5 Fall Festivals You Can’t Miss on Long Island

Pumpkins and hayrides and apple cider doughnuts—oh my!

It may feel like every other town hosts a fall festival, replete with apple cider donuts and obligatory street vendors—and that’s perfectly ok. But if you’re starting to feel overwhelmed by the vast possibilities lain out before you, never fear. There’s hope for organizing your weekend plans yet. Read on for the top five Long Island fall festivals.

Harbes Family Farm’s Pumpkin Festival

This annual, two-day festival marks the beginning of pumpkin season. Mattituck’s Harbes opens their barnyard pumpkin patch during the last weekend of September, offering seven acres of “u-pick” pumpkins, concession stands, Harbes Vineyard wines, donut-eating contests, games, pumpkin rolling competitions, potato sack races, tug-of-war, and scarecrow dress-up relays. Singing hayrides and free live music round out the entertainment. Parents can shell out a little extra, too, and introduce their kids to the Harbes Barnyard Adventure, an eight-acre “farm” filled with animals and activities. Admission to the general festival is free, although the barnyard and singing hayrides are extra.

Harbes Family Farm Pumpkin Festival, 25 Sound Avenue, Mattituck, September 29 through September 30, 10 a.m. to 6 p.m., free. 

Montauk Fall Festival

This year, the Montauk Fall Festival will celebrate 37 years of excellent chowders.

This year will make the 37th anniversary of the Montauk Fall Festival, hosted by the Chamber of Commerce over the Columbus Day weekend. The festival is an ode to fall, featuring live music, a farmer’s market, a 30-horse carousel, local beers and wines, and Oktoberfest foods, but the festival’s crowning jewel is the Saturday Clam Chowder Contest, in which patrons can buy mugs (each good for two tastes) in order to judge the red and white clam chowders of local Montauk establishments. It is, for good reason, one of the highlights of the off-season, but you’ll want to arrive early to claim your cup (and chowder), since lines are long and the contest officially ends once the ladles have run dry.

Montauk Fall Festival, Montauk Green, Montauk, October 6 through October 7, 11 a.m. to 5 p.m., free. 

Spooky Fest

Halloween enthusiasts will not want to miss out on the weekend fun at Rockville Centre’s Center for Science Teaching and Learning, where, on October 13, 14, 15, 19, 20, 21, 26, 27, and 28, the 16-acre Tanglewood Preserve will be converted into a spooky dreamworld. Attendees can enjoy mazes through the haunted woods, a live animal exhibit, face painting, crafts, and more. Adults can wade through the woods in search of spook-tastic food trucks, which will be hawking tons of delicious and not-so-scary edible creations. Admission prices differ depending on what package you choose ($10 gets you into about half of the exhibits, while $15 covers everything offered, save for food). It’s an ode to Halloween if ever there was one.

Spooky Fest, The Center for Science Teaching and Learning, 1 Tanglewood Road, Rockville Centre, Fridays, Saturdays, and Sundays in October, beginning October 13, 6:30 to 9:30 p.m., $10 to $15. 

Islip County Fair

This is your chance to make a new tradition.

New in 2018, the Islip County Fair is looking for a place on the map. This mid-island event will feature live entertainment, line dancing, a pumpkin patch with pumpkin decorating, roasted corn, and concessions. Participants can sign up for a children’s costume contest and parade, or try their hands at a pie-eating contest (proceeds go to charity). There will be plenty of child-friendly activities, like face-painting, as well as delicious fall-themed snacks for adults in attendance. The Chamber of Commerce hopes to make the fair a yearly tradition.

Islip County Fair, 401 Main Street, Islip, October 27, 11 a.m. to 5 p.m., free. 

The Great Jack-O-Lantern Spectacular Sail

The Great Jack-O-Lantern Spectacular Sail is an event worthy of its spectacular name. 

Belmont Lake State Park will host the 6th annual Great Jack-O-Lantern Sail, featuring a flotilla of carved pumpkins. The first 50 pumpkins received will be sent into the lake, lit by candle, and trailed by kayaks (for safety’s sake, of course). A “spooky den,” or child-friendly take on a haunted house, will be at the ready, as will crafts, games, inflatables, photo stations, and, naturally, candy. At twilight, the lit, floating pumpkins make for a truly spectacular sight, one of the absolutely must-see spectacles of autumn on Long Island.

The Great Jack-O-Lantern Spectacular Sail, Belmont Lake State Park, Belmont, October 27, 3 to 6 p.m., free.