Woodstock Town Supervisor Bill McKenna declined to run for a fifth term this year, and local Democrats voted in late June for Anula Courtis, a two-term council member who ran her primary on a platform of transparency and community engagement. “My background in both the private sector and local government has taught me that real progress starts with trust, transparency, and a commitment to engaging people meaningfully in the decisions that affect their lives.” she says. “In Woodstock, that means creating space for open conversation, even when issues are contentious or complex.”
Courtis will certainly have her work cut out for her. Issues that arise in Woodstock tend toward complexity. And even when folks agree about a need for more housing, for example—the particulars of getting from point A to point B can get considerably contentious.
Take Zena Woods. Developers Evan Kleinberg and Eddie Greenberg bought 624 acres straddling the Woodstock/Ulster town line and originally came to the town proposing 191 units of housing, an 18-hole golf course, and a heliport.
“It was very much just an idea that we had, and we wanted to be transparent with the planning board and with the community, and share our idea,” says Kleinberg. “We got a lot of backlash. It was productive; it was the feedback that we were looking for at that time. And we realized very quickly that our idea was not what the town wanted there.”
That was in summer of 2023. The developers came back to the town in late 2024 with a proposal for a 30-lot subdivision with a recreation center and pickleball courts, scrapping the golf course and heliport. Complicating the situation from the start was the geography: the section of the parcel that the owners currently wish to subdivide is landlocked in the town of Ulster, and the only practical access is a private road running a little over a mile through the town of Woodstock. Abutting the parcel is the Woodstock Land Conservancy’s Israel Littman Sanctuary, and even the smaller proposal is not something the Conservancy folks want next door.
“It’s very clear that they’re going for their bottom line, and it’s very clear that they’re not thinking about the environment and the people who currently live here, and that’s just not fair to our community or to the people who actually need housing,” says Andy Mossey, executive director of the Conservancy. “At the end of the day, they’re not going to be fulfilling the need for the housing; it’s about their need to fulfill their bottom line and pull in people who can afford to live in extremely expensive homes.”
Concerns raised by the opponents include wetlands protection, water supply, traffic, and the provision of emergency services given the divided jurisdiction.
Kleinberg says that the original proposal included affordable housing; in the downsized subdivision, that math no longer works, but he’d still like to see a mix in which fancier homes help cover the cost of some that sell for under a million—in line, he observes, with the price tags of the existing homes changing hands. To solve the emergency services conundrum, they propose a homeowners association that would collect and render to Woodstock the same amount that those homeowners would be paying in taxes. Mossey says that homeowners associations are an alien concept in the neighborhood, and that the Conservancy doesn’t trust the developers’ stated intention to keep the 500 acres located in Woodstock undeveloped.
Both Woodstock and Ulster have expressed their desire to be lead agency in the state environmental review process, a question that the state DEC is expected to decide in the near future. The developers say their most recent appearance before the town planning board actually left them feeling encouraged; the opponents are still hoping the land can be kept wild and become part of Catskill Park, open to the public free of charge, like the Conservancy’s new 30-acre Rock Oak Preserve in West Hurley.
Rebuilding for the Long Haul
Another plan that’s been downsized is a new youth and community center at Andy Lee Field, a facility largely unchanged in 75 years. The first proposal included an indoor pool and gymnasium, and task force leader Ben Schacter admits that may have been overly ambitious. But he says the town still needs and deserves an upgraded, intergenerational facility, ideally with an outdoor pool, covered sports courts, and a dedicated farmers’ market space.
“Removing the indoor facilities will free up a ton of green space,” says Schacter. “Some people simply thought it would cost too much money, and I think that’s a very valid issue. We’re doing our best to continue to raise funds; we’ve raised over a million dollars in pledges so far, and we’re in the process of applying for grants. Most importantly, we’re not gonna spend any of this money ourselves—we are just an advisory committee to the town board. What they have promised is to hold a public referendum to decide if we should spend this kind of money, and that’s where we are right now.”
Courtis believes robust public discussion will shed light on the right way forward on these and other plans. “Collaborative problem-solving requires clear-sighted leadership that listens, builds coalitions, and makes decisions grounded in fairness and fact. It also means working with the right people, those committed to the greater good, to move things forward,” she says. “Not everyone will agree on every issue, and that’s okay. This isn’t a popularity contest. Our responsibility is to make informed, forward-looking decisions because people’s well-being and quality of life depend on it. When we act with respect, seek consensus where we can, and root our work in shared values, we build something lasting.”Possibly the most ironic debate in Woodstock has been the one about the acceptable volume of live music, a topic that a task force has been wrestling with since spring of 2023. Neil Howard, owner of live music venue Colony, thinks a sweet spot may have been found but he knows not everyone will concur. “No live music ever is not going to work, and a free-for-all seven nights a week won’t either,” Howard says.
