Long Island Pirate Festival
Saturday, September 19-Sunday, September 20
Brookhaven Amphitheater at Bald Hill
S. Bicycle Path, Farmingville

Have a little Jack Sparrow at home dreaming of becoming a pirate someday? Well, even if you don't, this festival has fun for everyone. With face-painting (eye-patches and beards of course), balloon sculptures, crafts, and fun foods, this is one kid-friendly festival you sure don't want to miss. Live music, a costume contest (so be sure and wear your best pirate gear) and dancing are reason enough to go, but last year my kids loved the live pirates walking around all day in full garb-who says Pirates don't exist? Check out the website by clicking here for more details. 

20th Annual Long Island Apple Festival
Sunday, September 20th
Serwood-Jayne House
55 Old Post Road, East Setauket, NY

To kick off the apple-picking season, East Setauket plays host to the Annual Apple Festival at the Sherwood-Jayne House. With fun old fashioned games like sack races, pony rides, and the famous apple pie baking contest, this is a really fun festival to celebrate traditional farm life. THere is colonial storytelling and tours of the Sherwood-Jayne house, an old family orchard farmhouse intact with original spaces and antiques. This is one of those great "step back in time" festivals that you can't find anywhere. Apart from great old fashioned fun, you can find apple cider and fritters which are to die for. Admission is $6 per adult and $4 per child, but it's worth it. Check out the Three Village Historical Society website for more information and times. 

17th Annual Italian Festival
Sunday, September 20th
Hofsta University South Campus
Hempstead

Greenport Maritime Maritime Festival
Village of Greenport, NY
Friday, September 18-Sunday September 20

And finally, to get a flavor of maritime culture, also what makes Long Island famous, head out to Greenport to the East End Seaport Museum's Maritime Festival. Starting with a parade, you can check out whaleboat races, a kayak derby, a clam chowder contest, and plenty of other festival activities. This festival is unique because the entire town jumps into the groove with retailers opening their doors and people literally roaming the streets enjoying the atmosphere while enjoying live music and entertainment that roams with them. The festival runs all weekend and you can see more information, including a schedule of events, here.