Mikaela Marrero in last year’s holiday photo, when she was...

Mikaela Marrero in last year’s holiday photo, when she was 3 years old.   Credit: RoMaRo Photography

When Alissa Orlando dressed her family in red-green-and-white plaid Christmas pajamas on Oct. 8 and posed with them for photos, she thoroughly confused her 5-year-old son. “Why are we taking Christmas pictures? It’s not even Halloween yet,” she says Christopher asked.

“I tried to make it like a game. ‘Santa’s reindeer and elves have been resting. Santa needs our help to get the magic ready so the reindeer can fly, and the elves can start making their toys in their workshop,’” she told Christopher. He bought it.

In reality, Orlando, a 33-year-old elementary school teacher from Nesconset, and her husband, Chris, 37, a police officer, booked the photo session in October for entirely different reasons.

Caroline Golio, of Wantagh, schedules her family holiday photos for...

Caroline Golio, of Wantagh, schedules her family holiday photos for October every year; she’s already finished with this year’s shoot, which was done outdoors with a holiday bedtime scene.  Credit: Siobhan

One, no way would their children smile and cooperate outdoors in pajamas if they were freezing — they also have a 3-year-old named Alexander. And two, Orlando wanted proofs in time to order and mail their 60 holiday cards by Dec. 1.

For Long Island families who plot out their holiday photo scenes year after year, mid-October to mid-November ’Tis The Season, especially because so many of the photos are staged outdoors with elaborate backgrounds — vintage cars, pine tree borders, Hanukkah doughnut shops and at least one Long Island photographer who offers holiday portraits shot with a horse.

MINI-SESSIONS, MAXI FUN

Photographers call these “mini-sessions,” and charge families from $150 to $300 for a 15-to-20-minute session, which will include a certain number of poses and sometimes even a change of outfits, local professional photographers say. The photographers line up the sessions back-to-back.

Alissa Orlando, her husband, Chris, and their children, Alexander, 3...

Alissa Orlando, her husband, Chris, and their children, Alexander, 3 (left), and Christopher, 5, of Nesconset, had their holiday photos shot in October 2022. 

Sometimes shoots are done at local parks or Christmas tree farms on the East End. And some businesses offer families the chance to take photos with their own cameras. Ali Kusinitz of Sign Gals of Long Island, for instance, offers a Christmas backdrop and a Hanukkah backdrop in her Plainview backyard, and people pay $25 per person and $5 for each additional person to spend 10 minutes shooting their own pictures.

Professional photographers have fun at the shoots, says Rosangela Roque-Ortiz of RoMaRo Photography in St. James. "A lot of the families come back to me every year, so I get to see the kids grow up."

That's the case with Mikaela Marrero, 4, of Deer Park. "She took the first Christmas pictures of my daughter," Mikaela's mother, Martha, 46, who works for Estee Lauder says of Roque-Ortiz. She's returned for the past three years. Last year Marrero chose to have the photos taken on the one day each season that Roque-Ortiz hires a Santa Claus to add to the charm of the photographs. "He was such a fun guy. The props were beautiful, the backdrop was absolutely gorgeous. My daughter loved it," she says.

NO RUNNING NOSES, PUFFY COATS

Orlando had her 2022 photos shot by Amityville-based photographer Siobhan Becker of Photos by Siobhan, who rented a bed and a fireplace mantel and set the scene in her mother’s backyard. Becker says photographers like to offer holiday shoots in October and November because they need the longer days of light to get multiple appointments in during weekend days when families have time, and they need opportunities for backup rain dates if a weekend brings stormy weather. Also, as Orlando mentioned, the cold. Red running noses, tears streaming down faces and puffy winter coats don’t make for great images, she says.

Last year, Kaitlin Rodgers of Selden had her daughters’ holiday...

Last year, Kaitlin Rodgers of Selden had her daughters’ holiday photos shot in October. Pictured are Harper (left) and Charlotte.   Credit: Charity Vaz Photography

Because Long Island is, well, an island, some families even get their photos taken as early as the summer at Long Island beaches. “I did my photos in July this year,” says Kaitlin Rodgers, 27, of Selden, a travel agent who has three daughters, ages 4, 2 and 8 months. She and her husband, Kevin, 28, who works for the Long Island Rail Road, dressed the family in denim and white and had the photos shot in front of the Fire Island Lighthouse by Bohemia-based photographer Michael Cassara. She says her gifts to family members are always pictures of her children, and shooting photos early gives her time to receive her edited photos from the photographer, choose which images she likes best and then order gifts from websites such as Shutterfly or Easy Canvas Prints.

Last year, Rodgers had her photos of her two older daughters taken in an indoor holiday baking scene setup offered by Bellport based photographer Charity Vaz. One of Rodgers’ daughters has autism, and Rodgers says Vaz “worked really well with my daughter. She’s got the patience for it.” Vaz also has an autistic child and specializes in photographing children with disabilities. “I start taking Christmas photos the first weekend in October,” Vaz says. She will do 15 to 30 families in one weekend.

SHORT AND SWEET(S)

Katie Rodgers had her family holiday photos shot at a...

Katie Rodgers had her family holiday photos shot at a “mini-session” at the Fire Island Lighthouse in July. 

The short session times work out well, parents and photographers say. “It sounds like it’s not very long, but kids, they can’t really last longer than that,” Orlando says.

Adds photographer Cassara, “There’s a lot of bribery that goes on in photo shoots. It usually comes down to bribing them with sweets.”

Caroline Golio, a teacher from Wantagh, says she needs no such added incentive to get her photos done early in the holiday season. “It just alleviates the stress,” says Golio, 32. “We all pack into the car, including the dog.” She and her husband, Robert, 35, a vice president small business specialist, have a son, Robbie, 2, and a golden retriever named Moose.

Robbie is more relaxed when the family devotes a day to the photo shoot without other obligations, which translates to better pictures, she says. Golio’s favorite photo this year is her son jumping up and down on a holiday-themed bed. “It looks like it should be in a holiday magazine, it was so natural,” she says. She also likes to use a “blooper” shoot on the back of her holiday cards, embracing the outtakes.

Arranging photos early means that when the peak hustle-and-bustle of the holiday season hits around Thanksgiving, Golio has one thing already checked off her seasonal to-do list. And that is a holiday gift to herself.