Sara Macaulay Celebrates 40 Years at Winsor

Each winter, the Winsor Board of Trustees hosts a seated dinner for the faculty and staff to celebrate major milestones and to honor their Winsor tenure. At the annual Faculty, Staff, and Trustee Dinner on Tuesday, December 5, 2023, Visual Arts Department Head and Eleanor Thomas Nelson ’49 Chair in Fine Arts Sara Macaulay celebrated 40 years of service to the school. 

Ms. Pelmas’s remarks are excerpted below:

It is, admittedly, a daunting task to talk about Sara Macaulay and her 40 years of service to this school! What a resume she has at this point, and how completely appropriate that the resume is in one sense the least of her accomplishments—and I think she would be the first to say this. But let’s start there anyway. Sara came to Winsor in the fall of 1984, as Sara Grove, just after earning her master’s degree in teaching from RISD. Over the four decades since, she has held what may be a record number of positions at Winsor. And she got married and had two children. She has served as department head—twice. She was a class coordinator before they were called class coordinators. She was an admissions interviewer and the Banner advisor. She has taught at every grade level, and every course the Visual Arts Department offers, with the exception of darkroom photography and ceramics. She has also taught Technical Theater and Scene Painting. She brought the AP Studio Art course to Winsor. Together with former English teacher and Families Relations Coordinator Lynn Randall, Sara helped develop the ILE. Even before Winsor had created our global programs, Sara developed and taught lessons that embraced the art of cultures around the world and through the ages. Her assignments have included making Japanese tea bowls, Anasazi wall paintings, block prints of African myths, and Islamic tiles. She has cataloged the entirety of Winsor’s art collection, has helped students curate shows based on our art, has built our collection through strategic acquisitions that broaden the examples and inspiration for our students, has helped to share these shows with the larger community, and has brought us art from former teachers Joanna Kao and Adrienne Robinson. She helped us get the Cecilia Beaux painting of Mary Winsor to the MFA when it needed restoring, and was part of the group who went to pick her up and get a back-stage tour of the MFA and its restoration practices. She teaches online classes with One Schoolhouse, which made her the natural person to help Winsor transition to the online world we lived in during the pandemic. 

And she has taken Winsor students all over the world: to Spain, Turkey, Italy, and one that visited Prague, Vienna and Budapest. For 25 years, she designed and created the sets for our annual Shakespeare play, and one year, she even traveled to England with the director of the Shakespeare play to research the Bard and the Globe Theater, then returned to recreate the famous theater at Winsor for that year’s Class IV play. When the Visual and Performing Arts Departments were one department, Sara was the utility player—doing everything, enjoying it all, and bringing so much life and art to the school.

In 2020, over zoom, she was awarded the Eleanor Thomas Nelson ’49 Chair in Fine Arts, which she currently holds, and which was held only by one person previously—Choral Director Lisa Taillacq. Sara is a master teacher, certainly, and she also knows so many practicing artists that she can bring a steady stream of guest artists to the third floor to work with her students. She has brought in the work of local artists, like Kitty Wales’ shark and sturgeon hanging in the LOC, alumnae Meghan Weeks ’04’s paintings, and the collection of prints and paintings in the art department itself. She has traveled across the country and around the world to study with artists and keep improving her own craft. 

She has joined in the faculty/staff talent shows and has actual talent in dancing and acting; and she has been an avid horseback rider since the age of 12, more recently competing in dressage and the quadrille—which is a team of horses doing a choreographed ride to music. As Sara says, “it’s like dancing with your horse and a bunch of your friends with their horses.”

Those of you who have been fortunate enough to work closely with Sara have seen firsthand her commitment to her work and our students. Former colleague and department head Julia Harrison says: “Sara thinks about how to broaden student exposure, understanding, and enjoyment of the arts all the time—gaining new ideas for the actual making of it in projects and processes through the work of past and contemporary artists, planning local and international student arts trips, and adding and refining course options. Her mind holds a wealth of arts teaching information, a comprehensive art catalog if you will, that she can and does readily access and share with students and colleagues, and this, along with her ability to guide students in their growth and development as artists, is what makes her an incredibly gifted and effective art teacher. Forty years in, Sara still finds the act of teaching (and designing the most compelling and up-to-date secondary school visual arts program) to be the best job anyone could have!” 

