There’s something bittersweet about Labor Day weekend on Long Island. Every year the fun and excitement of summer flies by so quickly that somehow Labor Day always manages to sneak up on us. It’s the final toast to summer; and there is a ton to explore. Create new memories at one of Long Island’s award-winning beaches, unwind with a glass of wine from the North Fork’s wine country, or party it up at a live music performance.
Here’s your guide to spending the long weekend on Long Island:
For Live Music and Entertainment:
Billboard x Montauk Yacht Club – DJ Oli Benz
Aug 31, 5–8 PM
Close out August at the Montauk Yacht Club with waterfront music featuring DJ Oli Benz. Expect an electric atmosphere, great drinks, and the perfect Montauk sunset over the docks.
Planting Fields – Vivaldi Celebration
Aug 30, 1–2:30 PM
Enjoy an afternoon of classical music surrounded by the lush gardens of Planting Fields. Did you know the Olmsted Brothers, John Charles Olmsted and Fredrick Law Olmsted Jr., who are famously known as designing NYC’s Central Park, also were the architects who designed Planting Fields? Explore the greenery while celebrating Italian composer Antonio Vivaldi.
Guild Hall – Silent Disco in the Garden
Aug 31, 8–11 PM
East Hampton’s Guild Hall is hosting their annual silent disco, a dance party where every guest wears glowing headphones and chooses between a few different channels of music. There will be food, drinks, and a whole lot of fun.
Sannino Vineyard – Live Music with High Street Band
Aug 31, 1–4 PM
Order a flight, have a bite, and tap your toes to familiar tunes sung by the High Street Band, playing hits from the 50s through the 2000s.
CM Performing Arts Center – Labor Day Ticket Deals
See a show! Save 25% on standard tickets to any main stage or CM Teens production using code LABORDAY25, or get 20% off family theater tickets with LABORDAYFAM. The perfect indoor, air-conditioned activity.
Hamptons International Film Festival – 17th Annual SummerDocs Series
Aug 29, 7 PM
Film lovers won’t want to miss the final installment of the Hamptons International Film Festival’s SummerDocs series at Guild Hall. Watch the screening of documentary “Middletown,” and stay around afterwards for conversations with the acclaimed filmmakers and guests, including HIFF Chief Creative Officer David Nugent, and HIFF Co-Chair, Alec Baldwin.
Instagrammable Experiences:
East End Charters – Brunch & Sunset Sails
Set sail into the weekend with a Sunday brunch cruise or opt for a romantic sunset schooner sail through East End Charters. Either way, you’re in for unforgettable views of the coastline. Gather a group and reserve your spot today!
Hampton Classic Horse Show – Final Days!
Through Aug 31
Don’t miss the final weekend of this iconic Bridgehampton event, the 50th Annual Hampton Classic Horse Show. Mingle with locals and celebrities, shop from dozens of vendors, and catch the excitement of equestrian competitions all-day long. The dress code is “country casual,” but make sure you wear comfortable walking shoes.
Tiki Boat LI – Holiday Discount!
Aug 29--Sept 1
You don't have to travel to Hawaii for tiki-bar experience. Gather a group and board the Tiki Boat LI out of Port Jefferson for a day like no other. The Tiki Boat has a full bar, can play any requested tunes, and delivers unmatched service. When booking your time slot, use code "DSLI10" for a discounted ticket.
RGNY – Dinner in the Vines, Harvest Series
Aug 28
Part of their seasonal Harvest Series, this dinner pairs fresh, local cuisine by Chef Ryan Carroll with RGNY’s award-winning wines, all enjoyed under the stars in the vineyard rows of RGNY.
Southaven County Park x Long Island Live Steamers – Miniature Train Rides
Aug 31, 10:30 AM – 3 PM
Take the kids (or your inner child) on a miniature train ride through Southaven County Park.
Coopers Beach – Sandcastle Contest
Aug 30, 12–2 PM
Head out east to Coopers Beach in Southampton, which was ranked #1 in the nation by acclaimed beach expert, Dr. Beach. Either unleash your inner artist and entire the contest, or walk along the shore and see the artists at work, sculpting the white sand into all different familiar shapes.
Belmont Park Village – Denim Is the Blueprint Event
Aug 30–31, 12–6 PM
Join a unique fashion experience at the Central Plaza in Belmont Park Village with a denim customization station and complimentary fashion sketch with qualifying purchases. Shop til you drop and buy your autumn wardrobe.
Seasonal Favorites:
Splish Splash – One Last Splash
Season Ends Sept 1
Take one final ride down the slides before the water park closes for the season.
The Shinnecock Nation – 79th Annual Shinnecock Indian Powwow
Aug 29 – Sept 1
Held in Southampton, the Shinnecock Indian Powwow is one of the biggest powwows on the East Coast, attracting thousands of visitors each year. The event celebrates the heritage of the Shinnecock Nation and broader Native American culture, complete with traditional dance, music, drums, food and crafts.
Hue Studio Fine Art Academy – Annual Summer Slime Workshop for Kids
Aug 29, 10:30 AM – 12 PM
Bring the kids for some end-of-summer slimemaking. The workshop supplies all materials and instruction needed to let kids create slime hands-on.
Restaurant Specials:
Blackstone Steakhouse & Rare650
Labor Day, Sept 1
Celebrate the holiday with a special deal at two of Long Island’s top steakhouses. Enjoy the full à la carte menu, prix fixe options, and 50% off bottles of wine over $150.
Labor Day, Sept 1
Take advantage of great holiday deals in Northport at Arlo Kitchen & Bar. Enjoy 50% off Magnum bottles of wine with the purchase of the restaurant’s signature tomahawk steak or porterhouse steak, or indulge in a $59 prix fixe dinner. The best part, the bar is offering Happy Hour specials all night long!
Labor Day, Sept 1
Make your reservation at The James in Babylon Village and expect a killer $59 prix fixe dinner menu, Wine Down specials such as half-off bottles over $150, and Happy Hour 4-6PM.
Stay Up to Date:
Keep an eye out on our Events Page and social media for more Labor Day deals that may drop throughout the week!
