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Royalty in Roxbury: Community celebrates little girls of color on Princess Day

Valerie Stephens, center, organizer of Princess Day, poses for a photo with attendees at the 10th Annual Princess Day on Saturday.Erin Clark / Globe Staff

Roxbury was replete with royalty Saturday as dozens of pint-sized princesses descended on a local playground to celebrate themselves as girls of color on Princess Day.

Hundreds of families with daughters dressed as princesses filled the Gertrude Howes Playground to participate in an afternoon of activities like decorating crowns and bongo dancing.

“Princess Day is a day that we take time out to celebrate little girls of color,” said organizer Makeysha Montgomery, 38. “It’s a day that they learn about culture and creativity.”

The event, also about “entertainment and exposure” to the arts, featured an array of performances, including classical cello and bongo drums, she said.


Valerie Stephens — an artist, performer, and storyteller — conceived of Princess Day almost a decade ago as a party for her 5-year-old grand-niece and her friends.

Since then, Princess Day has grown to host hundreds of girls. But the core concept hasn’t changed: It’s all about “little girls of color having fun,” said Stephens. “It’s about celebrating who you are around others who are like you.”

Tessa Carless, 3, checked out the colorful feather boas in the photo booth.Erin Clark / Globe Staff

At 15, Jade Jackson, the grand-niece who first inspired the event, is still participating in Princess Day — now as a volunteer.

“It’s such a good feeling to be able to inspire all these young girls,” she said.

Throughout the afternoon, there was an array of activities for the little girls in gowns — decorating sashes, coloring crowns, taking photos, reading books, watching performances, and receiving face paint.

Charmaine Santiago Galdon taught princesses how to Bongo Dance.Erin Clark / Globe Staff

Among the performers was Lily Li-Nagy, 7, who recited a poem she wrote called “The Shape of Love, Peace, and Unity,” which opened with the lines, “Love doesn’t have a shape. She follows her own direction.”

The girls were given supplies, snacks, and dolls. Organizers also raffled off prizes, including backpacks and over a hundred tickets to Broadway in Boston’s “Anastasia.”


All the items and the funds for Princess Day are donated, and it’s important to Stephens that everything at the event is free.

“I grew up very poor, and I don’t want any mother or father or family member to say, ‘No, baby, we can’t get that for you,’” she said.

Aja Ramsey helped her daughter, Telynn, put on her crown.Erin Clark / Globe Staff

Despite a decade of dedication to Princess Day, Stephens almost canceled this year’s celebration.

“I wasn’t going to do it this year,” she said. “To be quite truthful, I have to move — I’m being priced out of the area. They’re raising my rent and I can’t afford it.”

Stephens changed her mind after she received e-mails, texts, and calls from the community asking her to hold the event and reminding her of its importance.

“There’s so much around us that makes us think that we are not enough, that we are inadequate, that we are ugly,” she said. “Little girls need to know they’re special.”

Valerie Stephens, organizer of Princess Day, welcomed attendees to the 10th Annual Princess Day at the Gertrude House Playground.Erin Clark / Globe Staff

Parents who brought princesses to the event said they hoped their daughters were empowered and inspired.

“I wanted to make sure that she knows, no matter where she goes, that she is a princess, aspiring to be a queen,” said Van Nessa Jemmott, 67, of her 8-year-old daughter, Rebekkah.

For Jemmott, who lives outside Worcester, it was “uplifting and it’s refreshing” to be surrounded by families from the communities of color in Boston.

“It’s just what is necessary before these girls go back to school,” she said. “Some of us live in places where the only chocolate faces are the ones we see at home.”


Vivian Showell came to Princess Day with her daughter Aryella, 8, whose dress was pink and puffy — just like her preferred princess, Sleeping Beauty.

“It shows all the Black and brown girls around Boston that they are special, and they are princesses, and they are queens,” said Showell.

Artis Ramsey blows bubbles at Princess Day.Erin Clark / Globe Staff

Jisca Philippe, of Roxbury, has brought her daughters, aged 5 and 6, to Princess Day for the past three years since “it gives them the opportunity to just be girls and live in the moment.”

For Philippe, there’s also a special significance to the fact that Princess Day is in Roxbury.

“A lot of times when we hear about Roxbury or certain communities, it’s always crazy news, or discouraging,” she said. “These spaces where our generation feels celebrated and feels loved and gets affirmation are so important.”

Sophia Vargas, 6, said she enjoyed the event.

“I think it’s fun seeing all the princesses,” she said. Though she loves princesses — especially Jasmine — she said she wants to be a doctor when she grows up.

Cousins Ava Salcedo, 7, left, and Sophia Vargas, 6, picked out stickers and jewels for their princess sashes at Princess Day.Erin Clark / Globe Staff

Princess Day also allows adults to celebrate the diversity among princesses that wasn’t there when they were children.

As a child, “nobody ever called me a princess,” said Stephens. Princesses of color “didn’t exist — not in toys, books, or anything. We never thought of ourselves as princesses.”

For Montgomery, who wore a neon tutu and a jeweled tiara, Princess Day is “a chance to relive childhood” while inspiring the girls of generations to come.


“We want them to know that every day in life, they are a princess,” said Montgomery. “We want to drive that self-esteem into them, that they are special just the way they are.”

Makeysha Montgomery, 38, danced with 2-year-old Nova Mason, who was dressed as Princess Belle.Erin Clark / Globe Staff

Camille Caldera was a Globe intern in 2022.Follow her on Twitter @camille_caldera.