Everyone who has had the chance to work with her in the art department calls her unflappable, curious, wise, and surprising! Current colleague Mia Tinkjian jokes: “You know how artists are: moody, unreliable, disorganized, scattered and oftentimes messy. And yet one of the most talented art teachers I have ever met is none of these things. Sara Macaulay is creative, thoughtful, generous, organized, meticulous, and very neat. She is also full of surprises. I never assume that I know exactly how Sara will respond to a question or situation. I only know that I CAN assume she is ten steps ahead of me in her thought process, and that she is leading from a place of wisdom, fairness, kindness and support.” To which Emily Valenza adds, “Sara Macaulay is a wonder, and sometimes a bit of a mystery. She is as much a wise mentor who knows everything about everything as she is an artist with a beginner’s mindset who is curious enough to try any new idea. Sara can shift from a serious student critique to a ridiculous spirit week costume brainstorm without batting an eye.”

And Sara not only loves her job, she also clearly loves her students. Recent alum Audrey Cheng ’23 calls Sara “one of the most influential people’” in her life. Audrey continues, “Ms. Macaulay teaches with such love and care for her students, as well as such authentic enthusiasm for art. She is constantly thinking about her students’ artwork and will come up with fantastic ideas for them at any hour of the day. I received many emails from Ms. Macaulay that started with ‘I had an idea while driving into school this morning for you’ and ended with ‘I cannot believe how much you have grown! …She works tirelessly to ensure that Winsor is a place where students can create and know that their work is worth something.” 

Many alums feel exactly that way. According to Kaylee Chang ’19, “[Ms. Macaulay’s] belief in her students and willingness to see our promise, when we often weren’t able to fully recognize it, was beyond meaningful to me.” Anissa Patel ’23 notes that “she is not only a fantastic teacher, but also a truly kind and genuine person who cares to the fullest degree about every aspect of her students’ and advisees’ lives, whether that be academic, extracurricular, or personal. Her time at Winsor and the fact that she’s worked in many different capacities here gives her an incredibly unique perspective which I am so grateful to have experienced.” And Michelle Pu ’20 shares her belief that, “Ms. Macaulay saw something in me as an inexperienced art student that I did not realize myself. Through her kindness, warmth, and deep knowledge of art, I was able to find my own artistic path.”

Alum Petra Sarkisian ’23 identifies the third floor art studio as the very best place on campus, hands down. Petra recalls, “Art class with Ms. Macaulay was truly a highlight of my high school experience. Even now, in my college painting classes I can hear her voice guiding me through the process of each painting, both in my head and in real life, always excited to hear about my latest art endeavors even though I’m no longer her student. I know that I will incorporate her teachings into both my mindset and my skills for as long as I am making art and I feel exceedingly grateful to have been taught by her.” And alumna Meredith Gamer ’99, now herself an art history professor at Columbia, wrote saying how important it was for her—among other things—that Sara was a working mother, and what an extraordinary example that set. Sara herself says, “Sometimes you don’t know exactly what they are learning from you.”

Even at moments when Sara might very much want to aim a student in a particular direction, she allows them to find their way. As professional painter and Winsor alum Meghan Weeks ’04 puts it, “[she] offer[ed] expert guidance where we needed it, but never in a way that felt like we couldn’t pursue our own visions with the range of materials that she made available.” Meg goes on to describe the challenge of developing her AP portfolio: “I wanted to paint something on a large scale, and Ms. Macaulay patiently walked me through the process of fitting together stretcher bars, affixing a behemoth sheet of cotton, and applying layers of gesso to create an intimidatingly large canvas. I can’t recall why, but I opted to use that pristine surface to paint two highly-rendered, hideous llamas, both of which looked like they were on the verge of spitting—as I imagine any reasonable critic looking at this strange painting would. The piece found its way into a pile in my parents’ basement and thankfully not into my AP portfolio, but at no point do I remember Ms. Macaulay making that call for me. Rather, she always empowered us students with the confidence to express ourselves creatively and to make our own (often necessary) edits, bolstered by the sense that she was always there to guide us when needed. ”

