If you’re launching a new art fair, Helen Toomer is your woman. Crackling with warmth and seemingly boundless energy, the U.K. native is about as gregarious a leader as any such enterprise could hope for, the polar opposite of arty hauteur. Toomer got her start, fresh out of college nearly 20 years ago, at Ramsay Fairs, the company that runs Volta and the Affordable Art Fair. Now, on the heels of the successful fourth edition of Upstate Art Weekend, which she founded in 2019, Toomer is prepping to direct the inaugural edition of Photofairs New York, a new photo-based contemporary art fair that will make its debut at Javits Center this September.

Toomer’s new position marks the fourth job she’s held with an art fair over the years. She was the founding director of New York’s Collective Design Fair, spent several years running Ramsay’s Pulse Contemporary Art Fairs in New York and Miami Beach, and most recently did a yearlong stint at the head of the IFPDA Fine Art Print Fair, also in New York.

Meanwhile, Upstate Art Weekend, which celebrates the cultural vibrancy of the Hudson Valley, has grown to include over 100 museums, galleries, and other arts organizations across 10 counties.

At the heart of the festival is Stoneleaf Retreat, the artist residency she founded in 2017 with her husband, Eric Romano—an art-fair veteran himself who runs Space Design and Production, which stages events like the Untitled Art Fair in Miami Beach—at their home in Eddyville, New York. Stoneleaf is dedicated to supporting women artists, a longtime passion for Toomer, who also runs Art Mamas Alliance, a support group for mothers in the art world she founded with Whitewall editor-in-chief Katy Donoghue in 2019.

Ahead of Photofairs’ New York debut, we spoke with Toomer about what to expect from her newest venture, the importance of building community in the art world, and how she manages to wear so many hats while raising Harry, her soon-to-be five-year-old son.

Murals by Lizania Cruz and Macon Reed at Stoneleaf Retreat. Courtesy of Helen Toomer.

What first got you interested in visual art?

My mom remembers that I would always hold up my fingers to make a frame, and say, “That would make a good picture.” I always saw things differently than the rest of my family. Then, when I was 14 or 15 years old,  I saw Francis Bacon’s Three Studies for Figures at the Base of the Crucifixion. It just stopped me in my tracks. I felt all the pain from that incredible triptych, and I just felt overcome with emotion. I was like, “I would love to be able to do that.”

I went to art school at the Arts Institute of Bournemouth and I tried to be an artist—but an artist, I am not! But I realized I really enjoyed putting together our end-of-year show in London. It was great to work with my fellow students in figuring out the logistics, curating it, promoting it, and arranging free beer. Something clicked that I got more satisfaction out of organizing than creating as an artist.

You got your start with Ramsay Fairs back in 2004—what drew you to art fairs?

You essentially build a little city in a short amount of time, and it brings a global-focused community together. I’ve always been fascinated by the physicality of it, the production and the layout and the setup—and when the artwork comes in, it’s incredible. You get all the different personalities of the galleries and the artists and the visitors.

Stoneleaf resident Tamar Ettun with her child during Upstate Art Weekend.

I get the sense that your favorite part about fairs is working with the artists themselves. Is that why you and Eric decided to start an artist residency at your home when you moved upstate? 

I just get so excited to be with artists and get insight into their practices—these windows and glimmers they give to us are incredible. To me, artists are truth-tellers. That sounds incredibly cliché, but I believe in the power of what they do.

When we started the residency, our realization was that Stoneleaf was the gift of time and space for artists. Becoming part of their journey and offering continuing support has been incredible. Tamar Ettun, for instance, was part of a wonderful group residency in 2019, and then she came back in 2022 for a family residency. Same with Liz Collins and Rebecca Reeve. Rebecca told me she was actually pregnant when she did her first residency, and then she came back with her child. I love that Stoneleaf can become a continued home if the artists need or want it to be,

Why did you decide to focus on women artists at Stoneleaf? When did you realize that you wanted to provide opportunities for women with children, specifically? 

Coming from an art-market perspective where women are marginalized, I wanted to be able to support them further. My friend Michi Jigarjian—president of the Baxter Street at the Camera Club and curator of the Rockaway Hotel—once said to me, “When you’re feeling overwhelmed about everything that can or cannot be done, think about your corner and what you change in your corner.” For me, that was Stoneleaf.

