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The Bridgehampton Lions Club’s annual pumpkin carving contest is on Monday at the Bridgehampton Community House. (Photo courtesy of Bridgehampton Lions Club)

Trick-or-treating on Shelter Island is an annual affair, starting at the Center Firehouse tomorrow afternoon. (Photo credit: Amanda Bartilucci)

Even though Halloween falls on a weekday this year, the spooky spirit amongst South Forkers remains stronger than ever. Today and tomorrow businesses and organizations scattered around the Hamptons will host events in honor of All Hallow’s Eve with trick-or-treating, pumpkin carving contests, costume parties (for all ages), a tiny barbecue and fun for the whole family.

Tonight at 5 p.m. it’s the 25th annual carving contest, hosted by the Bridgehampton Lions Club. With the Bridgehampton Community House serving as the event’s location, participants are invited to bring their pre-carved pumpkin and enter it to win some pretty sweet cash rewards! There are several themed categories for carvings that all age groups may participate in. First place winners will receive $150, while second gets $100. Additionally, there’s the 13 and under freestyle categories where the first place is awarded $150, second gets $100 and third will receive $75. In the master blade freestyle first gets $400, while second and third will receive $250 and $150, respectively. Pumpkins must be already carved BEFORE entering. Also, guests may enjoy a puppet show from Goat on a Boat Theatre, plus cider and donuts provided by the Milk Pail. Admission is free!  

The Westhampton Chamber of Commerce hosts a Halloween party for kids at Glovers Park tomorrow from 3:30 to 5:30 p.m.. Aside from the highly desired candy, there’ll be dancing and festive games with a live DJ.

Businesses participating in the annual Sag Harbor Pumpkin Trail tomorrow afternoon will be marked with this sign either on the door or window. (Photo courtesy of Sag Harbor Chamber of Commerce)

Sag Harbor’s annual pumpkin trail takes place on Halloween proper from 3 to 5 p.m. on Main Street. According to Sag Harbor Chamber of Commerce president Ellen Dioguardi, the pumpkin trail is a safe and fun trick-or-treating experience that’s gone on for decades throughout the village’s business district.

“The pumpkin trail is a personal favorite chamber event of mine,” she says. “What’s more fun than handing out candy to smiling kids in costumes?” Kids of all ages are welcome to travel up and down Main Street to trick-or-treat along the pumpkin trail, with participating restaurants, shops and organizations marked by a pumpkin either on the window or door.

“What began as a fun way to get more people into the village over 30 years ago has become a Halloween tradition for Sag Harbor area families,” says Dioguardi. “I love when parents tell me they remember doing the pumpkin trail when they were young. It’s all about community and the chamber members are great about supporting this event.”

Just a quick ferry ride away, on Shelter Island, a similar trick-or-treating scenario will take place tomorrow afternoon. Starting at 4 p.m., trick-or-treaters on The Rock will gather on Smith Street for the annual candy-palooza, and continue down School Street. According to resident and Shelter Island Chamber of Commerce member Amanda Bartilucci, the late Chrissy Gross — who sadly passed away in September — started the tradition, which includes a candy drive organized by the Shelter Island High School’s National Honor Society. “It’s a total community effort,” Bartilucci says. “It’s a really safe way kids in our community can celebrate,” she says, noting consolidating trick-or-treating into one spot makes it easier on both the families and the community as a whole. Afterward, there’s a small reception at the Center Firehouse where there’ll be hot dogs and other refreshments.

Trick-or-treating is on School Street on Shelter Island tomorrow afternoon. (Photo credit: Amanda Bartilucci)

Also tomorrow, at the parking lot next to the public tennis courts on Duvall Street, keep your eyes peeled for the Shelter Island Parent Teacher Student Association’s Trunk or Treat, a new-ish annual event where residents park, decorate their car trunks in Halloween regalia and give out candy in one fun spot. (Bonus: Chequit pastry chef Mazie Galle makes a bevy of fun confections to give out!). And starting at 10 a.m., kids of all ages are welcome to a spooky walk through the Shelter Island Public Library. Visitors can creep through the library’s house of horrors, if they dare, for some frightful scenes.

All day tomorrow at the Quogue Library everyone is welcome for some costume fun. Dress up in a Halloween costumes and receive raffle tickets toward a especially spooky prize basket.