By Taylor K. Long
Last week, the town of Windsor raised the Progress Pride Flag in front of the town’s municipal building for the first time. The woman behind the podium who welcomed people by name as they joined the celebration, the woman who raised the flag, the woman who proposed raising the flag in the first place, is Amanda Smith, a new member of Windsor’s selectboard.
Since joining the selectboard in March, Smith’s productivity and devotion to a more inclusive and welcoming Windsor community have been on constant display, from speaking at the town’s Black Lives Matter rally, to attending and speaking out at the Mt. Ascutney School Board’s special meeting regarding Windsor Principal Tiffany Riley’s decrying the BLM movement.
Photo by Taylor K. Long
Photo by Taylor K. Long
Photo by Taylor K. Long
Photo by Taylor K. Long
But Smith made a mark on Windsor well before she joined the selectboard. Last year, she founded the LGBTQ+ & Allies of Windsor, VT group, and not only initiated, organized, and hosted the town’s first Pride celebration, she pulled it together in less than two weeks, a truly remarkable feat.
Organizing the Pride event moved Smith to think about the positive impact she could have by getting involved with the community, so she decided to run for the selectboard. “I decided, it’s 2020, it’s the Centennial of the 19th Amendment,” she says, “What a beautiful way to honor my foremothers and throw my hat in the ring, and be part of the 250,000 by 2030 initiative put on by She Should Run.”
She finds inspiration through her four-year-old son, Eli, and her role as a mother. “What keeps me going and also keeps me balanced is my son,” she says. “I love him so much and everything I do is to make the world a better place for him, but I also make sure to take the time to enjoy that world with him.”
Getting involved in politics can be especially challenging for mothers, who often carry an inordinate role in caretaking for children, and receive myriad mixed messages and judgements regarding work-life balance. If you stay home with your kids, you’re not driven enough in your career, if you spend too much time at work, you’re not spending enough time with your family. Women are both told that we can have it all and that we can’t, because “having it all” means splitting your efforts and your focus. “It definitely can be difficult to find that balance, but it's possible and I think it's really important to say that because we need more moms in politics,” Smith says. “If you're reading this and you’re a mom who wants to get involved, reach out to me if you'd like, I would love to support you.”
Photo by Taylor K. Long
Photo by Taylor K. Long
Among Smith’s many priorities is making attending selectboard meetings more accessible, not only sharing recordings of the meetings, but encouraging people to attend, and potentially enabling people to stay involved in them online, even after in-person meetings resume. She also hopes to find a way to offer childcare during them, a major hurdle for women and caregivers.
Chris Goulet, who joined Smith as a new appointment to the selectboard in March, notes that there have only been three women on the Windsor selectboard since the ’80s: Donna Sweaney, who eventually became a state representative, current board chair Heather Preebish, and now, Smith. [Ed Note: Since this piece was published, we've been notified that there was a fourth woman on the Windsor selectoboard, Ilene Beattie.] Having known Smith for years, Goulet describes her as a “transformative and transitive energy,” and he’s grateful for her presence on the selectboard. “It’s just been tremendous and inspiring to see the work that she’s been able to affect in helping the community, in listening to the community and channeling that into meaningful conversation and discourse at higher levels,” he says. “She really is a force for good, and change. She leads with her heart, and we as a community will absolutely benefit from that.”
Goulet also believes that Windsor’s selectboard may be the youngest in Vermont, with Smith, Goulet, and James Reed all being under the age of 40.
Photo by Taylor K. Long
Photo by Taylor K. Long
Photo by Taylor K. Long
Photo by Taylor K. Long
Smith is clear that “it's not easy to be an ally,” she says, “but it's even harder to be a really good one.” It involves a lot of hard work, uncomfortable feelings, and confronting ugly histories. Smith is an outspoken advocate for telling the story of Dinah, who was kept as a slave in Windsor by Stephen Jacob in the late 1700s, despite slavery being illegal in the state of Vermont. When Dinah’s eyesight and health began to decline, Jacob forced her out, and she became a ward of the Town of Windsor. The town later sued Jacob over the expenses for her care, and the Vermont Supreme Court decided in Jacob’s favor, saying that it wasn’t possible for Dinah to be a slave because slavery didn’t exist in Vermont.
“Her story is so important,” Smith says, “Not only because we're giving her a voice now that she didn't have during her life, but also, these issues of racial injustice have not gone away.” Historic Windsor, Inc. recently installed a marker for Dinah at the old Jacob house, which they purchased in 2008, and hosted a talk about slavery in Vermont with UVM Professor Amani Whitfield last year, which Smith also spoke at. She’d like to see Dinah honored in Windsor in bigger ways, such as an official roadside historic marker, a memorial for Dinah in the Old South Cemetery (where she was known to care for children), and by renaming the nearby Jacob St. “I think often, people in the North, people in Vermont can think that this was a southern issue. Or those concerns aren't our concerns, but they are,” she says, “And when we face our history, accept it, we're better able to make solutions, and we're better able to listen to the people who have historically not been listened to.”
Photo by Taylor K. Long
Photo by Taylor K. Long
Smith’s vision of Windsor also includes more support for public arts and events, and drawing more young families and people to the town. She feels some in the Upper Valley may have an outdated view of Windsor. "We still have our core values that have always been here, but we have evolved with the time,” she says. “I think Windsor could benefit from some promotion and re-marketing.”
It’s safe to say that many of the town’s residents agree. In the wake of an increasingly online community due to Covid, selectboard members Goulet and Reed began a regular broadcast of updates on town happenings called Windsor Live. What began as a simple Facebook live stream will be adopted by Windsor on Air and the new Riverpower Podcast Mill, which produces several shows, like the horror series “Pulp from Beyond the Veil.”
As the town and its residents keep making space and showing support for these kinds of informative and creative outlets, events like the Black Lives Matter rally and the Pride flag raising—as well as the events at the Windsor Exchange, like Science Night and WoTown—that vision of Windsor becomes increasingly attainable.
“Amanda Smith has consistently shown that she is willing to stand up and take action to make our community a more open, affirming place for all residents,” says Windsor resident Davis McGraw. “In a cultural and historical moment when leaders seem more than happy to abdicate their responsibilities in the interest of comfort, Amanda models a higher standard of what leadership can and should be.”

June, 2020
Taylor K. Long is a writer, editor, and photographer based in Windsor, VT. Her work has appeared in The New York Times, The New York Press, New York Magazine, Bright Wall/Dark Room and more.
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