What used to be a seasonal playground for the wealthy has transformed into a year-round lifestyle. Back in April 2010, East Hampton (which includes Montauk) had a population of around 21,400. Today, it’s grown to over 28,300. The Hamptons is made up of two main towns: Southampton and East Hampton, with Montauk at the eastern tip of East Hampton. Both are undeniably upscale, but they cater to different tastes: The Hamptons is all about not-so-quiet luxury, while Montauk is a more laidback (but still trendy) surf town.
After the pandemic, many who fled the city for the coast decided to stay put, and with them came new infrastructure. It’s no longer just ice cream parlors and linen shops—now, new healthcare, dining, and retail businesses are popping up, making this area a prime spot for year-round living.
Food
- Shark Bar (2167 Montauk Hwy, Montauk, NY): This beachside surf shack along Napeague’s sandy stretch serves up tiki classics—think lobster fried rice and crispy calamari. If the phrases “heaping portions,” “flip-flop friendly,” and “sandy, salty beer” make you smile, you’ve found your spot.
- Harvest on Fort Pond (11 S Emery St, Montauk, NY): Rub elbows with A-listers around an outdoor fire pit before your reservation at this top-rated Italian restaurant. Whether you’re a local or just visiting, Harvest on Fort Pond is the quintessential Montauk spot for summer alfresco dining.
- Rowdy Hall (177 Main St, Amagansett, NY): A French-accented pub that recently moved from East Hampton Village to Amagansett—not without a bit of drama. The beloved spot had a battle with the town’s review board over its brand image and exterior color.
- Bambi’s Cafe (33 Carl Fisher Plaza, Montauk, NY): This woman-owned cafe serves up locally sourced, 100% organic food, and locally roasted coffee. With everything made from scratch (including the nut milks), you can feel good about every dollar spent here.
Attractions
- Montauk Yacht Club (32 Star Island Rd, Montauk, NY): Following a multi-million-dollar renovation, the Montauk Yacht Club is ready to impress with new dining experiences and amenities including a revamped fitness center, three pools, plus courts for tennis, padel, volleyball, and bocce. And with the largest marina in the Hamptons, it’s the ultimate staycation for boating enthusiasts.
- LongHouse Reserve (133 Hands Creek Rd, East Hampton, NY): Created by the legendary textile designer Jack Lenor Larsen, this 16-acre sculpture garden is as much an art gallery as it is a botanical retreat.
- Montauk Lighthouse (2000 Old Montauk Hwy, Montauk, NY): Commissioned by President George Washington in 1792, the Montauk Point Lighthouse was the first lighthouse built in New York and remains the fourth-oldest working lighthouse in the country.
- Wolffer Estates Vineyard (139 Sagg Rd, Sagaponack, NY): This upscale vineyard is one of Long Island’s finest. Catering to local demand, Wölffer Estate is renowned for producing two of the top five rosés in the world… and doing so sustainably.
Nightlife
- Surf Lodge (183 Edgemere St, Montauk, NY): Whether you’re there for the nightlife or the accommodation, Surf Lodge delivers on all fronts. This boutique hotel and celebrity event space is a Montauk hotspot that is equal parts relaxed and rowdy.
- The Clubhouse (174 Daniels Hole Rd, East Hampton, NY): With two bars, live music, a dance floor, and huge TVs for game day, The Clubhouse has something for everyone. And for the extra restless, there’s also an arcade, bowling alley, and pickleball courts.
- Gurney’s Beach Club (290 Old Montauk Hwy, Montauk, NY): This Mediterranean-inspired venue has a full-service restaurant, bar, beach club, and seawater spa. It’s where high-rolling couples and partygoers sip on flowing cocktails and DJs spin tunes every summer weekend.
Neighborhood Festivals
- Southampton Arts Center’s SummerFest Gala: This benefit gala is a staple of the Hamptons social calendar. The evening begins with a cocktail reception, followed by dishes from East End restaurants and performances by Broadway stars and a quartet from The Mannes School of Music.
- Hamptons Festival of Music: A newcomer to the East End’s classical music scene, this festival brings together top musicians from North America’s leading orchestras for a series of world-class performances.
- Montauk Music Festival: A grassroots, volunteer-run celebration of Montauk’s emerging music scene. This weekend-long festival calls on over 400 artists across various genres including rock, reggae, jazz, and flamenco.
Best Beaches
- Coopers Beach (268 Meadow Ln, Southampton, NY): Powdery shores, roaring waves, and historic mansions as your backdrop—Coopers Beach is one of the best beaches in the state. Like most things in the Hamptons, be prepared for a steep price tag on parking and amenities.
- Cupsogue Beach County Park (975 Dune Rd, Westhampton Beach, NY): This 296-acre beach park at the eastern end of Fire Island is the place for lifeguard-supervised swimming and saltwater bass fishing.
- Ditch Plains Beach (18 Ditch Plains Rd, Montauk, NY): Located on the Montauk Peninsula, Ditch Plains is famous worldwide for its surfing and bodyboarding. If you’re a pro or rookie surfer or just enjoy a good windy walk, this is your spot.
Living in Long Island’s South Fork
Living in the Hamptons or Montauk means saying goodbye to daily city trips. The drive from New York City can stretch over three hours. However, if you’re without a car, the Hampton Jitney bus, Long Island Rail Road, or flights into Islip Airport (ISP) can all connect you to Manhattan, Brooklyn, Long Island, or New Jersey.
The area’s exclusivity is reflected in the cost of living. The median listing home price in Southampton is $2.7 million, while Montauk’s is $1.7 million. Summer rental prices also vary wildly—last-minute stays during peak season start around $500 per night for a standard room, while private oceanfront homes can fetch over $100,000 per month.