“Somewhere around three or four is probably about right,” he continues. “We’re allowed to do patio and acoustic whenever we want and that’s great. We do medium-volume outdoor events on Fridays and Saturdays, and we have five big ticketed events a year. But some of the live music supporters feel things are too draconian, and then there are those who object to any audible music at all. People say that’s new folks from the city, but it’s largely not—it’s people who came here 40 years ago and now they don’t play anymore and they want silence. A couple of weeks ago we had a concert called Back To the Garden, a sort of highlight reel of covers of the original concert, Hendrix and so on. We got complaints—from someone who takes pride in saying ‘I’m from Woodstock,’ gets off on being from this famous town, but actually doesn’t want the thing that made it that way.” Regardless of those opinions, the Colony will welcome the Women of Reggae Fest, Joan Osborne, and an afternoon benefit, Democracy Rocks!, to their outdoor garden this month.
Summer is high season at Maverick Concerts, and its signature offering, the Chamber Music Festival is in full swing through mid-September. It’s been happening annually since 1916, back when the old guard at Maverick and Byrdcliffe Arts Colony got their own share of side-eye. It’s music director Alexander Platt’s 23rd season at Maverick, and he says things just keep getting better. “It’s a beautiful world within the beautiful world that is Woodstock,” he says. “We have a beautiful new green room; our Saturday family series is more vigorous than ever—it’s been free the past two years—and we’re thriving in our newfound tradition of ever more eclectic offerings—Saturday nights we have jazz and Americana; Sundays we showcase many of the world’s greatest string quartets. Young couples start out bringing their kids to the Saturday show and then a few years later, we’ll see the whole gang on Sunday for Beethoven. We’re just going from strength to strength, and every day is a joy.”
Platt hopes you’ll come out and listen, maybe grab a membership; this is no time, he says, to take Maverick for granted. “We suffered a real body blow when the $35,000 grant we were awarded from the National Endowment for the Arts was rescinded in March. Still, we get packed houses full of wild enthusiasm. We’re finding our path forward.”
From Drum Circles to Digital Journalism
Pathfinding is a very Woodstock trait. When the Woodstock Times was absorbed into the regional Hudson Valley One during the pandemic, Golden Notebook bookstore owner Jacqueline Kellachan began to feel that there might be room for a fresh source of hyperlocal news coverage. Since February the Overlook—staffed by folks with impressive journalistic careers in larger markets alongside passionate young reporters—is covering Hunter, Hurley, Olive, Saugerties, Shandaken, and Woodstock. “People are really loving the journalism and the focus on in-depth stories,” says Kellachan. “We bring them stories they don’t get elsewhere—a library fair in Olive, affordable housing in Tannersville—and we’ve seen our subscribers double since we launched. And people tell us they really, really look forward to getting that email from the Overlook every Friday.”
All over the region, pandemic lockdowns gave creatives—both new arrivals and longtimers—lots of time to think and conspire, followed by exuberant creative endeavors that now fuel new levels of fun. The trend shows no signs of slowing, and Woodstock is no exception. “Fourth of July was insane, just mobbed,” says Kellachan.
“I think that people love to come here because you can walk from one end of town to another and with maybe one exception, every business is an independent business,” she says. “And that’s just not something that exists in much of the United States, but here in the Hudson Valley, it does, and people love being in spaces curated by humans. I think that’s one of the longstanding attractions of Woodstock in particular—indie businesses, the Mowers Flea Market, drum circles on the Green. People will always be moaning about parking, of course, and traffic; I’d be sad if I didn’t hear those complaints.’
Twenty-year resident Craig Leonard, owner of restaurants Good Night and Silvia, has recently launched a new venture: Gemela, an all-day cafe, restaurant, and bar. “Gemela is very different, a breakfast and lunch cafe, not a full-service restaurant,” Leonard says. “Silvia and Good Night are established and thriving; Gemela just opened in June, and people are still finding out about us—and as they do, they’re enjoying the food and the space very much. I have a different partner for this one—my extremely talented sister-in-law, Lisa Choi—and the opportunity arose to showcase what she can do, and it’s beautiful.”
Leonard says the town is hopping. “I see no reason that shouldn’t continue. It’s a great, fun place to be. There have been controversies ever since Hervey White founded Byrdcliffe Arts in the early 20th century,” he says. “There’s always debate in a small town, where everyone has their own ideas of how it should be. But for our part, we just love having places where people can relax, kick back, and spend quality time together.”
With no Republican candidate on the horizon, Courtis seems firmly on track to become Woodstock’s first ever supervisor from the LGBTQ community, possibly leading its first-ever all-female board. Expect collaboration, and lots of it. “On topics like noise or policing, it’s essential to begin with honest dialogue: listening to different lived experiences, acknowledging frustrations, and structuring conversations so that everyone has a chance to be heard,” she says. “With challenges like housing affordability, the path forward has to be strategic and community-driven. That includes setting clear goals, from expanding affordable options to updating outdated zoning, and involving residents in shaping long-term solutions.”
This article appears in August 2025.
