The most wonderful time of the year? For Wanda Whiteside, it was always February.

Whiteside, the artistic director of Live Garra Theatre in Silver Spring, grew up in a less-than-diverse community on Long Island, and February meant she would get packages from her grand-aunt and grandmother in Columbia, South Carolina.

“They would send me these head shots of George Washington Carver and Harriet Tubman and Harriet Beecher Stowe, with a little blurb about who these people were,” she recalled. “And I would go to the principal and say, ‘OK, it’s Black History Week — we have to put these in the front trophy case.’ It was something I would do every year.”

Whiteside, who trained at the Boston Conservatory of Music, HB Actor’s Studio and Usdan Center for the Creative and Performing Arts in New York, is now a longtime Maryland resident. She stayed in the D.C. area after earning a bachelor of fine arts degree in theatre arts and a master of science in business management from Howard University — she will complete a Doctor of Education in organizational leadership soon — and has never stopped telling the stories of her people. In the run-up to Live Garra Theatre’s holiday production of “Almost There: Songs of the Season,” she is happy to explain why.

“We, as a people, have a story to tell,” she said. “It can’t be told from the point of view of others, which sometimes happens — it happens with all cultures, I think.

“I want the company to speak to the story of the African American heritage and, with culturally-specific theater, bring all cultures together.”

Cultures, yes, and people, too, especially at the end of December when Christmas cheer is in the air, the principles of Kwanzaa — unity, self-determination, collective work and responsibility, collective economics, purpose, creativity and faith — are at the fore and the possibilities of a brand-new year lay ahead. “Almost There: Songs of the Season” celebrates it all, with two original plays and a jazz band ready to perform at Silver Spring’s Black Box Theatre.

“These two pieces, two short one-acts, are uplifting,” Whiteside said. “I wanted to do something fun, to incorporate music and to close the year out on an upbeat, positive note.”

To do that, she is staging Thomas Mason, Jr.’s “No One Hears the Night — A Modern Jazz Tale,” and once again, has called upon playwright Joy Hunter Carroll, a native Washingtonian and fellow Howard University alumna whose play “Grandma’s Christmas” explores family dynamics at the holiday season.

The playwright has a bachelor of arts in communications from Howard University’s School of Radio, TV and Film. Technical writing, she said, “pays the bills, but there’s something about playwriting. I like the live audience, the immediate feedback.” She also likes the idea of creating a family-friendly event and showcasing contemporary issues that families in the audience can relate to.

“When the economy is like this, a lot of kids, not teenagers — adult children — are moving back home,” Carroll pointed out. “Seeing how families deal with that, talking to some mothers, I thought it was an interesting idea.”

It is not the usual holiday tale, but it is one that tells a story of a family celebrating Christmas in its own evolving way. “It’s not a traditional Christmas play, and that’s one theme it kind of explores: tradition,” Carroll said. “We do the same thing every year; we can’t change anything just because we’ve done it for so long.

“But there’s always room for new traditions; there’s always room for new experiences, especially if they help us to grow, to be better, to create wonderful memories for people that we love and for ourselves.”

Whiteside thinks that memories will be made at this year’s Live Garra holiday performance. This year, in addition to directing, Whiteside will be polishing her performing chops in the role of Grandma in “Grandma’s Christmas.”

“I’m an actor,” she explained. “I do sometimes have to step in and perform if I need to.” She noted that while “Grandma’s Christmas” offers Hawaiian flavor and fun, “No One Hears the Night,” about a jazz legend searching for his legacy, brings the music, especially with the group Musik Konnekt in the house, and a few surprises sprinkled through each show.

“Grandma’s Christmas,” Whiteside said, “is kind of a coming of age story: the mom — the grandma — is coming of age and starting to feel like it’s time for her to make her life and do things for herself. And her daughter has to face reality: she’s a grown woman and she has to stop depending on her mother for everything and start doing things herself for her kids.”

The characters are African American, yes, but “the themes are universal,” Whiteside said. “The soul has no color. The soul is the soul. We’re all the same.”

Especially mothers and daughters. Whiteside’s mother, the granddaughter of a slave, passed away 10 years ago on Christmas Eve. Whiteside and her husband Arthur Seaman had owned and operated the Bonifant Theatre Space in Silver Spring before deciding to open a new company — and Whiteside whispered a prayer to her mom when she was considering whether or not to move forward.

“She’s actually the reason Live Garra came to be,” said the director. “We were moving out of our Bonifant Theatre space. It was her birthday and I just kind of said, ‘Oh, mom, does this mean we should just give up?’”

The answer came in the form of an inspirational quote from a book that Whiteside reads daily. On Sept. 25, her mom’s birthday, the book said, “’The Brazilians have a phrase for people who never give up,’” she recalled. “’It’s called Garra: to hold on, to persevere and to go the distance.’” She saw it as a sign: to “live garra” meant to never give up on a dream.

“‘Live’ speaks to the voice in the community that sometimes is not heard,” Whiteside added. “The word ‘garra’ means persevere. It’s Portuguese and it means, literally, to hold on and never give up. That’s the soul and the spirit of the African American heritage.”

The heritage of her mother, her minister grandmother and great-aunt, her great grandmother who was a slave. Live Garra is the way Whiteside tells their story and the stories of those who came before. “There were days when my ancestors were hiding in the water so that the dogs couldn’t smell their scent,” she said. “Which is where that Negro spiritual song came from: ‘Wading in the water, wading in the water, children …’”

She sang it softly, the voice of her enslaved ancestors telling the story of how they would wade in the water to stay alive.

“Then they could go on,” she said. “Go north to freedom, following the Big Dipper — the Drinking Gourd.” She paused, as if the weight of history was upon her.

“It’s always been inside me,” she said. “Like a fire that burns, saying, ‘You have to continue to tell this story.’

“That’s why I do it.”

Live Garra Theatre presents “Almost There: Songs of the Season,” at Silver Spring Black Box Theatre, 8641 Colesville Road, Silver Spring. Performances start at 8 p.m. Thursdays, Dec. 20 and 27; Fridays, Dec. 21 and 28; Saturdays, Dec. 22 and 29; and at 3 p.m. Sundays, Dec. 23 and 30. Tickets are $25 online, $30 at the door and $20 for seniors. For tickets, visit www.brownpapertickets.com. For information, Call 855-575-4834 or visit livegarratheatre.org.