Kym Chambers built her vintage business in the hallway of her Brooklyn walk-up with what she called “one rack of clothing and Shopify and a dream.”

For the past two years, Chambers has occupied a storefront on Main Street in Saugerties, where the Toronto-born curator showcases BIPOC women, sustainable brands, vintage, and queer Hudson Valley artists.

On Feb. 26, Chambers hosted a conversation with the observational painter Jordan Casteel and writer and educator Nina Tucker. Casteel, a MacArthur Fellow—a recipient of the foundation’s “genius grant,” which provides unrestricted support to artists and thinkers—was on tour for a new Phaidon monograph, an in-depth book surveying a single artist’s life and work.

Casteel is known for large-scale portraits of people of color—friends, neighbors, students and community members rendered in luminous color and steady, unflinching eye contact. Her paintings turn everyday encounters into a kind of insistence, that the people who animate a place should be seen, and seen fully.

The evening also spotlighted Upstate Color—known colloquially as UPCO—a WhatsApp-based collective co-run by Tucker and Casteel that has become a gathering point for BIPOC residents across the region.

Chambers, 44, who has more than 25 years of experience in fashion and retail across New York, London and Toronto, moved to Saugerties four years ago.

“We were like, this is not sustainable. We need more space,” she said about living in New York City. “We moved here not knowing anybody.”

That search for community, and the question of what it means to be visible in a place, became personal when Casteel met Chambers and her husband, Deon Hamer, 55, who moved upstate four years ago with their young son, Noah. Casteel relocated to the area during the pandemic in search of more space and connection.

Community deepened into collaboration through grief. Chambers and Hamer lost their second child. On July 15—the one-year anniversary of that loss—Casteel photographed the family in their garden, which they had waited several seasons to see in full bloom.

The resulting 94-by-80-inch oil painting, “Naima’s Gift (Deon, Kym, and Noah),” completed in 2023, became both portrait and memorial.

“The day I spent with Deon, Kym and Noah will forever be ingrained in my heart,” Casteel wrote of the sitting. “The sun was out and they had waited several seasons for this moment—when their garden would be in full bloom.”

She described the painting as the beginning of a body of work “reckoning with my own dedication to the notion of seeding, using the garden to process my own journey.”

“Its bloom honors the cyclical nature of life, perennially flourishing and impermanent,” she wrote.

Casteel said living in the Hudson Valley provided space, but not simplicity.

“There’s such nuances in the Hudson Valley. And learning the blocks like block by block, where your safety lies and doesn’t lie,” she said. “The community that we’ve built is like my bank, but what does it mean to be, in a rural space as a person of color is also the river that I’m constantly trying to navigate.”

She said the choice to name the painting after the child they lost, Naima, was a collective decision.

“I thought it would be poignant to choose the name of the child that we lost. So that’s why the painting has the name that it has,” Chambers said.

Growing up, Chambers did not feel very newsworthy or very particularly beautiful. Seeing herself on the canvas was disorienting and affirming.

“I was so completely at a loss for words,” Chambers said. “To see myself represented as a whole figure, I was like, ‘Is that me? It was incredibly empowering and powerful.”

The third voice in the conversation was Tucker, 29, an educator, writer and community organizer who co-runs Upstate Color with Casteel. The group began in 2021 as a Discord chat before moving to WhatsApp, where it now includes more than 600 members.

Upstate Color organizes gatherings across the region, often in collaboration with other local ventures, including Kite’s Nest, African Roots Center, and Enoki, as well as Big Towel, a Hudson-based mobile sauna project founded by Kelly Crimmins that operated in Germantown and now Kingston.

”UPCO and Big Towel have collaborated on sauna events. I am trying to democratize sauna as a way to allow all people to self realize. Leisure shouldn’t be elite,” Crimmins said.

For Tucker, the work was personal as well as logistical.

“It’s an honor to sit with such brilliant women who are creating space tangibly,” she said.

Her worldview anchored the group’s ethos.

“I’m very much someone who believes in the universality of the human experience,” she said.

At Chambers Vintage, that universality translated into atmosphere.

“I just want people to feel welcome and joyful,” Chambers said.

What unfolded Feb. 26 was less a formal panel than what Tucker described as “casual” and “very real”—a conversation shaped by migration, memory and mutual recognition.

For Casteel, the Hudson Valley was no longer an escape from the city. It is home and part of the work—landscape as integral to collaboration and community as subject and source.

“It’s about the things that I see and the people that I see and how they all kind of intertwine,” she said.

Noah Eckstein is the editor-in-chief of The Overlook. Send correspondence to noah@theoverlooknews.com.