combines the beauty of nature with a dash of the opulence of the Hamptons. Known as “The End,” this small fishing village is where rugged coastline meets upscale relaxation—where every sunset over the Montauk Lighthouse feels like a masterpiece painted just for you.
As the summer crowds dissipate, Montauk takes on a different persona in the fall. The vibe shifts to a slower, more serene pace, making it the perfect time to explore this little town. So, grab your coziest sweaters and forget about the warm California temperatures for a few days; take a trip to the East Coast to enjoy one of the best autumnal destinations.
Before You Go: Book a Cheap Flight to New York City
Montauk is in New York after all, which means it’s time to hop on a flight across the country. Luckily, airlines offer steep discounts on tickets after summer and before the holiday season, so fall is the perfect time to take that last-minute trip you’ve been dreaming about. Plus, the flights from Orange County and LA are direct, so it’s as easy as can be.
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Once You Get There: Rent a Turo Car
The easiest way to get to the Hamptons is by car, and the cheapest (and best!) car rental service in New York is Turo. To book a ride with Turo, simply sign up for an account, search for available cars in New York, select the car you want and book it! It’s super convenient and before you know it, you’ll be cruising out of the city and into Long Island. However, if you prefer not to drive, you can hop on the Long Island Railroad or snag a seat on the Hampton Jitney bus.
DAY 1
Arrive
Once you’ve made it from the city to the Hamptons, check into The Montauk Beach House. This historic boutique hotel is situated in the heart of downtown Montauk and is one block away from the beach. It’s also just a short stroll away from Montauk’s shops, restaurants, bars and cafes. It has a laid-back feel that Californians will love as well as a sleek, retro vibe that gives it an edge. Enjoy fires by the pool at night as well as live entertainment on the weekends.
Eat
You’re on the East Coast, which means it’s time for (quite a few) lobster rolls. Head down the road to The Lobster Roll to nosh on one of the best lobster rolls on Long Island. Although there might be a bit of a wait for a table, trust us when we tell you it’s completely worth it. If you haven’t worked up an appetite for a buttery lobster roll yet, you can enjoy a huge seafood-focused menu that includes fan favorites like Paul’s Famous Seafood Chili—a spicy blend of shrimp, lobster, scallops, and beans topped with melted cheddar cheese, sour cream, and scallions—homemade clam chowder, grilled crab cake sandwiches and so much more.
Explore
Once you’re fueled up, head to the iconic Montauk Point Lighthouse. Located on the easternmost tip of Long Island, this stunning landmark is not hard to miss. Built in 1796, it’s one of the oldest lighthouses in the United States. If you’re feeling adventurous, you can climb 137 iron steps to the lantern room for breathtaking panoramic views of the Atlantic Ocean, Montauk Point State Park and the surrounding coastline. With its scenic views and memorable sunsets, this is something you won’t want to miss.
Do
No matter what time of day it is, it’s always a good time to go to The Montauket. This waterfront restaurant and bar, which has been around since the late 1920s, has some of the best views in Montauk. Perched atop a bluff, it offers picture-perfect snapshots of Fort Pond Bay and Montauk Harbor Inlet—not to mention, some incredible sunsets. It’s a beloved local hangout spot thanks to its rustic charm, delicious seafood dishes (get the fried soft shell crab sandwich) and strong drinks. Plus, you can catch local bands, singers and performers most nights of the week on the patio.
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Enjoy
Craving more fish for dinner? We don’t blame you—you are a Californian after all. Along the Montauk highway, you’ll find one of the best restaurants on the East Coast: Clam Bar. This local hotspot is home to mouthwatering dishes that don’t skimp on the fish. Here, you’ll find lobster rolls that are practically bursting at the seams with fresh, succulent lobster that’s sure to melt in your mouth. (We told you you’d be eating a lot of lobster rolls.) Along with delicious lobster entrees, including a lobster BLT that just might make you forget about California altogether, you can find a sushi hot dog—a fried sushi roll that’s topped with marinated salmon tartar, spicy mayo, sweet soy and wasabi sesame seeds—a seared tuna sandwich, hamburgers, fish and chips and more. If you want a local Montauk spot that will knock your socks off, this is a must.
DAY 2
Arrive
Okay, since you are in the Hamptons, which is one of the most famous and luxurious spots in the US, you might as well vacation as many East Coast socialites do. Since the first day was all about enjoying the small-town feel of Montauk, today is the day to embrace the extravagance of the Hamptons. To do so, check into Gurney’s Montauk Resort & Seawater Spa. Gurney’s Montauk is a luxurious beachfront resort that perfectly encapsulates what draws people to the Hamptons. The resort has elegant accommodations, ranging from guest rooms to spacious suites and cottages that have panoramic views of the ocean. It’s renowned for its world-class amenities, including a private beach with beachside service, a huge seawater pool, a rejuvenating spa that includes impeccable treatments and a great selection of dining experiences. With its upscale ambiance and breathtaking surroundings, Gurney’s is the epitome of what it means to stay in the Hamptons in style.
