On the evening of Nov. 25, the Boston Convention and Exhibition Center was alive with holiday cheer as 30 volunteers and program coordinators formed a well-oiled pie-prepping machine for the annual Pie in the Sky fundraiser.

Held each Thanksgiving season by Community Servings, a Jamaica Plain-based nonprofit, over the course of two hours, more than 2,000 pies were prepped for distribution across Massachusetts. Volunteers maneuvered between tables with impressive stacks of pies ready to be sorted and inspected. 

“We receive pies that are baked by restaurants, caterers and other businesses … and we take a look at them, make sure that they’re up to snuff,” said Deva Djaafar, a volunteer and logistics coordinator for onsite volunteering. 

Pie in the Sky has been around for 32 holiday seasons. David Waters, CEO of Community Servings, started the event to ensure that people who have specific dietary needs have access to nutritious, medically-tailored meals. It began as a grassroots bake sale that funded the organization’s work of preparing and delivering hot, nutritious meals to individuals living with HIV/AIDS in Dorchester and Roxbury, according to the organization’s website. At Pie in the Sky, each pie sale provides a week of hot meals for someone in need.  

“There are over 100 pickup sites around the state where people can pick up their pies,” Djaafar said.

If people order more than one pie, or maybe a pie with a Community Servings-branded hat, those specialty orders will be delivered to the Exhibition Center in Seaport. There, the pies will be inspected and sorted by at least three or four volunteers to ensure the pies make it to the correct pickup locations. 

 “A lot of those [pickup sites] we send pies directly to, but there are some that require special handling,” said Ryan Levasseur, director of communications at Community Servings. Preparation for this annual event begins as early as August, with Levasseur organizing everything from marketing campaigns to community outreach. 

“This is a peer-to-peer fundraiser, meaning members of the community sign up to sell pies,” Levasseur said. “They sell pies to their networks — family, friends, colleagues — using social media, email and word-of-mouth. It’s a grassroots effort to engage the community and explain how purchasing a pie helps fund the work we do.”

In addition to networking amongst members of the community, the Pie in the Sky fundraiser relies on the efforts of volunteers to see to it that all of the pie orders are properly sorted and delivered to the right drop-off locations in a timely manner.   

Beth Gustin, a returning Pie in the Sky volunteer, enjoys dedicating her time to helping out her community, especially during the holiday season. 

Keeping families well-fed “means the world” to Gustin, she said. “This is what the holiday season is all about — giving back.” 

Kelly Bunting has volunteered for Pie in the Sky for five seasons and values the accessibility of the volunteering event. 

“It was really, really convenient. You can just pick a time to do this on the website, and every time I’ve done it, I’ve had a lot of fun,” Bunting said. 

Bunting also said Community Servings has grown greatly since her first time volunteering.  

“I remember being in a facility in Dorchester, helping actually make the pies,” Bunting said. “Now it’s just a huge, large-scale operation.” 

This high-energy, extensive operation is much more than pie preparation; it’s about bringing people together to support a meaningful cause. 

“It’s much more complex, what we do now — it’s very rigorous in terms of the scientific approach,” Levasseur said.

Since its creation in the early ‘90s, with the help of over 500 volunteers and over 150 Boston-area chefs, bakers and caterers donating Thanksgiving pies, Pie in the Sky has been able to grow the quality and reach of its operations, securing critical funding for the expansion of its nutritional meals program. Pie in the Sky now has a fundraising and research development team, registered nutritionists and client services and a culinary crew. It also has its own kitchen in Jamaica Plain where its meals are made from scratch. 

Each pie is sold for $35, which is the cost to provide one week of medically-tailored meals to someone in need. 

“For $35, we give you a pie to enjoy at home on Thanksgiving and you get to slice into that pie knowing that you helped give a week of meals to a neighbor in need in Massachusetts or Rhode Island,” Levasseur said. “It’s remarkable.”

This season, Pie in the Sky is expected to sell 20,000 pies and will fundraise nearly $1 million that will directly support the nutritional meals program at Community Servings, according to Levasseur. 

“People get a lot of satisfaction from being here. They know they’ve done something impactful,” Djaafar said. “Some volunteers come every year. It’s their tradition. Others are first-timers, and it’s amazing to see their reactions when they realize how much their work helps.”