Follow the trail of candy corn and pumpkin seeds to a slew of spooky events on the South Fork and Shelter Island this Halloween, which this year falls on a leaf-strewn Thursday (oh, to be a teacher on Friday, Nov. 1 — good luck with the sugar highs and lows, you good people; stay strong!).
Sag Harbor
It’s always a rollicking good time at Sag Harbor’s annual Ragamuffin Parade, which marches down Main Street in the old whaling village on Sunday, October 27. Sponsored by the Sag Harbor Chamber of Commerce, the beloved pumpkin trail of costumed tots (and grown-ups, too) — a tradition for over 30 years — starts at 1 p.m. at the corner of Nassau and Main streets between the Sag Harbor Launderette and Tutto il Giorno. Kids get to strut their costumed stuff and nab treats along the way safely from participating restaurants, shops and organizations marked by a pumpkin either on the window or door.
East Hampton
Head to the East Hampton Library at 159 Main St. for a full roster of multiple days of Halloween celebrations. Starting on Oct. 17, kids can create their best version of a ghostie apparition (in construction paper) from 4 to 5 p.m. — sign up here. On Thursday, Oct. 24, little ones can gather to make thumb-print bats in a host of Halloween-centric colors from 4 to 5 p.m. (perches secured here).

And for the big Halloween holiday moment: on Saturday, Oct. 26 from 10 a.m. to 5 p.m., there will be a multitude of seasonal shenanigans for the kids, they’ll need the entire afternoon to get through them all. Kids can take a spin through the Haunted Children’s Carnival and try their hand at pumpkin decorating (with a best carved pumpkin contest and best decorated skeleton contest to weigh in on, too), watch a family-friendly Halloween flick, hear tales of the Goody Garlick Witch Trial and the stories of those buried in the East Hampton Cemetery along with treats and other spooky surprises. Reserve your spot here.
Also at the East Hampton Library are a bunch of fun ghoulish movie nights, in varying levels of fright and fun: on Oct. 22 of the original 1922 Dracula-on-film silent classic, Nosferatu from 5 to 7 p.m. (reserve here); the animated fun-fest Monster House from 4:30 to 6:30 p.m. on Oct. 23, (reserve here); Scary Stories to Tell in the Dark on Oct. 30 from 4:30 to 6:30 p.m. (reserve here), and on Halloween proper get ready for a pecking scary session with Alfred Hitchcock’s winged 1963 classic The Birds from 5 to 7 p.m. (reserve here).
Pups like treats, too — bring yours (in costume!) to the 16 acre LongHouse Reserve (133 Hands Creek Road) for the annual Canines in Costume event, in collaboration with the Animal Rescue Fund of the Hamptons. Furry frolicking will be on the great lawn starting at 10:30 a.m. (bring bags, of course; you don’t want to leave tricks for your kind hosts) and sign-up requires a $25 to $35 fee — get your ticket here.
Bridgehampton
Head to the Bridgehampton Community House (2368 Montauk Highway) on Monday, Oct. 28 at 5 p.m. for the 26th annual pumpkin carving contest, hosted by the Bridgehampton Lions Club. Get your creative gourd juices flowing ahead of time (you are asked to bring your pre-carved pumpkin to enter the contest, which affords cash prizes from $30 to $400) to home in on the multitude of contest categories, including three new ones: Terrified Pets, How Does Your Garden Grow and (this should be interesting) Elon Musk. There’s also a puppet show by Liz Joyce and the Goat on a Boat Theatre, and those nice folks at Milk Pail are bringing the cider and donuts. Sweet! First place winners will receive $150, while second gets $100. Admission is free!
Shelter Island
On Wednesday, Oct. 23 at 2:45 to 3:45 p.m. the Shelter Island Public Library and Mashomack Preserve collaborate on “October Seedlings: Spooky Tales and Treats at Mashomack.” Kids ages 3 to 6 are welcome for an hour of ghostly stories, Halloween crafts and snacks and a spooky (but not scary!) look at surrounding nature. Reserve your little goblin’s place here.
On Shelter Island, the annual “Trunk or Treat” from 4 to 6 p.m. on October 31 at the parking lot next to the public tennis courts on Duvall Street will be back again for the best sugar-centric kids’ tailgate in town!). To sign up to be a grown-up, four-wheeled candy pusher at the event, email Barbara Marshall at [email protected].

Island kids can also head to Smith Street for the annual car-free candy-crush, where the community pools efforts to create a safe and fun trick-or-treating experience for all. The day concludes at 4 p.m. the Center Firehouse for hot dogs and other refreshments (so your kid isn’t just full of Snickers bars and Skittles).
Quogue
For the next two Saturdays and one Sunday — Oct. 19, 20 and 26 — you can hit the trails from noon to 2 p.m. with the Quogue Wildlife Refuge (3 Old Country Road) for their Enchanted Forest Trail. Costumes are encouraged for this super fun, seasonally inspired nature walk for kids ages 2 to 7 (accompanied by a grown-up ghoul, of course), where there will be games, activities, snacks and other refreshments for the kids before and after the hike. Bonus: Bring a reusable mug or water bottle and get a free sticker! Register here for this $10 per person event.
Hampton Bays
Books contain gifts on their pages that keep on giving — but the Hampton Bays Public Library (52 Ponquogue Avenue, 631-728-6241) has got loads of treats in store for Halloween, too. Most of their Halloween events are currently on a waitlist basis, but get your name on the roster and you may well be in for a seasonal slate of treats. On Thursday, Oct. 24, school age kids grades 3 to 6 make mummy mason jars, to create a unique, spooky light source for the darkening days ahead.
On Friday, Oct. 25, head to this gem of a community spot for their annual Halloween Parade & Trick-or-Treating event, where parents and guardians can bring costume-clad kids from the most mini to tween-age for trick-or-treating in the library from 4 to 5 p.m. starting in the Children’s Program Room.
Finally, on Oct. 28, wee ones (pre-school to grade 2) can gather to make their very own interpretations of that icon of Halloween, the witch. Paper plates, construction paper and other accoutrements will be supplied.