When I had my son, Harry, in 2018, it was honestly quite a shock to the system. Pre-child, Eric and I were always fighting for the elusive balance. Now I look back and I’m like, Oh, we had so much time then! And now the balance is an illusion.

I realized artist mothers often don’t have the time—or they don’t want to be or cannot be away from their families. So that’s when we decided to open Stoneleaf up to family residencies. And I love that it’s a safe space for families and kids.

How great is the demand for these residency slots? What do you see as the challenges of being a mother in the arts? 

We did applications for an Art Mamas residency, with three slots for a one-week group residency, followed by a one-week family residency for one artist. We had 300 or 400 applications for those four spots, and reading through all the applications was just heartbreaking. The need for artists to have the space to either continue or get back to their practice after having kids is phenomenal. Their time is spent keeping the littles alive, and then keeping the house clean, and then doing their job, and then cooking dinner—and all of a sudden all the hours are gone.

I wish that before I had Harry, people had been transparent with me about what it is to be a parent. You prepare, obviously, but you can’t know what it will be like. It’s brilliant and brutal all at the same time. I had spent my entire life trying not to get pregnant. And then when Eric and I got married, we decided we wanted to have a baby and it took nearly three years. That was really tough. I couldn’t talk to many people about it.

Then after Harry was born, I really struggled. I had an emergency C-section and I wasn’t able to breastfeed. I felt like I failed. But I finally realized I had to be happy and healthy, because my happiness and my health fully impacted Harry. You feel so alone, but there are so many people going through similar things, and if we can help one another, that’s the most important thing. This is one way that Katy Donahue and I really connected.

She had her son six months after I did. I remember seeing Katy post something on Instagram about breastfeeding. I just messaged her to say, “Whatever you’re doing to be happy and healthy is going to make your baby happy and healthy.” And we started talking and being open and honest and it went from there.

Open Studios Event at Stonelead Retreat during Upstate Art Weekend. Left to right: Maya Evans, Tiana Webb Evans, Lora Appleton, Helen Toomer, Marina Garcia-Vasquez, Rebecca Pauline Jampol, Hayley Carloni. Courtesy of Helen Toomer.

Leaving Brooklyn for the Hudson Valley, what were your expectations about the art scene there and how did they line up with reality? How has running Upstate Art Weekend expanded your art horizons? 

I absolutely love being upstate. I think it’s incredible what creativity is up there and has been up there for years. We bought our place in 2016 and started the residency in 2017. And then Harry was born up there in 2018. Before the pandemic, we had decided that we were going to relocate up there full-time. Obviously, the pandemic expedited that process.

Starting Upstate Art Weekend in August 2020 was a response to being isolated and realizing that we have this gift of space. Bringing people together outside, safely seeing each other and seeing art again was incredible. And there are so many people and organizations who were already up there and had been doing great work for years. There are the big names that we know, like Dia: Beacon, Storm King, Olana, and Art Omi, and then also some amazing galleries have been bringing their program there and producing incredible shows, like Alexander Gray, September, and Elijah Wheat. So it’s super vibrant.

Going into our fifth year now is a chance to reevaluate this little project that I made up, thinking about what it is and who it serves. We may need to divide it up, expand it, or do it multiple times. This year has been so crazy busy with all the projects that I’m running that after this fair, I’m looking forward to going inward a bit, refocusing, and being able to take the time to move forward.

Helen Toomer and Scott Gray, CEO of Photofairs. Photograph by Casey Kelbaugh.

Thinking about your new position with Photofairs, what drew you back into the fair world after focusing on Stoneleaf, Upstate Art Weekend, and Art Mamas in recent years?  

I thought I had hung my art-fair hat up! And then I got an email from a friend asking if I would talk with somebody about Photofairs launching a new fair in New York. I always take these kinds of calls, because I can help point people in the right direction.

But when I spoke to Scott Gray, CEO of Photofairs, I liked the way that he spoke about what they wanted to create. I liked that it was at the Javits Center at the same time as the Armory Show. And I love this niche of photography—it has always been an innovative medium, and it’s just so vast in terms of the tools that can and have and will be used. I wasn’t expecting it, but I got off the phone, and my wheels started turning. I thought, “I’m excited to do this!”

