Christmas in the City is 100% volunteer organization with a strong ethos of community caring for community.

It’s December 1988. Jake and Sparky Kennedy’s family’s growing. The stockings are hung by the chimney with care – and stuffed. The tree is ringed with more toys and gifts than the kids will ever use. While the house is filled with joy, Jake and Sparky feel something’s missing: how to make sure their kids can experience not only the joy of receiving gifts, but the spirit of the season: kindness, goodwill, sharing with others. As Jake puts it, “showing the kids that it wasn’t just all about them”.

It’s December 1989, and a new family tradition begins. With friends, co-workers, and clients of Kennedy Brothers Physical Therapy volunteering their time and donating gifts and money, Christmas in the City is born. That first year, 165 mothers and children from Boston homeless shelters are guests at a party at Boston City Hall, complete with festive decorations, games, a holiday meal and a gift for each child that the child had asked Santa to deliver.

Since that first party, Christmas in the City has grown. Today, the party – a truly magical experience – hosts thousands of children (and their parents) from Boston-area homeless shelters. The day after the party, they run Monday Mania, at which thousands of toys and gifts are distributed to families who aren’t experiencing homelessness, but live on the edge of poverty.

And they do 100% of everything with volunteers, a roster 2,500+ strong, including many of the kids who attended a party and come back to CITC as volunteers, and many volunteers who’ve been with us since way back in 1989. All four Kennedy children, whose 1988 Christmas inspired Jake and Sparky to start Christmas in the City, have volunteered over the years. And in 2018, Chip Kennedy branched out and began Christmas in the City, New York.


Christmas in the City

In December, CITC throws a party for 6,000 kids and family members from families living in Boston area shelters. And what a party! An extravaganza featuring:

  • A red-carpet welcome parade
  • Live entertainment – including the Blue Man Group
  • Costume characters
  • Games
  • An indoor amusement park
  • A petting zoo
  • Tons of kid-friendly activities
  • Plenty of goodies to eat

Each child gets a visit with Santa, who makes sure everyone gets:

  • A personalized gift from their wish list
  • A backpack or shopping bag full of toys, stocking-stuffers, hats, mittens, gloves, t-shirts, books…

And there’s always a little something for the grown-ups, too.

They offer the things that most of us take for granted, but are often hard to access when you’re living in a shelter:

  • Health Screenings
  • Dental screenings
  • Flu shots
  • Haircuts

Why go all out? Because these children and their families deserve a day that’s all about being welcomed and cherished, joyful, and worry-free. Their guests tell them that the party is:

  • A magical experience
  • A blessing
  • A day filled with joy
  • The best day of their lives
  • A life changer

And the 2,000 volunteers who staff the party tell them the same things!


Halloween in the City

A long time volunteer who grew up in Boston’s inner city, was always bothered by one thing: kids don’t go out trick or treating in their own neighborhood. It’s just too dangerous.

In 2018, he decided to do something about the absence of trick-or-treating in his neighborhood. He worked with other Christmas in the City volunteers to set up a block party for kids in the Dorchester/Roxbury section of Boston. Now those kids are scurrying around in their own neighborhood, collecting candy. They’re out at night having a fun time with their friends, and it’s safe.

Now, not a week goes by without one of his neighbors coming up to thank him for bringing trick-or-treat to their streets, and without some of the neighborhood kids asking him for assurances that it will happen again this October.


Job Fair

Each fall, the Job Fair is held at the Reggie Lewis Center at Roxbury Community College. This is in the heart of an underserved community, and that’s by design. The job fair should be accessible to all, especially those most in need of opportunities. They take care to make sure that there are organizations representing many different industries, and offering jobs at all levels that open up career paths.  Christmas in the City also makes sure that there are CORI-friendly companies participating, and tell job seekers which employers are CORI-friendly and which are offering ESL positions.

When job seekers first come in, they are invited to practice their handshake and pitch with CITC greeters, volunteers – all with extensive work experience.  Confident that they have one meet and greet down, and that they’ve worked out the kinks, job seekers enter the hall, where they have the opportunity to meet with more than 35 different hiring organizations and job resources.


Thanksgiving in the City

The Saturday before Thanksgiving, Christmas in the City becomes Thanksgiving in the City. On that day, CITC distributes hundreds of food baskets to families in need. Thanks to the generosity of their donors and corporate supporters, they’re able to fill those baskets with all the fixins’: turkey, potatoes, stuffing, gravy, veggies, as well as some stock-the-larder items.


Winter Wonderland

At a volunteer meeting in the Spring of 2017, Christmas in the City started brainstorming about fundraising for their programs. Someone wondered whether they could take advantage of the indoor amusement park that’s set up for the Sunday of the holiday party. Those rides, after all, are just sitting there the Saturday before… why not invite Boston area families to come on in and help support a terrific cause? What a great way to celebrate the holiday season. A volunteer put her hand up and agreed to run with the idea.

For $20 a ticket, kids have unlimited access to 20 great rides – and all proceeds go to support Christmas in the City.  They make the day even more special with carolers, crafts and pictures with Santa. They ask the families who come to share in the spirit of the holiday season by donating a toy, as well – and showing their children that they can make a difference in the lives of other kids who may not be as fortunate as they are.

Since that first Winter Wonderland fundraiser in 2017, tens of thousands of dollars have been raised for Christmas in the City.


Monday Mania

Nobody wants to disappoint kids who’ve already had plenty of disappointment in their lives. So, beginning in early December, Christmas in the City registers families with a demonstrated need and assign them a time to go shopping. At Monday Mania, they stock their shelves with new toys, sports equipment, books, clothing and other goodies – all donated thanks to the generosity of their supporters – and have families fill their shopping bags (for free, of course). They even make sure there are gift cards for the older kids who’ve outgrown dolls and trucks.

Each year at Monday Mania, CITC distributes upwards of 25,000 items to deserving families. And they even make sure they get plenty of wrapping paper.


Sad news for all friends of Christmas in the City family. In October of 2020, Jake Kennedy died. The world is a lesser place without Jake in it – less kind, less joyful – but it’s a more magnificent place because we had this good and great man among us for 65 years. His legacy lives on through his wonderful family, and through Christmas in the City.
Jake Kennedy and his wife, Sparky, are holding a gift wrapped in red wrapping paper with green dots. Sparjy is wearing a gray top and a Christmas tree headband and Jake is wearing a white dress shirt.m

(Photo courtesy of Christmas in the City)


Toy Pickup Generously Donated By

98.5 The Sports Hub is a proud partner of Christmas in the City