Maritime Festival - Greenport, NY - Sep 18 to Sep 20, 2020
Celebrates the nautical history of Greenport Village. Tall ships, demonstrations, live music, vendors, and food. Hosted by the East End Seaport & Marine Foundation in partnership with the Village of Greenport.
Sag Harbor American Music Festival - Sag Harbor, NY - Sep 24 to Sep 27, 2020
Non-profit festival includes a Main Stage concert and fundraiser featuring internationally known performers and two days of FREE music with dozens of acts across several genres and in several local venues.
Montauk Fall Festival - Montauk, NY - Oct 10 to Oct 11, 2020
Live music, Long Island beers, free carousel, foods, contests and plenty more.
Taste of the Catskills - Delhi, NY - Oct 10 to Oct 11, 2020
This festival showcases the food, beer, crafts, and wine of the region. Plenty of kids activities, plus cooking workshops, live entertainment, Catskill Puppets, celebrities and a Farm Olympics competition. The festival ends with a harvest dinner and bonfire.
Long Island Oyster Festival - Oyster Bay, NY - Oct 17 to Oct 18, 2020
This is a huge festival with over 200,000 attending this two day event. It features the tall ships, midway rides, pirate shows, oyster eating and shucking contest, food court, and lots of live stage entertainment. Free parking and free admission, and the profits from many activities including the food court support local charities.
Halloween Harvest Festival - Long Island City, NY - Jan 1 to Oct 26, 2019
Canceled for 2020, look for their return in 2021. Normally: A free harvest festival held at Socrates Sculpture Park. Past years included theme specific activities and performances, plus Socrates Halloween traditions like spooky costume and art making, face painting, costume contest and more.