Celebrate Seasonal Fun at East End Fall Festivals

One of the many colorful displays at the 2019 Riverhead Country Fair Photo by David Taylor

As the heart of autumn approaches, it’s time to take pleasure in everything another exciting season has to offer in the Hamptons and on the North Fork. Fall on Long Island is a wonderful time for celebrations filled with family, food, music and art. This year, a number of festivals are steeped in the harvest spirit. Here’s a rundown of what’s coming.

Waterdrinker Farm Fall Festival
October 1, 10 a.m.–5 p.m.

This excellent event kicks off October  with a guaranteed great time picking pumpkins and sunflowers in Waterdrinker Farm’s vast fields. Additional activities include mini-golf, barnyard animals, a jumbo jump pad, roasted corn and tractor pedal cars. $15 adults/ free for kids under 2. 663 Wading River Road, Manorville. water-drinker.com/fallfestival

North Meets South – Farms, Food & Drink Festival
October 2–3, 10 a.m.

This annual festival in Downtown Riverhead features giant yard games, henna tattoos, face painting, balloon art twisters and farm animals in a new Vibes & Chill Entertainment Space. North Meets South provides a place to connect and network with food trucks, farmers, craft artisans, restaurants, vineyards, breweries, cider houses, artists, children’s entertainers and a variety of other businesses from across Long Island. Peconic Riverfront, Downtown Riverhead. northmeetssouthfestival.com

Hamptons International Film Festival
October 7–13

Attend screenings and world premieres of a unique collection of international films at this year’s Hamptons International Film Festival. This longstanding annual movie extravaganza features films offering fresh and different global perspectives to educate audiences, shorts and entertaining feature films. Contact the box office online for tickets to as many or as few films as you’d like. Screenings at Guild Hall in East Hampton (158 Main Street) and Sag Harbor Cinema (90 Main Street). hamptonsfilmfest.org

Famous Food Festival “Taste the World”
October 9, 10 a.m.

Featuring many activities including live music, beer and wine garden, virtual reality, rock wall, butterfly exhibit, art tent and painting at Tanger Outlets in Riverhead, the Famous Food Festival “Taste the World” event is offering culinary delights from more than 70 vendors! Tanger Outlets, 1770 West Main Street, Riverhead. facebook.com/events/6035423656483205

The Montauk skyline for Fall Festival Weekend
The Montauk skyline for Fall Festival Weekend

Montauk Fall Festival
October 9–10, 11 a.m.–5 p.m.

Join in commemorating the 40th year of the Montauk Fall Festival with pumpkin painting, kid crafts, bouncy rides, a phenomenal food tent and live entertainment from Joe Delia and the Thieves. Farmers market vendors will also line the street both days. On Saturday, the festival will host their annual chowder contest. Montauk Village Green. montaukchamber.com

Kids stomp grapes at the Wölffer Harvest Party
Kids stomp grapes at the Wölffer Harvest Party. Photo credit: Brendan J. O’Reilly

Wölffer Estate Annual Harvest Party
October 9, noon–4:30 p.m.

Celebrate the annual grape harvest with many fun activities, including a winemaking relay race, barrel-rolling, grape-stomping, hayrides and pony rides. A vast menu of dishes by Palo Santo, Pizza Luca and Fresh Flavors will be served, and live music will bring additional cheer. $165 adults/ $155 wine club members/ $85 kids 3–20/ free kids under 2. 139 Sagg Road, Sagaponack. wolffer.com

Brazilian BBQ Festival ’21
October 9, 1 p.m.

Brazil comes to the Hamptons. Enjoy a classic Brazilian barbecue with food, beer, cultural presentations and a live band and DJ. $50–$75 Regular Admission costs $120, $150 VIP. 125 Tuckahoe Lane, Southampton. allevents.in/mobile/amp-event.php?event_id=10000169857738067

L.I. Antique Power Association tractor display, Photo: Courtesy Riverhead Country Fair
L.I. Antique Power Association tractor display, Photo: Courtesy Riverhead Country Fair

45th Annual Riverhead Country Fair
October 10, 10 a.m–5 p.m.

The 45th annual Riverhead Country Fair returns with carnival rides, craft vendors, midway games for kids and delicious food. Also peruse agricultural, homemaking and needlecraft exhibits, and join numerous competitions in a wide range of categories that welcome participation. Main Street, Downtown Riverhead. riverheadcountryfair.com

Halloween Fest
October 23, 11 a.m.

Watch in horror as Downtown Riverhead is transformed into a spooky and ghostly scene for Halloween Fest! Take part in all sorts of spooktacular activities throughout the weekend, such as a Haunted Ale-Trail at local breweries, performances at the Suffolk Theater, coffin races on Griffing Avenue, trick-or-treating, and the famous Goblin Parade down Main Street. Community members, organizations and businesses are also invited to decorate a lamp post along Main Street with Halloween and fall-themed accoutrements. (Rain date: October 24.) Main Street, Downtown Riverhead. downtownriverhead.org/halloween-fest

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