Eat
After you’ve taken a beach walk or soaked up the sun on your hotel room’s private patio, head to Inlet Seafood for lunch. Located in a shipyard, this sushi spot is the best in the business. It serves fresh rolls, sashimi, nori and more, as well as salads, sandwiches and fried seafood. If you’re renting a boat, we suggest docking here for lunch since there’s plenty of room to tie up. Prefer to eat on the beach? Just take your rolls to go!
Explore
Gurney’s is known for its next-level spa, so once you’re done with lunch, head back to the hotel to enjoy some downtime. The Seawater Spa offers a range of luxurious treatments that include couples massages, healing facials and more. There’s also a bathhouse where guests can bask in warm, cold and saltwater pools. Plus, there’s a state-of-the-art gym that also hosts fitness classes each day.
Do
After relaxing at the spa, head to the Wölffer Estate Vineyard. This picturesque winery is known for its exceptional wines (you must try the Summer in a Bottle rosé) amidst a stunning vineyard setting. The vineyard specializes in producing premium wines, with a focus on classic Bordeaux varieties like merlot, chardonnay and cabernet Franc. Guests can enjoy wine tastings, tours and culinary experiences along with live music and other entertainment during the year. The bottom line: It’s a must-visit destination for wine enthusiasts and those seeking a taste of Long Island’s wine country. It might even make you ask, “Napa, who?”
Enjoy
Ready for dinner? Head to Gurney’s famed restaurant, Scarpetta Beach. This restaurant is celebrated for its modern Italian cuisine, featuring fresh seafood, housemade pasta and delectable seasonal dishes that showcase the best flavors of the region. It has a relaxed yet sophisticated ambiance, making it an ideal spot for romantic dinners, special occasions or simply enjoying a taste of Italian-inspired cuisine by the sea. With its chic setting, exceptional service and even some notable celebrity sightings, Scarpetta Beach is the one and only when it comes to indulging in the Hamptons dining scene.
DAY 3
Arrive
Time to head down Long Island and hit another hotel favorite: Baron’s Cove. If you’re looking for that quintessential East Coast vibe, this is the place. Baron’s Cove, nestled in the heart of Sag Harbor, is the coastal retreat California natives will love. First and foremost, it boasts a prime waterfront location that has stunning views of the town’s picturesque harbor. On top of that, guests can enjoy the beauty of the water while also having easy access to the village’s quaint shops, restaurants and cultural attractions. As for the best part? Both the hotel and restaurant make it feel as though you’re staying in a charming East Coast home.
Eat
Baron’s Cove features an acclaimed restaurant, The Restaurant at Baron’s Cove, which is a must-visit no matter where you’re staying. The restaurant’s ambiance is a harmonious blend of classic Hamptons elegance and nautical charm, creating a warm and inviting atmosphere. Savor a delectable menu that showcases fresh, locally sourced ingredients, with an emphasis on seafood and seasonal dishes prepared to perfection. Whether you choose to dine indoors with its cozy fireplace or on the outdoor terrace overlooking the serene harbor, The Restaurant at Baron’s Cove provides a scenic backdrop to enjoy excellent cuisine.
Explore
Learn about the history of the Hamptons at the Sag Harbor Whaling & Historical Museum. Housed in a historic Greek Revival mansion dating back to the 1840s, this museum offers a glimpse into the village’s whaling past and its role as a bustling port during the 19th century. Inside, guests can explore a diverse collection of artifacts, including harpoons, scrimshaw art, ship models and historical photographs, which all shed light on the area’s whaling heritage. The museum also showcases exhibits highlighting Sag Harbor’s broader history, from its Native American roots to its growth as a thriving maritime community. Trust us, you’ll learn a ton.
Do
Your time taking a peek at history isn’t over! Head to the Sag Harbor Cinema to experience a bit more. This landmark has been an integral part of the community for decades, showcasing a diverse range of independent and classic films. The cinema’s charming and artfully designed interior provides an intimate and cozy setting for film screenings, no matter the time of year.
Enjoy
After you’ve watched the latest flick, head to Calissa for dinner. This stylish and upscale restaurant specializes in Mediterranean cuisine, with a focus on dishes inspired by the coastal flavors of Greece. The menu features a wonderful selection of seafood, fresh vegetables and grilled meats—all prepared with a Mediterranean twist. Here, you’ll notice a lively atmosphere that attracts people who want to have a good time and nosh on even better food.
Head Home
After a lavish weekend in the Hamptons, it’s time to head out. Enjoy your last drive along Long Island before making your way back home. No matter which coast you’re from, the Hamptons is the perfect escape for any time of year.
Lauren Harano is a bicoastal editor covering travel, beauty, and lifestyle topics. Her work can be found in Cosmopolitan, Glamour, Harper's Bazaar, InStyle, Esquire, Teen Vogue, and Hotels Above Par, among other publications. When she's not writing, she can be found trying new skincare products or planning her next vacation.
