When you’re the founder of a project that involves 20,000 pies, 700 pie sellers, and 150 of the region’s best professional bakers, you have earned the right to brag. But David B. Waters, chief executive officer of Community Servings, would rather talk about it as a team effort. “We call it the world’s greatest bake sale,” he says.

“Pie in the Sky” is a bake sale par excellence. The Thanksgiving fundraiser is put on by Community Servings, a not-for-profit food and nutrition program that delivers delicious, medically-tailored meals to people struggling with life-threatening illnesses like cancer, HIV/AIDS and kidney disease. The program also feeds family members in those households. Since it was founded in 1989, the Jamaica Plain-based organization has served over 6 million free meals to individuals unable to cook for themselves and their families. “This is food that your grandmother might have made,” says Waters. “It evokes memories of a time when you felt safe and secure.”

Supporting the pie campaign is a snap. Place your order online at pieinthesky.orgby Nov. 21 and designate one of the more than 70 locations where you will pick up the dessert on the day before Thanksgiving. A $28 pie—available in apple, pumpkin, pecan and sweet potato flavors—generates proceeds to feed a critically ill person for a week. The campaign raises $750,000 to support the organization’s operation that feeds 1,000 people a day throughout eastern and central Massachusetts.

Waters, who grew up in Western Massachusetts and is a long-time resident of the Boston-Cambridge area, dreamed up “Pie in the Sky” years ago when he was general manager at UpStairs at the Pudding (which became UpStairs on the Square, now closed) in Harvard Square. “Friends were coping with the darkest days of the AIDS crisis,” he explains. He wanted to do something tangible to help, so he rallied colleagues in the restaurant industry to bake and donate pies to support Community Servings, where he was volunteering. The project grew from there, and is now replicated in multiple cities, including Philadelphia, New York and Denver.

David B Waters CEO of Community Servings
David Waters, CEO of Community Servings dreamed up the idea of Pie in the Sky years ago when working as a restaurant manager.
Courtesy of Community Servings

To fortify himself for the final push of the pie drive, Waters stops in at West Side Lounge, a favorite spot in his Cambridge neighborhood, and orders the butternut squash soup. Chef Arcesio Suarez first roasts the orange-hued squash, then purees it with vegetable stock, maple syrup, honey and a squeeze of lemon, before garnishing it with dried cranberries and an optional dollop of creme fraiche. Waters often brings to the restaurant his preschool-age son, who happily slurps down the soup. With a bowl this good, satisfying his little guy is as easy as pie.

Order your pie online atpieinthesky.org by Nov. 21 and designate your preferred pick-up location for Nov. 25.

Community Servings is located at 18 Marbury Terrace, Boston, info@servings.org, 617-522-7777, servings.org