Woodstock’s newest deputy supervisor has only been in town 12 years. But he’s already a familiar face.
You might have seen him perform with Mambo Kikongo, Lindsey Webster or as Reggie Earls and the Hudson River Pearls, or you may have seen him volunteering for Family of Woodstock. He’s hit the ground running, with one Town Board meeting already under his belt.
“Bill (McKenna) called me over Thanksgiving. I was in Virginia. He asked me if I would consider it,” Earls said of becoming deputy supervisor. “He knows I love this town. I’m involved with the town.”
Earls said Supervisor McKenna got to know him through the town Democratic Committee, something he become involved in over the pat year.
“It’s not something I was expecting and it’s not something I sought,” Earls said. “I was honored that he thought of me. He’s someone that I respect. So it definitely meant a lot to me that he thought of me. I thought even more so because I’m not originally from Woodstock.”
The deputy supervisor oversees town functions and runs meetings if the supervisor is incapacitated or otherwise unable to perform his or her duties. Often, the role is assigned to an elected member of the Town Board, but it doesn’t have to be. Liam Kahn was Jeremy Wilber’s deputy when he was an intern at then-Congressman Maurice Hinchey’s office. More recently, Laura Ricci held the position while she was a member of the Planning Board, but not yet a councilwoman.
Non-elected deputy supervisors get a seat at the table and can provide input in matters, but cannot vote. The position can be used as a stepping stone for those not yet in elected office, though Earls said he hasn’t yet considered that possibility.
“I haven’t had any political aspirations at all. I’ve been getting involved this past year with Democrats and just getting plugged in a little bit more,” Earls said.
Earls was born and raised in Portsmouth, Virginia, and attended college at East Carolina University in Greenville, N.C. He started out as a music major, but switched to social work, then eventually made a connection to Woodstock.
“I became friends with an Episcopal priest and he got a job at St. Gregory’s in Woodstock,” Earls said. “He and his partner moved to Woodstock while I was in college and I came to visit and just loved it. I just loved the area.”
Earls returned a few more times while he was still in college, renting a home from friends. He finally moved to Woodstock permanently in 2006 after he graduated.
Earls is director of music, choir director and organist at the Dutch Reformed Church. For 9 years, he was music director at the Church of the Messiah in Rhinebeck.
He also works with Family of Woodstock, filling in at a transitional living program for adolescents called Midway. He has worked for Mental Health Association of Ulster County and in the foster care field as a specialist.
Reggie serves on the board for Angel Food East, an organization based in Kingston that provides meals for Ulster County residents who are chronically ill.
Like many, Earls saw the way things were going on a national level and decided it was time to become involved locally. That’s when he joined the town Democratic Committee.
“(County Legislator) Jon Heppner called me and there were some openings with the group. He said why don’t you come check it out and see what you think,” Earls said. “I felt if you don’t get involved, then you’re not really a part of the process.”
For now, Earls is just getting acquainted with the way the town’s wheels turn. “I imagine in the beginning I’m going to do a lot of listening. I don’t have a set agenda of things at this point,” he said. “I think as I spend more time with the Town Board and understanding some more functions of the town and seeing where I can be of help.”
Join the family! 
