Montauk Music Festival (Mid-May (2026: May 14-17)). 15th annual free festival in 2026; 100+ acts across 40 Montauk venues with 400+ performances including the Main Stage at Montauk Lighthouse.
Invasion of the Pines (Fire Island) (July 4 (annually)). Annual Fourth of July celebration in which hundreds of drag queens from Cherry Grove sail to Fire Island Pines Harbor, drawing thousands of spectators. Tradition began 1976.
Hampton Classic Horse Show (Late August (annually, Bridgehampton)). One of the largest outdoor horse shows in the USA; approximately 1,500 horses and 200+ competitions. Held at 240 Snake Hollow Road, Bridgehampton.
Greenport Maritime Festival (Late September (annually, Greenport Village)). Annual celebration of the North Fork's maritime heritage at the East End Seaport Museum; includes a Merfolk parade, cardboard boat regatta, live sea shanties, and street fair.
North Fork Wine Harvest Season (September-October). Long Island Wine Country vineyards host barrel tastings, vineyard walks, harvest dinners, and oyster showcases throughout fall across the North Fork AVA.
Hamptons International Film Festival (Early October (2026: October 2-12)). 34th annual festival in 2026; screenings and events across the East End Hamptons communities.