Your Complete Labor Day Weekend Guide on Long Island: Where to Eat, Play & Celebrate; Best Events, From Vineyards to the Shore

BABYLON, NY – As the sun begins to dip on summer, Long Island rolls out a full weekend of unforgettable Labor Day festivities – perfect for make‑the‑most‑of‑it celebrations. Whether you’re craving live music, cultural experiences, food‑fest fun, or beach‑side dancing, this three‑day stretch (Friday 8/29 through Sunday 8/31) offers something for everyone, from families looking to soak up the last bit of sunshine to friends gathering for one last big bash before fall.

Expect cultural traditions, high‑energy dance parties, historic powwows, and fireworks – all complementing your favorite casual escapes like mini‑golf, amusement parks, and local eats. Ready your calendars, pack those weekend bags, and get set for a jam‑packed Labor Day send‑off that delivers on the final toast to summer on Long Island.

All Labor Day Weekend Events: August 29–31, 2025

Cultural & Festivals

• 79th Annual Shinnecock Indian Powwow, Southampton – A vibrant celebration of Native American culture featuring dancing, drumming, and traditional arts. Considered one of the top‑five powwows of the year.
• Long Island Foodie Fest, Deer Park (Sun, Aug 31) – A tasty outdoor gathering with local vendors serving up the best Long Island eats, from noon to 7 PM.

Music & Dance

• Concert & Fireworks at Masone Beach, Island Park (Sat, Aug 30) – Dancefloor NY rocks the stage starting at 7:30 PM, capped off by a sky full of fireworks.
• East End Underground Live Series: REEB!, Wainscott (Fri, Aug 29, 7:30–9:30 PM) – A concert presented by LTV Studios showcasing “The Big Easy of the East End.”
• Labor Day Weekend Party with Vinyl Revival, Ronkonkoma (Sun, Aug 31) – A retro‑themed live music night at Beach Club Estate.
• Flynn’s Fire Island Beach Parties, Fire Island:
  • VAVO Holiday Dance Party (Sat, Aug 30, 12–8 PM)
  • Super Sunday Funday (Sun, Aug 31, 11 AM–8 PM)
  • Labor Day Monday with Brandi Cyrus (Mon, Sep 1, but good to know for wrap‑up plans)

Family & Fun

• Long Island Ducks Baseball Game, Central Islip (Fri, Aug 29) – Catch an evening of baseball excitement at Fairfield Properties Ballpark.
• Glow‑in‑the‑Dark Skate Night, Seaford (Fri, Aug 29, 7–9 PM) – A neon-lit roller‑skating extravaganza at United Skates of America.

Water & Amusement Parks

• Splish Splash Water Park, Calverton (Aug 29–Sep 1) – A full weekend of slides, wave pools, and family thrills at Long Island’s go‑to water destination.
• Adventureland Amusement Park, East Farmingdale – Open all summer, offering a mix of thrilling rides, kiddie attractions, and nostalgic fun.

Food & Drink Specials

• 2-for-1 Margaritas at Besito Mexican (West Islip, Roslyn, Huntington) – Available Sunday (Aug 31) and Monday (Sep 1), 12 PM–3 PM.
• Kids Eat Free at Applebee’s Patchogue – A family‑friendly meal deal all weekend long.

Summary Table

Additional Local Picks: Scenic Vineyard Escapes, Farmers Markets, Montauk

• Harbes Farms (Jamesport & Southold)
  Kick off your Labor Day weekend at Harbes Orchard & Farms – starting Saturday, August 30, you’re invited to the Annual Honeycrisp Apple Festival featuring apple picking, corn mazes, hayrides, live music, Harbes wines, and more. Plus, on Friday, August 29, enjoy the season’s final Fun Friday, featuring pig races and musical hayrides with discounted admission all day
• Macari Vineyards (Mattituck, North Fork)
  Perched on a sprawling farmstead, Macari Vineyards offers guided tasting experiences in their charming tasting room or private suite – an ideal stop for wine lovers seeking elegance and scenic views. Appointments are required.
• RGNY Winery (Riverhead, North Fork)
  For Sunday (August 31), consider RGNY Winery in Riverhead. Enjoy vineyard tours, wine flights, and even a brunch à la Mexicana paired with live music – an elevated way to toast the end of summer.

Local Flavors at Farmers Markets

• Farmingdale Farmers Market (Village Green)
  On Sunday, stop by the Farmingdale Farmers Market (10 AM–2 PM) for fresh produce and artisan goodies—perfect to stock up on local flavor before the weekend winds down.
• Other Local Markets (News 12 Feature)
  Explore the comprehensive guide to farmers markets across Long Island—options span roadside stands, growers’ markets, and seasonal stalls across both Suffolk and Nassau counties.

Montauk Highlights & Coastal Flare

• Montauk Yacht Club: Sunset DJ with DJ Oli Benz
  On Sunday, August 31 (5–8 PM), experience the perfect seaside wrap-up at the Montauk Yacht Club, featuring waterfront tunes spun by DJ Oli Benz – great vibes, great drinks, and stellar sunset views.
• Gurney’s Resort, Montauk
  Wave goodbye to summer with style: Gurney’s Resort will host beach bonfires, live DJ sets as part of the Sound Waves Summer Music Series, and family-friendly Kids Club activities – making it a vibrant hub over the entire weekend.
• Marram Hotel, Montauk
  Prefer a more relaxed luxe stay? Marram is a boutique beachfront hotel offering private cabanas, ocean‑front yoga, and surfing lessons – ideal for those seeking a peaceful, stylish retreat

Quick Additions Table

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