Annual Pie in the Sky Fundraiser Aims to Raise More Than $750,000 for Medically Tailored Meals

Community Servings is gearing up for its 29th annual Pie in the Sky fundraiser, which raises money for the organization to make and serve meals to chronically ill people across the state.

“Community Servings has been feeding critically ill residents of Massachusetts for 31 years, and during that time, for the past 29 years, we have hosted an annual Thanksgiving pie sale called Pie in the Sky, which offers people in the community the opportunity to buy a beautiful Thanksgiving pie and support our program to feed neighbors who have nowhere else to turn for their food this holiday season,” Community Servings CEO David Waters told the Gazette.

Whole Foods is sponsoring the fundraiser again this year, and will be selling “Pie in the Sky” pies across all of its Massachusetts stores from November 15 to November 30. A donation of $5 from each of these pies will be made to Community Servings.

Despite the pandemic, the sale was held last year with some changes. More than 7,000 pies were distributed, bringing in more than $640,000. Community Servings said this year it hopes to double the number of pies sold and raise more than $750,000 towards its meal program.

“It probably won’t be our largest year because of COVID,” Waters said of this year’s sale, as “we had to shrink the program for safety’s sake.”

Though the pandemic has presented many challenges, Community Servings volunteers found a way to still hold the fundraiser while keeping all participants safe. Last year, all pickup sires were outdoors, Waters said, and this year, there will be a mixture of indoor and outdoor locations.

Additionally, the fundraiser typically involves 200 to 300 volunteers in the same room, but that that could not be done this year. “Our committee of volunteers worked really hard to redesign the system to make moving 14,000 pies around the state work without any COVID risk,” Waters said. “We have very dedicated volunteers who have been doing this for years and years and they are determined, that despite the pandemic, the pie sale would continue.”

When a pie order is placed, the purchaser can decide where they want to pick it up on the Tuesday before Thanksgiving.

Waters said he is especially excited about this year’s sale “because as a society, as a community, we’ve gone through so much trauma and so many things in our lives,” but “to have something that celebrates the good of the community and the importance of Thanksgiving and the generosity of the community I think is so affirming. I think everybody who’s involved in Pie in the Sky really thinks about it as being part of their holiday tradition.”

Community Servings feeds more than 1700 people a day, so “donations are so important to our ability to continue to ensure that we can continue to deliver meals throughout this winter,” Waters said.

The pies are traditionally baked by more than 150 chefs, bakers, and restaurants in the Boston area, according to Community Servings, but because of the challenges brought forth by the pandemic, they will all be baked by Boston Baking and 11 different restaurants this year. Pie choices include apple, pecan, or pumpkin, and each pie will cost $30, which will pay for meals for one Community Servings client for a week. Pies need to be picked up at their pick-up site on November 23.

Pickup sites in the Back Bay, Beacon Hill, and South End include the Copley Square Farmers Market, the Coldwell Banker location on Boylston St., the Whole Foods at the Charles River Plaza, and the Coldwell Banker location on Tremont St.

The restaurants that will be baking the pies this year are: Davio’s Northern Italian Steakhouse, Flour Bakery, Mistral, Mooo, Ostra , Grill 23 & Bar, Harvest, The Banks, America’s Test Kitchen, Basil Tree Catering, and Blue Frog Bakery

Other sponsors of this year’s Pie in the Sky are Big Foot Moving & Storage, Boston Baking, Coldwell Banker Cares, Digitas, Ligris & Associates, ScrubaDub Auto Wash Centers, State Street, and Tito’s Handmade Vodka.

Community Servings said that ScrubaDub will provide complimentary car washes to those “who support the Pie in the Sky Campaign with a ‘Pie for a Community Servings Client’ donation.’”

Waters said of the fundraiser, “we joke that it’s the world’s greatest bake sale,” as it consists of many hands coming together in various ways, whether it be baking pies, selling pies, or working at one of the pickup sites.

“Everybody has a role to play and I think it ties back to really the meaning of Community Servings, which is the community serving the community,” he said. “I find it to be a high to see how many people care to participate in Pie in the Sky as part of their holiday tradition.”

For more information and to order a pie, visit

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