And that guidance paid off for her students. Former department chair Sharon Gorberg described how “Sara enables the girls to feel confident about their abilities as artists,” and noted the many National Scholastic Art Awards her students have earned under her direction. In fact, Sara has six national medals (three gold and three silver) hanging over her desk, each one representing a student who earned a national medal in the Scholastic Art Awards. One of those medals represents Franchesca Vilmenay ’22, who earned a national gold medal for her portfolio. She was one of only 22 students to be recognized that year from a field of thousands of students. Sara describes Franchesca’s win as “a once in a lifetime experience for a teacher,” and shared how honored she was to have had the experience with Franchesca.  

But it’s not the award winners that are a true measure of a teacher. It’s the students whose lives are changed because they learned a new way to express themselves, who approach beauty differently now, whose creativity has grown, whose worlds are different because of the art they have created and the art they have been exposed to. And, honestly, spending a few hours in that gorgeous third-floor art studio would be enough to transform anyone for life. 

So it’s not surprising that, when we asked Sara about her career highlights, she didn’t point to medals or awards, but said, “When I think about the highlights, it’s not particular achievements per se, it’s more about the people that I’ve had the immense good fortune to work with throughout the years.” But she did also identify a few highlights: “to see students I have worked with and mentored graduate and go on to art school. When I first came to Winsor, that never happened. Being able to teach on a daily basis in the beautifully renovated art studios. Being able to teach full credit art classes. These may sound so mundane but they are definitely highlights (on a daily basis) for me, and they make it a pleasure to come to school every day.” 

I know I’m not alone tonight in feeling enormously lucky to work with such an accomplished, dedicated educator, colleague, and artist. Over the years, many of our new teachers have had Sara as a mentor when they start their Winsor journey. Mark Brooks Hedstrom and Lisa Stringfellow were two such teachers. Lisa remembers how “Sara shared her experience and time generously and reassured me that I would make it through my first year. She saw her relationship with me as more than just a school-assigned role, but as a friendship, one that we have maintained years later.” And Mark notes, “She was very helpful in helping me learn my way around the institution, but more importantly, she expressed genuine care for me and made me feel very welcome. That year was a weird year in many ways, because of Covid and also because it was my first year here. But Sara was great at giving me perspective and encouragement. There’s a freshness and vitality in the way that she relates to her colleagues that belies her 40-year career.” 

Denise Labieniec talks about having “worked with Sara in so many capacities in my time at Winsor. I remember being on committees with her years ago when she was department head the first time around and so looked up to her thoughtful and informed approach to leadership. I learned so much from the way she engaged (and still engages) with colleagues in discussions. Sara always listens deeply and considers multiple facets to an issue. Her creative and innovative thinking extends far beyond the art classroom to her work with curriculum, and she can easily spot the difference between a trend and real innovation—something I experienced time and again when working with her as director of studies…. Right before COVID, … Sara was a member of [a small group of faculty who helped us move school online] and brought her extensive expertise with online teaching to guide us. Her wisdom, clarity and vision were absolutely essential in putting together the plan that kept our academic community together during that very challenging time.”

So, back to that resume! In her 40 years, Sara has thoughtfully mentored new colleagues; helped shape our institutional response during times of great need, taught students in virtually every artistic medium we have; developing deep, meaningful relationships with students throughout their time here; inspired colleagues in and out of the department; and stayed connected with alums long past their graduation. It is a career built on excellence, creativity, curiosity, and love. 

Perhaps former Winsor Director Carolyn Peter said it best, years ago: “Sara Macaulay makes Winsor a better school each day.” 

Please join me in congratulating Sara Macaulay on an amazing 40 years at Winsor!