Fall Festivals on the East End

While we are sad to see the summer come to an end, we are looking forward to the fall months here on the East End with numerous festivals and fun fall activities for the entire family to experience. Live music, food trucks, boat races, film screenings and countless kids’ activities are just a few of the things you can enjoy this fall in various towns across the Hamptons as well as the North Fork. Below are a few of our favorite festivals to check out on the East End this fall.


Harborfest | September 7 & 8
Harborfest, Sag Harbor’s annual festival celebrating the town’s maritime history, will take place on the first weekend in September. Enjoy everything nautical from a classic boat display on the wharf to the festival’s main event, the Whalers Cup whaleboat races. Shoppers can explore the arts and crafts fair in Marine Park as well as sidewalk sales along Main Street in the village. Live music will be performed on Long Wharf throughout the weekend featuring bands such as the HooDoo Loungers and Gene Casey and the Lone Sharks. Bay Street Theatre will host a special concert with The Complete Unknowns, a Bob Dylan tribute band, on Saturday evening as well. There will be plenty of activities for the kids including bounce castles, a corn shucking contest, and a tug-of-war competition.


Southampton Fest, September 20 through 22SouthamptonFest | September 20 -22
The annual SouthamptonFest will take over Southampton village September 20 -22 beginning with a kick-off cocktail party on Friday evening. The rest of the weekend will feature a wide variety of vendors and entertainment throughout the village. Agawam Park will be filled with food trucks, fine art vendors, a farmer’s market and the annual chowder contest will take place in the park on Saturday. Bands including Southbound and The Motown Band, among others, will be performing on the main stage in the park as well.  There will be a Kids Zone on the grounds of the Southampton Arts Center with many children’s activities including pumpkin decorating, face painting and a kids’ rock concert with Jim Turner. Take a horse and carriage ride around the village and enjoy all the sights of SouthamptonFest.


Greenport Maritime Festival, September 21 and 22

Greenport Maritime Festival | September 21 & 22
The 30th Annual East End Maritime Festival will take place in Greenport on September 21 & 22. After the weekend kicks off with a parade on Saturday morning, the streets of Greenport will come alive with artisan food and craft vendors, live music, and all kinds of entertainment for the entire family to enjoy. Saturday afternoon will feature kayak races and a helicopter rescue demonstration by the US Coast Guard and Sunday’s entertainment will include a chowder contest and an Irish step dancing performance. You can also enjoy the beauty of Greenport by boat with water tours offered by Mystic Whaler Cruises and Glory Harbor Tours. If you are bringing the kids, be sure to visit the Captain Kids Corner with a variety of activities for the younger crowd.


San Gennaro | September 28 & 29
The 9th Annual San Gennaro Festival will be held September 28 & 29. Good Ground Road in Hampton Bays will be lined with food trucks and vendors selling jewelry, clothing and more. The Hampton Bays Fire Department will host a small carnival with rides for the kids to enjoy and there will be fireworks on Saturday evening. The main stage will feature live music throughout the day, with concerts by several bands including The Ronald Reagans and That 70’s Band. This festival will also celebrate everything Italian with pizza, cannoli, and meatball eating contests.


Hamptons International Film Festival, October 10 - 14

Hamptons International Film Festival | October 10 – 14
One of the most popular fall events on the East End is the Hamptons International Film Festival, which will be held October 10 – 14 throughout the Hamptons. In its 27th year, the film festival showcases more than 100 of this year’s best films from around the world. Past guests at the festival include Julie Andrews, Alec Baldwin, and Billy Joel among many others. Visit their website for more information on schedules and purchasing tickets.


Westhampton Beach Oyster Festival | October 12
Westhampton Beach will be hosting its annual Oyster Festival on Saturday, October 12 at the Westhampton Beach Marina. While the main focus of this festival will be on the oysters there will also be craft beer, wine, and numerous other food options for all to enjoy. Entertainment will include live music and various kids’ activities as well as a pirate show by Kings of the Coast. This event is one day only, so be sure to mark your calendars.


Montauk Fall Festival, October 12 & 13

Montauk Fall Festival | October 12 & 13
One of the longest running East End festivals in its 38th year, the annual Fall Festival in Montauk, will be held over the holiday weekend as well, October 12 & 13. The entire event is held on the Montauk Village Green and will feature live music, Long Island beers and wines, Octoberfest foods and a farmer’s market. You can also enjoy free carousel rides throughout the weekend. There will be a clam chowder contest on Saturday beginning at 11 am and a Chinese auction drawing and Cash Catch drawing will be held on Sunday to close out the festival.

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