Best Places to Spend Labor Day Weekend on Long Island

Labor Day weekend is the unofficial farewell to the summer season, and where better to celebrate the end of warmer weather than right here on Long Island. From chic seaside stays to acclaimed restaurants, here are the best places to spend Labor Day weekend on Long Island. 

Hampton Classic Horse Show

Image Credit: KindMedia

Held August 24-31 in Bridgehampton, the Hampton Classic Horse Show welcomes tens of thousands of attendees to watch top-tier equestrians compete in show jumping as one last bash to send off the summer. Aside from the competitive events, you can explore the Boutique Garden and shop from over 70 high-end vendors or try a wide variety of food options. The Hampton Classic celebrates its 50th anniversary

Marram Hotel Montauk

Image Credit: Marram Montauk

Sitting along the beach in Montauk is Marram, a luxurious but intimate boutique hotel with 96 unique rooms overlooking the ocean. Relax and reconnect at the beach just steps away from your room, unwind in a private poolside cabana, or watch the sunset around a cozy firepit. Marram’s unique experience offerings include oceanfront yoga and private surfing lessons. The laid-back but luxe ambiance makes Marram the perfect place to unwind on Labor Day weekend. 

Sound View Greenport

Image Credit: Sound View Greenport

Sound View Greenport lies on the North Fork, a modern, waterfront hotel with vast views of the Long Island Sound, hence the name. The hotel’s classic, beachy atmosphere is felt throughout each room. Explore the charm of the North Fork with complimentary cruiser bikes and check out live music at the Piano Bar and Low Tide Bar. Sound View’s stunning ocean views and beachy charm make a great spot to spend Labor Day weekend on Long Island.

RGNY Winery

Also on the North Fork is RGNY Winery in Riverhead, a sprawling vineyard founded by the Rivero González family, combining Mexican heritage with the art of winemaking. Tour acres of grapevines then test your inner sommelier with various wine flights and blind tastings overlooking the vineyard or sitting outside. If you stop by on Sunday, try their brunch a la Mexicana with a side of live music and wine pairings. RGNY Winery is the perfect spot to celebrate Labor Day weekend on Long Island with a large group of family or friends.  

Duryea’s Orient Point

Image Credit: Duryea’s

Known for its viral $97 Lobster Cobb Salad, Duryea’s, located in Orient Point and Montauk, is a chic seaside spot for some of the best seafood on Long Island. Duryea’s Orient Point is only open for the summer months and includes a trendy, laid-back beach club perfect for lounging with drinks and trying a selection from the raw bar. Choose from three different outdoor seating areas depending on the size of your group. 

Gurney’s Beach Club Montauk

Image Credit: Gurney’s Resorts

Offering over 2000 feet of private beach in Montauk, Gurney’s Beach Club is the place to drink and dine by the ocean and celebrate Labor Day weekend on Long Island. You can rent daybeds or private cabanas along the beach and drink at the walk-up bar. Shop the exclusive Dolce & Gabbana pop-up and check out the matching decor of the beach club adorned with the fashion house’s signature print. See the Sound Waves summer music series at the beach club or firepit for live music by various DJs. 

Si Si’s at EHP Resort

Try an assortment of Mediterranean cuisine at Sì Sì (“yes yes” in Italian and Spanish) in East Hampton, part of the EHP Resort & Marina. Overlooking the Three Mile Harbor, this spot offers a wide array of raw bar dishes along with tasty pastas and large dishes like spicy paella. Sì Sì’s is the perfect high-end spot with an exclusive ambiance to end Labor Day weekend on a high note.    

The Baker House 1650

Image Credit: The Baker House 1650

For the most luxurious Labor Day weekend on Long Island, stay at The Baker House 1650, a lush and private bed and breakfast in East Hampton. 17th century architecture gives a charming, historic feel to the inn, with just under 20 unique rooms. Wake up to breakfast made with organic local produce and unwind in the Baker Spa. Try an exclusive sunset cocktail hour or Sunday afternoon tea. 

Crow’s Nest Montauk

Image Credit: Crow’s Nest

Crow’s Nest lies at one of the farthest points of Montauk, serving American-Mediterranean eats. This restaurant has a rustic and romantic feel filled with wood details and a perfect sunset view of Lake Montauk. Try locally sourced fish and vegetable filled dishes, along with house-made pastas. Crow’s Nest’s beachy charm makes for the perfect dinner spot for Labor Day weekend on Long Island.