Sierra Sullivan joined Harborfest’s board of directors over two years ago — she wants to help make the festival ‘feel more alive, more current, more connected.’ She is among the candidates competing to become the festival’s next executive director
By Stefan Yablonski
Charlotte Sullivan, wife of former Oswego Mayor John T. Sullivan Jr., was the driving force behind Harborfest in its infancy. She secured the annual fireworks spectacular, which continue to be the highlight of the festival to this day.
Today, their daughter, Sierra, continues their vision.
“My parents believed in this festival, this community. It’s a responsibility and privilege to carry that forward; continuing their legacy, building something future generations will be proud to step into,” Sierra said. Currently a board member, she is also under consideration to become the new executive director.
Charlotte Sullivan died on Nov. 23, 1999; John T. Sullivan Jr. on Nov. 27, 2023.
“I come to Harborfest with a mix of event production, film production, marketing, business, publishing and community-building experience,” Sierra said. “I have spent most of my adult life building things, producing experiences and bringing people together. So, when I started spending more time back in Oswego, I could immediately see both the potential here and the opportunity to help. Harborfest has been part of my life for a long time through my family, but coming back as an adult gave me a very different perspective. I was no longer just seeing it through nostalgia. I was seeing what it could become in this next era for the city.”
She joined the Harborfest board about two and a half years ago, shortly after her father died. In the final months of his life, he strongly encouraged her and her husband to consider getting involved.
“He could see that Oswego was beginning to shift, with new energy, new opportunity and a lot more on the horizon,” she said. “He felt that the skills I had built over the years could be put to good use here — he specifically mentioned Harborfest as a place that could use fresh support.”
At first, she had no plans to get involved.
“But while caring for him during his illness, I ended up spending more time in Oswego than I had in years and I really fell back in love with the city. After he passed, I started having conversations with key people in the city [the mayor, the Harborfest director at the time and local businesspeople], sharing ideas and looking for ways to help. That eventually led to my husband and me joining the board and rolling up our sleeves,” she explained.
Bringing the mojo back to the fest
“For me, bringing the mojo back is not about changing what people already love about Harborfest. It is about building on that foundation and making the festival feel more alive, more current, more connected to the full energy of Oswego. Yes, absolutely,” she said. “A lot of the newer board members, myself included, have been focused on modernizing systems that were badly outdated, things like the website, social presence, branding, communications and overall infrastructure. That work matters because it gives us a stronger base to grow from.”
Creatively, she said she would love to see more arts and culture, a broader range of music, more immersive and experiential programming and more ways for the community itself to participate in shaping the festival.
“I have been especially interested in bringing in more jam band culture because it has a strong following, a great vibe and the kind of audience that travels, stays, spends and engages deeply with a festival experience,” she said. “I also want Harborfest to connect more directly with the rest of Oswego. One of the original purposes of the festival is to showcase the city and drive tourism. If everything happens only in the parks, visitors don’t fully experience what Oswego has to offer. That is why I am excited about efforts like officially weaving downtown activations into Harborfest, including things happening around Pocket Park and the Water Street area that local SNAX owner Graham Barney is helping us to produce. That creates more opportunity for local merchants, restaurants and businesses to benefit and to become part of the experience.”
A tradition and an opportunity
“I also think there is room to bring in more wellness, workshops, interactive offerings and things that invite people to do more than just watch bands and walk through vendors,” she added. “Oswego has so much more to showcase now, from art and music to fitness, healing, food and local entrepreneurship. Harborfest can be a bigger, richer gateway into the city itself.
“At the end of the day, I see Harborfest as both a beloved tradition and a huge opportunity. The goal is to honor what it has been while helping it evolve into something that feels fresh, exciting and reflective of where Oswego is headed.”
Growing up Harborfest
“My husband, Rono [short for Ronald], is both my life partner and my longtime business partner. We have been in business together since before we were married and today we co-lead Eden World, a relationship-based personal development company for committed couples,” she said. “He also grew up in Oswego. So, this community and Harborfest are deeply personal for him too. From a young age, he was involved in musical performance and played Harborfest with a few different bands in the early days. He has been an event producer, creative, designer and professional musician for most of his life. Over the years he has worn many hats across creative and entrepreneurial work. In addition to running Eden World with me he is also currently working with a crypto banking and finance software startup called Arqitech.”
Growing up, what she loved most about Harborfest was the way the whole community came together to build it. It felt like everyone had a hand in it and everyone understood that this festival had the power to put Oswego on the map, she said.
She got to witness the different stages of it growing from an idea her parents had into a major community tradition and that was powerful on both a civic and personal level.
“I also saw firsthand how much volunteer energy, support and belief it took to make Harborfest what it became in its heyday,” she said. “As I got older and went away to college, my perspective expanded. I started attending more festivals and became really interested in the way art, music, creativity and community can all come together in one experience. I went to my first Burning Man in 1998 and that opened my eyes to a completely different kind of creative and communal expression. I also watched my mom build her consulting work around fundraising and festival strategy and saw how skilled she was at inspiring people to support something bigger than themselves for the good of the community. So, while I would not say I have mainly been a concert person, I have attended a lot of festivals over the years, especially music festivals and community-centered events. What inspires me most is not just the music itself, but the bigger experience around it, the culture, the creativity, the gathering, and the possibility of what a festival can spark in a city.”
Help Wanted: Executive Director
Harbor Festivals is looking for a new director. Dan Harrington, who has served as executive director since January 2023, resigned in February. He agreed to stage this year’s Harborfest, however.
Sierra Sullivan, the daughter of the festival’s main driver force, Charlotte Sullivan, said she is in the running for the position.
“In short, yes, I have submitted my resume and am being considered for the position,” Sullivan said. “I’m excited about the possibility. I believe my professional background, community relationships and experience rallying people around a shared cause would allow me to be a strong asset to Harborfest, its fundraising initiatives and the role of executive director.”
A five-member Harbor Festivals committee is conducting a full search to find a new director, she said. The committee overseeing the search is led by Jennifer Hill and Chuck Handley.
“I really do want the job. I have a lot of great ideas and initiatives to put into play for the future of the fest. And so many people, resources and connections that I can bring into the mix for support,” she said. “I feel it would be silly for them to choose anyone else — but again, I respect the process and am hoping for the best outcome. I respect that process. There may be another applicant who ends up being the best fit for the organization at this time. If that is the case, I will stand behind that — as I want what is best for the fest. I will continue to serve as an active member of the board.”