I cannot wait for people to come and experience everything we’ve been planning, to walk through and discover some incredible artists and galleries that they may not be connected with yet. Because that’s what I love—the connections. And I think that’s why I always come back to art fairs, because it’s having those connections in real life. It’s having conversations and taking in what we’re all there for, which is ultimately to support artists.

Do you see any specific challenges trying to break into the New York fair market, especially as a dedicated contemporary photo image fair? Why do you think the fair—which started with Photofairs Shanghai in 2014—will succeed in New York in a way that it didn’t in San Francisco, where it held two editions between 2017 and ’19? 

This is the first fair that I’ve worked on that has had a strong international foundation, and that comes with a wealth of knowledge. San Francisco and the West Coast has always been incredibly tricky market. In New York, we know the market here, we know it’s focused, we know it’s concentrated. San Francisco was a great idea to start with, but it didn’t make sense in terms of continuing.

Photofairs has been thinking about launching in New York for years, and they’re very committed to being here for the foreseeable future. I’m excited about the first edition, but I also see it as seed planting, and I’m excited to see how these seeds are going to grow and how these flowers are going to blossom over the years.

What do you think has changed the most about the art-fair landscape since you stepped away from Pulse in 2017, and what lessons from your time there are guiding you in your new role at Photofairs? 

There’s nothing like seeing art in person. I think that art fairs contribute to sales and to the ecosystem for sustainability for galleries and artists. It’s a convening for writers, collectors, and curators, all to come together and celebrate the art that has been made. So the model has been pretty solid throughout the years: pick a great location, make a great floor plan with incredible galleries and artists, and then make sure you’ve invited the right people. That hasn’t changed.

I think people were getting fair fatigue before the pandemic, but after people wanted to get together because we were restricted for so long. It’s more of a celebratory affair than maybe it was before. I also think that people might be picking and choosing a little bit more about where they go, as opposed to running around all the art fairs on the global circuit. But with Photofairs being at the same time as the Armory Show, it feels like kicking off this back-to-school season in New York. I think it’s a win-win.

Elliot and Erick Jiménez, The Grand Odalisque (2022). Courtesy of Spinello Projects, Miami.

How do you manage to juggle all your various hats? What does a typical work day (or week) look like for you at the moment? 

The answer is just I just do. I wish I had a magical pearl of wisdom, like “Get up at 4 a.m. and meditate.” But that’s not me. It’s eight iced coffees, a lot of lists, and being on my computer all the time.

This year has been particularly busy, but being at Stoneleaf and being able to work remotely has been great. I can look out and see green. Harry can come home and play after school. But there’s also our proximity to New York City. I’ve been going back and forth a lot, and I love coming in and running around and seeing shows and friends and absorbing the energy.

I’ve been traveling so much that there isn’t a typical day. The only steady things in my daily life are iced coffee, kisses from Harry and Eric, emails, and Instagram.

You have a bit of a reputation as an “art whisperer” for nurturing art and artists in a way that feels really independent from the pressures of the market, which is kind of remarkable considering how much work you’ve done with commercial fairs. How do you square the two?

I am definitely going to add “art whisperer” to my LinkedIn—I love that. it just comes back to loving artists and loving people and listening. Stoneleaf has been a super big part of that. And artists will come to Stoneleaf and say, “This gallery has asked me to be in this group show, but I’ve never done a consignment form,” or “I want to apply to this residency or this job. Can you be a reference?” and I’m like, “Of course.”

I feel fortunate that I am able to be part of their journey. There is no fluff or pretense about me—other than my ridiculous outfits. Being able to have honest conversations and have an exchange of vulnerability has led me to have incredible relationships with artists. I always wish that I could help more because they need nurturing.

I hope that we can always be a resource or a friendly hug for the artists who are part of the Stoneleaf family. And I think that art fairs are part of that community building. They are great for providing a snapshot of the market. Yes, art fairs are part of the market—and rightly so. We want the galleries to make money; we want the artists to make money. But I’m interested in how they build community and support the art ecosystem and the programming is super important to that.

At Photofairs New York, we will have talks every day. There are lots of opinions about photography, digital art, new media, A.I., and we’re bringing all these these different opinions together under one roof. It will be an annual convening with this exchange of information.

Photofairs New York takes place at the Javits Center, 655 West 34th Street, New York, New York, September 7–10, 2023.